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Transaction Retrospection

Flashback: The Spring 2014 Contract Spat Between Max Scherzer & The Tigers

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In the 2013-14 offseason, the Tigers were still riding high. Despite some postseason disappointments, the organization had run off three-straight AL Central titles and seemed poised for more. It also had a slate of big-time veterans coming ever closer to free agency.

The top priority, it seemed, was emergent ace Max Scherzer. He had seemingly supplanted Justin Verlander as the top dog on one of the best rotations in recent memory. But free agency beckoned at the end of 2014, Scherzer’s age-29 season.

You may recall that the Tigers ended up making a major long-term deal … but not with Scherzer. (No doubt we’ll write more on that one at some point soon.) Instead, club and player ended up engaging in a somewhat terse exchange of statements to the press at the end of camp, setting the stage for Scherzer’s ultimate departure.

After showing so much tantalizing ability over the years, the former first-round draft pick finally put it all together in 2013. Scherzer spun 214 1/3 innings of 2.90 ERA ball, racking up 10.1 K/9 against 2.4 BB/9 and leading the league with a 0.970 WHIP. Scherzer not only nabbed his first All-Star appearance, but secured his first Cy Young Award.

The Tigers spent big and went for it under long-time owner Mike Ilitch, with veteran exec Dave Dombrowski swinging deals from the GM seat. Pursuit of an extension with Scherzer was inevitable.

Trouble was, Scherzer had taken his time turning into a complete pitcher. By the time the team was ready to place its bet on his future, he had ample leverage. And he had the game’s foremost lever puller running his negotiations: super-agent Scott Boras, long known for bringing his top clients to the open market.

Early-offseason moves freed some payroll availability; Dombrowski told MLBTR’s Zach Links the flexibility would make a Scherzer extension “more possible.” The sides were able to line up on a record-setting arbitration raise, which seemed generally promising. Scherzer indicated that he’d like to reach agreement on a deal to stay in Detroit for the long run.

And then came … a truly bizarre, late-spring exchange. We’ve occasionally seen teams issue statements when negotiations with a superstar fail to culminate in an agreement. But rarely are they so transparently salty as the one the Tigers unfurled …

“The Detroit Tigers have made a substantial, long-term contract extension offer to Max Scherzer that would have placed him among the highest paid pitchers in baseball, and the offer was rejected. As we have reiterated, it has been the organization’s intent to extend Max’s contract and keep him in a Tigers uniform well beyond the 2014 season. While this offer would have accomplished that, the ballclub’s focus remains on the start of the upcoming season, and competing for a World Championship. Moving forward there will be no further in-season negotiation and the organization will refrain from commenting on this matter.”

Well, then! Boras, naturally, responded. He wasn’t quite so spiteful, but certainly landed his own well-placed shot that left no doubt as to his views on the equal standing of the bargaining parties:

“Max Scherzer made a substantial long-term contract extension offer to the Detroit Tigers that would have placed him among the highest-paid pitchers in baseball, and the offer was rejected by Detroit. Max is very happy with the city of Detroit, the fans and his teammates, and we will continue negotiating with the Tigers at season’s end.”

So it seemed both sides had made their offers; neither proved amenable to further compromise. It emerged that the Tigers’ best offer was a match of the extant comparable of record: the six-year, $144MM Cole Hamels extension with the Phillies. The warring statements drew mixed reactions from the pundit class, but the consensus was that this number was never particularly likely to budge Boras and Scherzer.

Rather than bowing to worry over the season separating him from free agency, Scherzer took out an insurance policy. He was nearly as good in 2014 as he was in the season prior, landing a fifth-place Cy Young finish, obviating the need for that policy, and setting the stage for a proper bidding war. While there was indication at times that the Tigers remained involved, the team showed tepid interest and was not a finalist when push came to shove.

Scherzer, of course, signed a huge contract with the Nationals. Though the face value of $210MM didn’t account for deferrals, it handily topped the prior Tigers offer. Perhaps it was just as well for the Detroit organization. While the club was successful again in Scherzer’s final year, it crumbled in 2015, with Dombrowski stunningly departing after the trade deadline. Then again, Scherzer’s ongoing dominance made even that monster contract a relative bargain. Had the Tigers gone higher in their extension offer and managed to secure his services for the long haul, Scherzer would’ve been a nice trade chip to cash in and jump-start the rebuild.

Photo courtesy of USA Today Sports Images.

Transaction Retrospection: Elvis Andrus’ Extension

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Contract extensions have been a key part of Jon Daniels’ team-building strategy over his 14+ years as the Rangers’ general manager, and the richest of those extensions was completed seven years ago today.  Elvis Andrus agreed to an eight-year, $120MM contract that also contains a $15MM vesting option for the 2023 season.

The new deal began with the 2015 season, which would have been Andrus’ first free agent year.  Andrus was already signed to a previous extension — a three-year/$14.4MM pact for the 2012-14 seasons, which were Andrus’ three arbitration years — and thus Texas needed to make a sizeable investment to keep Andrus off the open market.  As MLBTR’s Steve Adams noted at the time of the deal, “Scott Boras has managed to secure the largest extension ever for a shortstop in terms of new money,” which was perhaps a necessary step given that Boras usually advises his clients to test free agency.  (In fact, the Andrus deal has been cited for years as one of the relatively few examples of a Boras Corporation client signing a long-term extension that covers free agent seasons.)

At the time of the deal, it’s quite possible the Rangers felt they would ultimately be on the hook for only the first four years (and $62MM) of the extension.  Andrus had opt-out clauses after both the 2018 and 2019 seasons, and as deep as a week into the 2018 campaign, he looked like a strong candidate to exercise that first clause given his improved offensive production in 2016-17.  However, a fractured elbow cost Andrus two months of the 2018 season and he never really got on track after the injury, thus informing his decision to stick with Texas in 2019.

Last season, Andrus just flat-out struggled, hitting .275/.313/393 (76 wRC+, 78 OPS+) over 648 PA, with a career-low 5.2% walk rate and a major lack of quality contact, as per his Statcast numbers.  In the wake of that poor season, Andrus again chose to pass on his opt-out clause, leaving Texas owing the shortstop $43MM through the 2022 campaign and now not really knowing what to expect from Andrus performance-wise over those three seasons.

Such risks are baked into any extension, of course, and it’s worth noting that Andrus’ hitting potential was a question mark even back at the time of his 2013 deal.  Though he had been a highly-touted prospect (Baseball America ranked Andrus as the 19th-best prospect in the sport prior to the 2008 season) during his time in the Rangers’ farm system, Andrus’ minor league numbers weren’t overly impressive.  Even at the big league level, he hit only .275/.342/.353 over his first 2591 MLB plate appearances.

That said, 2012 marked Andrus’ best offensive showing to date, as he hit .286/.349/.378 over 711 PA and reached the AL All-Star roster for the second time in his career.  And, it’s unfair to say that Andrus wasn’t a valuable offensive player early in his career, considering that his solid average and OBP were augmented by superb speed and baserunning.  Combine these skills with a solidly above-average glovework at shortstop, and it’s easy to see why Texas felt comfortable making a long-term bet on Andrus’ future.

Had that extension not been signed, Andrus would have been a 26-year-old free agent hitting the free agent market in the 2014-15 offseason.  There wasn’t much in the way of premium middle infield talent available that winter, so even though Andrus didn’t do a ton to elevate his stock over the 2013-14 seasons, his young age and hints at further productivity could have still potentially led to a nine-figure contract.  An Andrus free agent deal could have been something of a forerunner to Jason Heyward’s deal with the Cubs a year later, with a team choosing to pay a premium for a 26-year-old, non-elite offensive player based on their overall skillset and future breakout potential.  Heyward had a much better hitting track record than Andrus, so the shortstop wouldn’t have gotten anywhere near the $184MM and eight years Heyward got from the Cubs, though it isn’t a reach to guess that a team could have given Andrus a six-year commitment.

Though it isn’t known whether Andrus will be able to get back on track in 2020 (if there is a season) or beyond, the uncertainty of the back end of his deal doesn’t mean the extension was a mistake for the Rangers.  As per Fangraphs, Andrus has already delivered $85.8MM worth of value over the first five years of the contract, surpassing the $77MM he has earned in real-life money.  Andrus was a major contributor to the Rangers’ AL West titles in 2015 and 2016, and while he has never matched his offensive peaks of 2016 and 2017, his sheer durability has also been a big point of value — the fractured elbow is the only significant injured list stint of Andrus’ entire career.

Indeed, that wayward pitch from Keynan Middleton (on the second-last at-bat of a 7-2 Angels win over the Rangers on April 11, 2018) might end up being the real what-if moment of Andrus’ tenure with the Rangers.  Had Andrus gone on to match his 2016-17 numbers in an uninterrupted 2018 season, he would surely have opted out of his contract and, even in the slow-moving 2018-19 free agent market easily topped the four years and $48MM left on this Texas deal.  In such a scenario, the critics currently bemoaning the Andrus extension would probably have then been criticizing Daniels for negotiating an opt-out clause into the deal in the first place.

Andrus is a notable question mark for a Texas team that is looking to turn things around after three losing seasons.  While the 2020 season could end up being a wash, getting one more solid year out of Andrus in 2021 or 2022 could be enough to mark down the extension as a win for the Rangers in the eyes of the general fanbase.  Even if 2019 is the beginning of end for Andrus as a productive regular, he has still done enough over the course of his contract to make it a decent return for the Rangers, even if that hoped-for leap into superstardom for Andrus never happened.

Transaction Retrospection: An Arizona-Seattle Blockbuster

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MLBTR’s Steve Adams just recapped the notable trades that Mariners general manager Jerry Dipoto has made dating back to his hiring late in the 2015 season. That was an unenviable task when you consider the eye-popping amount of deals that Trader Jerry has swung since he arrived in Seattle. One of Dipoto’s most significant moves so far came on Nov. 23, 2016, when the Mariners and Diamondbacks made a trade that will likely impact both franchises for the foreseeable future.

The Mariners sent right-hander Taijuan Walker and middle infielder Ketel Marte to the Diamondbacks for middle infielder Jean Segura, outfielder Mitch Haniger and lefty Zac Curtis. The only member of the quintet who hasn’t established himself in the majors is Curtis, who pitched 38 innings in the bigs from 2016-18 but is now a free agent after the Rangers released him last July. On the other hand, Walker, Marte, Segura and Haniger have all enjoyed at least some success at the MLB level.

Walker, once a blue-chip prospect, hasn’t really lived up to the hype thus far. After a so-so run with the Mariners, he did well for Arizona in 2017, throwing 157 1/3 innings of 3.49 ERA/4.04 FIP ball. Unfortunately, injuries have cut down Walker since then. He underwent Tommy John surgery early in 2018, forcing him to miss almost all of that season, and then made just one appearance last season as he recovered from TJS and battled shoulder problems. The 27-year-old is now back with the Mariners on an inexpensive contract, so it’s clear that the acquisition didn’t work out as hoped for the Diamondbacks.

On the other side, the Marte pickup has gone swimmingly for Arizona. Marte was not the headliner in the deal at the time, but he’s a former top-100 prospect who has emerged as one of the majors’ stars during his short MLB career. The switch-hitting Marte, now 26, had his struggles in his first season as a D-back, but that didn’t stop GM Mike Hazen from extending him on a five-year, $24MM guarantee going into 2018. That decision has worked out beautifully for Arizona, which benefited from Marte’s 2.6-fWAR effort in 2018 and far more from his 7.1-fWAR showing last season. Marte divided his nearly MVP-caliber 2019 campaign between second base and center field – positions that were sore spots for the Mariners.

The Mariners miss Marte, but that doesn’t mean they came away empty-handed in this swap. As noted earlier, they got back Walker on a low-cost pact that may or may not pay dividends. Segura gave the team two productive seasons before it traded him to the Phillies in a deal for shortstop J.P. Crawford, who has a chance to end up as the M’s long-term answer at the position. And then there’s Haniger, who thrived from 2017-18 before a gruesome injury (a ruptured testicle) deprived him of 99 of 162 games in 2019. Haniger was not viewed as a can’t-miss prospect when the trade went down, but he ran roughshod over Triple-A pitching and has held his own in the majors when healthy. He’s under control through 2022, so a healthy version could either continue as an asset for the rebuilding Mariners or wind up as a valuable trade chip.

Adding everything up, this counts as one of the most fascinating deals of the past few years. Both sides landed good players, but Marte has clearly been the most valuable piece to this point. The Marte addition is among the reasons D-backs GM Mike Hazen’s trade history has gone over so well.

Transaction Retrospection: Reds Rob Marlins

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We’re approaching the four-year anniversary of an under-the-radar Reds move that has paid and could continue to pay massive dividends for the franchise. On April 1, 2016, the Reds claimed right-hander Dan Straily off waivers from the Padres. At that point, Straily was coming off an up-and-down few years divided among the Athletics, Cubs and Astros, and he spent the vast majority of the 2015 campaign as part of Houston’s Triple-A affiliate. But the Straily pickup proved to be incredibly shrewd for Cincinnati, with which he overcame unimpressive underlying metrics to post a 3.76 ERA across a career-high 191 1/3 innings in 2016.

As a team, the Reds didn’t capitalize on Straily’s presence, winning a mere 68 games and finishing with more losses than wins for the third straight year. They still haven’t registered a .500 or better season since then, though the effect of taking a low-risk flier on Straily a few years back could be felt for a significant amount of time. After all, on the heels of his solid season as a Red, they flipped him to the Marlins in January 2017 in what’s arguably one of the biggest heists in recent baseball history.

In exchange for Straily, the Reds received three players – a pair of righties, Luis Castillo and Austin Brice, as well as outfield prospect Isaiah White. Brice didn’t amount to much in Cincinnati (he actually spent last season back with the Marlins and is now a member of the Red Sox organization), while the 23-year-old White hasn’t advanced past the Single-A level yet.

On the other hand, Castillo has become a gem – a hurler the Marlins no doubt rue trading at all, let alone for someone who was an unspectacular performer in their uniform. Straily was a Marlin from 2017-18, both losing seasons for the club, and pitched to a 4.20 ERA during that 304-inning span. The Marlins wound up releasing him heading into last season, which proved to be a disastrous year in the Orioles org for Straily. He’s now with the Lotte Giants of the Korea Baseball Organization.

Meanwhile, Castillo has morphed into an electrifying major league starter. After a respectable first two seasons in Cincy, the heat-throwing Castillo truly came into his own in 2019. The 27-year-old pitched to a 3.40 ERA/3.70 FIP with 10.67 K/9 and 3.73 BB/9 across a a personal-best 190 2/3 frames. Along the way, Castillo ranked second among all qualified starters in groundball percentage (55.2) and fourth in swinging-strike percentage (15.9), placing him between Cy Young winners Justin Verlander and Jacob deGrom. And Statcast loved Castillo’s work, ranking him near the top of the league in several important categories.

The fact that Castillo has evolved into such a standout isn’t wholly surprising. Remember, when the Marlins parted with Castillo, he was regarded as one of their handful of best prospects. Baseball America posited then that Castillo, who was coming off a season of stellar production at the High-A and Double-A levels, had mid-rotation potential. Nevertheless, despite his upside, it was the second time the Marlins had agreed to part with Castillo. They previously tried to send him to the Padres in a notable July 2016 trade, but they got him back after fellow righty Colin Rea’s medicals proved problematic. Had the Castillo aspect of that deal gone through, it also would have blown up in Miami’s face.

It seems fair to say that the Marlins did not properly value Castillo while he was with the organization. The Reds are profiting from that right now. In Cincinnati, Castillo currently finds himself as an integral piece of a quality starting rotation that could help the Reds push for a playoff berth this year (if there is a season). Castillo still has another pre-arbitration campaign left and the Reds have the ability to control him through 2023, making him all the more appealing. If the Reds are going to return to prominence in the near future, there’s a good chance that the Castillo trade will have something to do with it.

Photo courtesy of USA Today Sports Images.

Transaction Retrospection: Jose Quintana/Eloy Jimenez Trade

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Yesterday marked the one-year anniversary of Eloy Jiménez’s MLB debut. With that in mind, it’s an interesting time to look back at the blockbuster crosstown deal that brought the 23-year-old slugger to the South Side.

Jiménez wasn’t the headlining name of that July 2017 swap. That was José Quintana, with good reason. The southpaw had emerged as one of the game’s most consistent, reliable starters. True, he always played second fiddle to Chris Sale, but he was perhaps the game’s preeminent #2. Over the three-plus seasons preceding the deal, Quintana combined for a 3.47 ERA/3.31 FIP with no injury history to speak of. Equally as appealing, the hurler was controlled at well below market rates through 2020 thanks to an early-career extension.

The appeal for the Cubs was apparent. They had a superlative position player core that had carried them to the 2016 World Series. The starting rotation was already a strength, but one with some question marks on the horizon. Jake Arrieta and John Lackey were each approaching free agency, and it was fair to wonder for how much longer Jon Lester could post ace-level production. Locking in a cheap, young rotation stalwart like Quintana made perfect sense for that season and beyond.

It came at a hefty price. Jiménez, Baseball America’s #14 prospect entering that season, centered the package for the White Sox. Alongside him came another top 100 prospect, flamethrowing right-hander Dylan Cease. It was easy to see the South Siders’ thinking, too. Never able to build a competent roster around Sale, Quintana, Adam Eaton and José Abreu, the Sox had already pivoted to a teardown. Abreu stuck around, but the rest of the core was shipped off for future assets. It was a fascinating, if mutually-understandable swap, with the clubs’ crosstown rivalry no doubt adding intrigue. How have things actually played out?

To some extent, as expected. Quintana has remained remarkably durable and taken the ball every fifth day. That’s been especially useful for a team whose concerns about its long-term pitching outlook have generally proven true. Lester, Kyle Hendricks and Quintana have each been dependable, while big ticket free agent Yu Darvish has had some extreme highs and lows.

Despite a deluge of recent early-round picks on college arms, though, the Cubs haven’t established any sort of pitching pipeline from the farm system to supplement that quartet. On the one hand, that lack of cheap, in-house pitching makes acquiring Quintana all the more meaningful. Yet it’s also played some role in keeping the Cubs from reaching the dynastic heights some had anticipated.

Since the deal, the Cubs have been solid, but not quite at the level one could’ve reasonably hoped for. That characterization also applies to Quintana himself. The Colombian lefty has given the Cubs 400+ innings of 4.23 ERA/3.95 FIP ball. That’s about league average production on a rate basis. With his exceptional durability, he’s a valuable pitcher, especially relative to his contract. But he hasn’t pitched at the level he showed on the other side of town. Now 31, Quintana’s entering the final season (assuming there is a season) of the aforementioned extension. He’s a plausible but uncertain candidate for a qualifying offer next winter, which could allow the Cubs to add a draft pick.

Even if Quintana does net a compensatory pick, that player won’t project to be anywhere near the level of Jiménez. (That, of course, is what the Cubs expected, since there was always going to be a high price to pay for a pitcher of Quintana’s caliber). Not only did Jiménez continue to thrive in the White Sox’s system, he’s already found major league success.

Last season, Jiménez hit .267/.315/.513 (116 wRC+) with 31 home runs in 504 plate appearances. He’s not without his flaws; he didn’t rate well in left field and could perhaps stand to be a little more patient at the plate. Yet there’s no questioning Jiménez’s massive power upside, and he certainly looks the part of a potential middle-of-the-order force. Clearly, the White Sox expect him to be just that, having inked him to a $43MM guarantee that could keep him in Chicago through 2026. So continues the long line of early-career extensions the organization has amassed in recent years. Those deals (Quintana’s included) have paid huge dividends on the whole.

Cease, too, has a shot at emerging as a long-term asset. He raised his stock immediately after the trade with a strong season and a half in the minors. That didn’t translate in his first 14 MLB starts last season, but there are things to dream on. Cease posted a solid 24.9% strikeout rate as a rookie while averaging 96.5 MPH on his fastball. His is a higher-variance profile than Jiménez’s, but the Sox surely hope he can emerge as a useful arm in the near future, even if as a reliever.

With the benefit of hindsight, it’s probably fair to say the Cubs wouldn’t make this deal again. It was a perfectly defensible move at the time, and Quintana has capably filled a key need on the roster. It’s not a disaster, as a few of the front office’s free agent moves have been. But Quintana’s slight regression on the North Side, combined with Jiménez’s continued blossoming offensively, looks to have tipped the scales in the White Sox’s favor.

Revisiting The Chris Sale Extension

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The Red Sox were as busy as any team during last spring’s extension flurry, inking a pair of star players to long-term deals that kept them out of the 2019-2020 free agent market.  One of the extensions was a six-year deal with Xander Bogaerts worth $120MM in guaranteed money, a contract that now looks like a pretty sound investment given how Bogaerts followed up a strong 2018 season with an even better 2019 campaign.

The other extension is already off to a rough start.  Chris Sale signed a five-year, $145MM pact covering the 2020-24 seasons, with a club/vesting option for the 2025 campaign worth at least $20MM.  After vastly outperforming his early-career extension with the White Sox (which ended up as a seven-year, $59MM deal once both option years were exercised), Sale now had a new deal that better reflected his status as one of the better pitchers over the last decade.

Exactly one year after that extension was signed, however, the deal looms as a significant misfire for the Red Sox on a couple of different levels.  The club announced on Thursday that Sale would be undergoing Tommy John surgery, which will keep him out of action for whatever becomes of the 2020 season and, in all likelihood, around half of the 2021 season.  The surgery comes on the heels of Sale being shut down last August due to elbow inflamation, and while a platelet-rich plasma injection and some months of rest looked to have the left-hander back on track earlier this winter, Sale was shut down again earlier this month after suffering a flexor strain.

In the short term, this means Boston loses its best pitcher for 2020.  It is a major blow to a rotation that was only okay in 2019, and already had lost David Price after the Sox traded the veteran southpaw and Mookie Betts to the Dodgers in February.  While Sale could conceivably get back to something close to his old form post-surgery and still pitch well over the rest of his contract, the Betts/Price trade plays a critical role in evaluating the big-picture impact of Sale’s extension.

As much as Red Sox ownership has tried to deny it, the luxury tax was clearly a major reason the team was willing to part ways with Betts and Price.  Between moving Betts’ $27.7MM salary and half of the $96MM remaining on Price’s deal, the Sox have gotten themselves under the $208MM Competitive Balance Tax threshold, with Roster Resource projecting a current tax number just shy of $196MM for the 2020 Red Sox.

After two seasons of tax overages, getting under the CBT limit in 2020 would save the Red Sox millions in future tax payments, and theoretically allow them to spend past the threshold again as early as 2021 with only a minimal “first-timer” penalty attached.  As many Boston fans angrily noted over the winter, of course, trading Betts was a pretty extreme measure to achieve these luxury tax savings, and it’s a measure that could have well been avoided had the Red Sox not spent so much money elsewhere….for instance, on Sale’s extension.

Due to deferred money and the structure of the extension, Sale’s contract has a luxury tax number of $25.6MM per season from 2020-24.  Boston’s overall luxury tax payroll stood at roughly $236.3MM at the start of November, so subtracting Sale’s salary would have dropped their figure to $210.7MM, already within shouting distance of the $208MM threshold.  From that point it would’ve been much easier for chief baseball officer Chaim Bloom to make few more cuts and duck under the $208MM line without having to move Betts or Price.

Sale isn’t the only problematic salary on Boston’s payroll, of course, as the four-year, $68MM free agent deal Nathan Eovaldi signed last offseason is also looking questionable after Eovaldi’s injury-plagued 2019.  That said, the Red Sox were far from the only team who thought Eovaldi turned a corner in his breakout 2018 campaign, and they had to outbid the market to re-sign him.

In Sale’s case, the Sox didn’t necessarily have to pursue that extension, particularly given that a few red flags were already apparent.  Sale lost some effectiveness down the stretch in the 2017 season, and had an even shakier ending to his 2018, as shoulder problems limited him to just 17 regular-season innings after July 27 of that year.  The Red Sox were as judicious as possible in spacing out Sale’s appearances during the postseason, when he posted a 4.11 ERA over 15 1/3 innings en route to Boston’s World Series championship.

While Sale had been a very durable pitcher for the bulk of his career, seemingly running out of steam in consecutive seasons should probably have been enough to give the Red Sox some pause before guaranteeing him $145MM through his age 31-35 seasons.  As The Boston Globe’s Peter Abraham recently noted, the Sox may have been motivated to keep Sale out of a lingering regret over the Jon Lester situation from 2014, when the team was perhaps too rigid in extension talks prior to Lester’s final season under contract, which led to Lester being dealt to the Athletics at midseason and then going on deliver several more fine years after signing with the Cubs.

Abraham argues that waiting until after Sale’s final season could have been the more prudent decision for the Sox, as they would have had the added information of Sale’s 2019 numbers.  While the elbow injury was the biggest concern, Sale’s 36% hard-hit ball rate was the highest of his career, and his average fastball velocity dropped by 1.5 mph (to 93.2) from his 2018 speed.  Sale’s 2019 season was the worst of his ten-year MLB career, though given his high standards, a “bad” Chris Sale season was still very solid — a 4.40 ERA, 5.89 K/BB rate, 13.3 K/9 over 147 1/3 innings, and a wealth of advanced metrics (3.39 FIP, 2.93 xFIP, 3.00 SIERA) hinting that Sale’s 4.40 ERA was the result of some bad luck, such as a 1.47 HR/9 that far surpassed his previous career high.

Would this platform year have been enough to make Sale a big player in free agency?  We saw multiple top arms score larger-than-expected contracts this winter, though none of Gerrit Cole, Stephen Strasburg, Madison Bumgarner and company had a mid-August shutdown hanging over their heads.  It’s probably safe to assume that Sale would have still landed a pretty sizable multi-year contract if he had been a free agent, though that also assumes he would have tested the market at all.  His elbow injury could have led to Sale accepting a one-year, $17.8MM qualifying offer to remain in Boston, in the hopes that he’d return to better health in 2020 and deliver a prime season that would lead to a bigger deal in the 2020-21 offseason.

Adding another wrinkle to the mix, perhaps the Red Sox don’t even issue Sale a QO in this scenario out of a concern that he might accept it.  Boston’s approach to payroll seemed to shift radically from the start of the 2019 season to the end, as president of baseball operations Dave Dombrowski was fired and eventually replaced with Bloom, who was under that rather clumsily-issued edict to trim salaries.  In the wake of Sale’s 2019 season, perhaps the Red Sox would’ve been comfortable just letting Sale walk entirely, thus removing one more contractual concern from their books.

A major-market team like the Sox can weather a big contract not working out, but the franchise’s self-imposed desire to avoid the luxury tax suddenly puts many of the big deals of the Dombrowski era (the Sale extension, plus the signings of Price, Eovaldi, and maybe even J.D. Martinez considering the sheer dollars involved) under the radar.  This being said, blaming Dombrowski for Boston’s financial situation is unfair, as these nine-figure deals aren’t happening without the green light from ownership.

Sale’s extension is a prime example of how no transaction exists in a vacuum, as every signing/extension/trade/release/etc. is itself a response to some other move, and also sets off a chain reaction of other moves.  As Abraham pointed out, who knows if Red Sox ownership makes such a move if they had acted differently with Lester all those years ago, or if maybe Sale (or Price, or Eovaldi, or even Dombrowski) ends up in Boston whatsoever if the Sox had still had Lester in their rotation.  Unfortunately for Sale and the Red Sox, the second-guessing over the extension will continue at least until the southpaw can finally get back on the mound.

Transaction Retrospection: Joe Mauer’s Extension

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Though negotiations between J.T. Realmuto and the Phillies are currently on hold, the idea of a contract extension between the two sides has been gestating for months.  As such, there has already been a lot of speculation about how a Realmuto deal (if one is reached) will shake up the pay scale of catcher contracts.  The latest reports indicated that Realmuto was looking for an extension that would pay him more guaranteed money than Buster Posey’s eight-year, $159MM extension with the Giants, which is the second-biggest deal ever given to a catcher.

The largest catcher contract in history?  That agreement came exactly ten years ago today, with the Twins making the official announcement a day later.  Minnesota had inked Joe Mauer, its star player and local hero, to an eight-year, $184MM extension that covered the 2011-18 season.  Not only was it was the largest deal ever signed by a catcher, but it was the fourth-largest contract in baseball history as of March 2010 — Mauer’s payday was topped only by Alex Rodriguez’s two mega-contracts with the Rangers and Yankees, and Derek Jeter’s ten-year, $189MM extension with New York.

Could Realmuto and his representatives try to top Mauer’s contract?  Even before the coronavirus pandemic added an extra layer of uncertainty over baseball and the world at large, it didn’t seem overly likely, though Realmuto’s camp had some interest in topping Mauer’s $23MM average annual value.  Like Mauer at the time of his extension, Realmuto is just a season away from free agency, but Realmuto recently turned 29 years old, while Mauer was only entering his age-27 season at time of his deal.

Plus, there’s also the fact that the Phillies would naturally be gunshy about signing a catcher to that large a contract given how things played out in Minnesota.  Unfortunately for both Mauer and the Twins, the fairytale story of the St. Paul native staying with his hometown team and leading them to a World Series title didn’t come to pass, as 2011-18 was a lean period the franchise.  After reaching the postseason six times between 2002-10, the Twins only had one playoff appearance and two winning seasons total over the course of Mauer’s extension.

That period also saw Mauer’s production decline, though some dropoff was inevitable given the high level of Mauer’s first seven MLB seasons.  From 2004-10, only six players topped Mauer’s 34.2 fWAR, as he developed into one of baseball’s best all-around players.  Those seven years saw Mauer hit .327/.407/.481 with 81 home runs over 3578 PA, while amassing a resume that includes four All-Star appearances, four Silver Slugger Awards, three Gold Gloves, three AL batting titles, and four top-eight finishes in AL MVP voting.

Mauer’s best season came directly before his extension, as he was named AL MVP after hitting .365/.444/.587 (leading the American League in all three categories) with 28 homers over 606 plate appearances.  As per Fangraphs, Mauer’s 2009 was tied for the fifth-best season ever for a catcher in terms of fWAR, with 8.4.

These numbers add context to the extension and perhaps serve as a bit of a reminder — Joe Mauer was an awesome player in his prime.  Just about any big-market team in the game would have happily given Mauer eight years and $184MM given the opportunity to extend him, and the fact that a smaller market club like the Twins also felt comfortable in taking the plunge speaks to Mauer’s value at the time.

Of course, the Twins faced unique pressure to retain Mauer given his roots, as the idea of a literal homegrown superstar leaving for another franchise would have been a particularly tough blow for Minnesota.  It should be noted that the Twins’ extension with Mauer was met with near-unanimous praise from both their own fans and the baseball world in general, with many comparing Mauer to the likes of Tony Gwynn, George Brett, or Cal Ripken Jr. as a one-team star who would define a franchise for a generation.  ESPN.com’s Buster Olney described the extension as “going to be viewed as a strong development for Major League Baseball, at a time when there are growing concerns about the disparity between teams like the Yankees and Red Sox, and teams that generate less revenue.”

A decade after the fact, that disparity certainly remains despite the large amount of new revenue (from TV contracts and online media) coming into the sport, as it still stands out as notable when a non-major market franchise makes a particularly big splurge to sign a free agent, acquire a big contract in a trade, or ink one of its own stars to an extension.  In the latter case, teams have become more and more proactive about extending their players earlier in their careers, well before they get even a year away from free agency as Mauer did.

From 2011-18, Mauer still provided above-average (113 wRC+, 114 OPS+) production by hitting .290/.372/.405 over 4382 plate appearances.  The problem was, however, that this production was less impressive coming from a first baseman than it would have been from a catcher.  Minnesota shifted Mauer out from behind the plate after the 2013 season due to a number of concussions and knee problems, and Mauer never played catcher again until his very last game, when he caught a single pitch in the ninth inning before being substituted out.

Mauer’s contract made him a particular target for criticism during the Twins’ struggles in the 10’s, which was an unfair burden given that Minnesota’s issues had much more to do with a number of trades and signings during the decade that provided far less return than the Mauer extension.  It’s easy to say in hindsight that the Twins erred in keeping Mauer, though that also makes the assumption that the club would have spent that extra $23MM per season on more canny roster upgrades….or that the Twins would have even stretched their payroll to that extent whatsoever.

Ten years later, the Mauer extension is perhaps best seen as a defensible investment that didn’t quite pan out.  Given the perfect storm of age, production, and added hometown value that went into the contract, it may yet be a while before another catcher tops it, with Realmuto’s potential new deal with Philadelphia standing as the closest challenger in years.

Rumor Retrospection: The (Would-Be) Albert Pujols/Ryan Howard Trade Of 2010

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It was exactly a decade ago today that ESPN.com’s Buster Olney dropped a bombshell on the baseball world, reporting that the Phillies had held some internal discussions within their front office about the possibility of a blockbuster deal of first basemen — Phils slugger Ryan Howard to the Cardinals for Albert Pujols.  It would have been a one-for-one trade, with both players switching uniforms with two years remaining on their current contracts.

As Olney observed in his report, the concept might well have been just an idea floated within Philadelphia’s front office, rather than an actual proposal made to the Cards.  Phillies GM Ruben Amaro Jr. went a step further when asked to comment on the rumor, calling it “Lies.  That’s a lie. I don’t know who you’re talking to, but that’s a lie.”  (Olney defended his reporting two days later, calling it “confirmed information” and he knew “exactly who said what to whom, and how sturdy the intent was.”)

It was an eyebrow-raising trade rumor at the time, and though this particular swap apparently didn’t come close to being a reality, the concept of a straight-up superstar-for-superstar deal is still fascinating ten years later since such deals are so rare.  And, in this particular instance, we can judge with a decade of hindsight how a Pujols-for-Howard trade might have worked out for both the Phillies and the Cardinals.

For St. Louis, the impact is simple — they might not have won the 2011 World Series without Pujols.  2011 marked what was, incredibly, the least-impressive of Pujols’ 11 MLB seasons, as he “only” hit .299/.366/.541 with 37 home runs over 651 PA.  This performance was just the warmup for an epic postseason, as Pujols posted a 1.155 OPS over 82 PA during the Cardinals’ 18 playoff games.  Pujols’ efforts included a three-homer night in Game 3 of the World Series, putting him alongside Babe Ruth and Reggie Jackson as the only men (Pablo Sandoval joined the club in 2012) to ever hit three home runs in a Series game.

Could the Cardinals have won a title with Howard in Pujols’ place?  It’s possible, as while Howard wasn’t quite as productive as Pujols during the 2011 regular season, Howard still hit .276/.353/.505 and 31 homers.  Who’s to say how those numbers might have differed in a new ballpark and a new environment as a Cardinal rather than as a Phillie; Howard, a St. Louis native, might have thrived with his hometown team, or perhaps struggled under the added pressure.

What likely doesn’t happen in this what-if scenario, however, is the nasty injury Howard suffered in his (and the Phillies’) last at-bat of the 2011 season.  Making the final out of the 2011 NLDS, Howard tore his Achilles tendon leaving the batters’ box to run out a grounder, and he didn’t return to action until July 6, 2012.  It ended up being a career-altering injury for Howard, as while he was already showing a tiny bit of decline from his prime years and any sort of dropoff for a power hitter isn’t uncommon as he enters his 30’s, the before-and-after of Howard’s Achilles injury is jarring.  From 2012-16, Howard hit only .226/.292/.427 over 2122 PA.

The Phillies lost that 2011 NLDS to, ironically, the Cardinals.  It was the second straight year the Phillies had fallen short in the playoffs after a dominant regular season, and it ultimately proved to be the end of that great era of Philadelphia baseball.  In the eight years since, the Phillies have yet to enjoy another winning season, only managing an even .500 record on two occasions (2012, 2019).  While Howard was a big part of the Phillies’ success in 2010 and 2011, replacing him with Pujols’ next-level production might well have been the difference in a World Series victory in either 2010, 2011, or both seasons.

The other major side effect of this trade is what happens after the 2012 season.  A little over a month after Olney’s report, the Phillies signed Howard to a five-year, $125MM extension covering the 2012-16 seasons.  Since Howard was already 30 years old at the time of the extension and under contract for two more years, there was a pretty immediate and negative reaction to the Phillies’ decision, and while the Achilles injury wasn’t foreseen, the deal indeed ended up being a bust for the Phils.

That said, does Howard still ink an extension if he ends up with St. Louis in this alternate reality?  As Olney noted, the Cardinals weren’t making progress with Pujols on an extension, so they could have had interest in Howard as a potential long-term replacement.  The difference, however, could’ve been that the Cards might have waited at least a season before locking Howard up.  Looking back at past extensions for such Cardinals notables as Yadier Molina, Adam Wainwright, or Paul Goldschmidt, the team has tended to wait until just before the pending free agent’s final season under contract to finalize a new deal.  A Cardinals/Howard extension could been potentially lesser in both years and dollars, if Howard has performed for the Cards in 2010 as he did in the real world (.276/.353/.505 with 31 home runs) for Philadelphia.  While still strong numbers, they nonetheless represented a step back from the 50 homers Howard averaged every season from 2006-09, while also batting .278/.379/.589.

As for Pujols, he did depart St. Louis after that 2011 World Series title, signing a ten-year, $240MM deal with the Angels that still has two seasons remaining.  While the Phillies were willing to splurge on Howard, extending Pujols would’ve cost twice the years and almost twice the money as Howard’s extension.  Maybe the Phils (perhaps flush off Pujols leading them to a championship or two) would have decided that Pujols was worth the extra investment and signed him to a similar extension.  Assuming the Pujols in this multiverse declined at the same pace as our universe’s Pujols did with the Angels, such a deal could have left the Phillies with an even bigger contractual albatross on their hands….especially if the Pujols-led 2010 Phils or 2011 Phils hadn’t won a World Series, leaving the team without even a “flags fly forever” silver lining.

Another route is that the Phils work out a more creative extension with Pujols, perhaps overwriting the terms of his 2010-11 salaries to give him more money sooner and less money on the back end in his decline years.  Or, in what might have been ultimately the best-case scenario for Philadelphia, the team could have just let Pujols depart for free agency after the 2011 season.  That would have left room in the Phils’ budget and a hole at first base, which could have put the team in the market for another of that offseason’s top free agent first basemen — Prince Fielder.

Needless to say, such a major trade would’ve greatly altered the last decade of Major League Baseball, and likely swung at least one World Series result.  Given how the last ten years played out for the Phillies, maybe there’s someone from that club’s front office who, if this trade proposal indeed never got past the internal discussion phase, wishes they’d picked up the phone to at least give the Cards a call.

Transaction Retrospection: The Charlie Blackmon Extension

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Throughout the Rockies’ franchise history, the team hasn’t been shy about extending key members of the roster.  Colorado’s biggest extension yet could be in the offing, as the Rockies continue to talk with All-Star third baseman Nolan Arenado about a long-term deal that would keep Arenado away from free agency next winter.

If such a contract is worked out, it would easily be the most expensive deal in Rockies’ history, not to mention one of the pricier deals in Major League history.  It would also be the second major extension completed by Jeff Bridich in his time as Colorado’s general manager, coming on the heels of the club’s five-year extension with Charlie Blackmon last spring.  That deal is worth revisiting now, given what we’ve seen about the free agent outfield market (or, really, just the free agent market in general) after a second consecutive slow offseason of signing activity.

Blackmon was 31 at the time of the extension (he turned 32 last July 1), and, like Arenado is now, also a year away from reaching free agency.  Blackmon had posted solid numbers as a part-time player and then as a regular with Colorado in 2013-15, though he stood a big step forward to hit .327/.390/.578 with 66 homers over 1366 plate appearances in 2016-17.  That performance saw Blackmon earn a Silver Slugger Award in both seasons, as well as a fifth-place finish in NL MVP voting in 2017.

With the Rockies coming off a postseason appearance in 2017, the team moved to lock up a top performer, agreeing to an extension that guarantees Blackmon at least $94MM from 2019-23.  Blackmon earns $21MM in each of the next three seasons, and then has a player option for another $21MM season in 2022.  He then has another player option year for 2023 worth $10MM in guaranteed money, though another $8MM is available via escalators based plate-appearance thresholds that seem rather readily achievable, or on MVP finishes.  (The deal also technically adjusted Blackmon’s previously agreed-upon $14MM arbitration salary for 2018, turning $2MM of that figure into a signing bonus.)  All told, the extension could max out at $102MM in new money for Blackmon once all is said and done.

Even sticking to the guaranteed $94MM figure, however, Blackmon’s contract already looks like an outlier in the wake of how baseball’s free agent marketplace has evolved over the last two winters.  Manny Machado and Patrick Corbin are the only 2018-19 free agents who earned more than $94MM in guaranteed money this winter.  Bryce Harper will be the third name on this list once he eventually signs, and it’s doubtful that Dallas Keuchel will meet even MLBTR’s four-year/$82MM projected contract, let alone a $94MM deal.

Blackmon’s production also took a bit of a step back in 2018, as he hit .291/.358/.502 with 29 homers over 696 plate appearances.  Still strong numbers, to be sure, though more in the vein of a solidly above-average hitter (116 wRC+, 115 OPS+) than his more elite production (137 wRC+, 136 OPS+) in 2016-17.  On the defensive side, Blackmon had been a below-average but playable center fielder throughout his career, though his glovework fell off (-28 Defensive Runs Saved, -12.6 UZR.150) to such an extent in 2018 that the Rockies will now deploy him as a right fielder this season.

Had Blackmon been a free agent this winter, his most natural comp was another center fielder, A.J. Pollock.  The newly-signed member of the Dodgers outfield lacks Blackmon’s durability and longer track record of production, but Pollock is also 17 months younger, a more stable defender, and more of a sure thing to produce in a new ballpark (Blackmon has a career .970 OPS at Coors Field, and only a .745 OPS on the road).  Pollock landed a five-year deal from the Dodgers worth $60MM in guaranteed money, so even if some teams felt that Blackmon was the better free agent bet, the gap between the two players surely wouldn’t have been $34MM.

With all this in mind, it’s fair to say that Blackmon and his representatives at ACES did a good job in landing that extension last spring.  As a soon-to-be 33-year-old headed for corner outfield duty, as hard to imagine Blackmon would’ve found five years and $94MM in free agency if he had tested the market this winter.

A win for Blackmon, however, doesn’t at all mean that the deal was a “loss” for the Rockies.  As noted, Blackmon was still a very productive hitter in 2019 — drastic home/road splits aren’t as big an issue when you’re the team that plays at Coors Field, naturally.  Blackmon also wouldn’t be the first player to improve at the plate after shifting to a less-demanding defensive position, so getting out of center field could help Blackmon’s bat as well as simply drastically elevating his defensive value.

Could Colorado have re-signed Blackmon to a lesser deal as a free agent had they not extended him a year early?  Potentially, though such a “what-if” scenario is easy to create with 20/20 hindsight (plus, you never know if another team might’ve been particularly keen on signing Blackmon).  As it worked out, the Rockies were able to retain a player they liked both on the field and in the clubhouse, even if it may have been a bit of an overpay.

Let’s also not overlook the big-picture ripple effect of the Blackmon extension as it relates to Arenado.  The third baseman now has solid proof that a Bridich-led front office is willing to pay to keep a homegrown star in the fold, and retain members of what has been a winning core group that has reached consecutive postseasons.  Money-wise, Blackmon’s long-term contract presents no real obstacle to the Rockies being able to afford Arenado, given that negotiations are already taking place and the organization is cognizant of the $200MM+ it will surely take to keep Arenado in the fold.  From a return-on-investment standpoint, Blackmon’s contract also looks like much less of a problem for the Rockies’ payroll than the lack of production they’ve received from recent free agent signings like Ian Desmond, Jake McGee, or Bryan Shaw.

It will also be interesting to see how Blackmon’s extension stands in the wider scope of future extensions for star players a season away from free agency.  We’ve already seen some notable extensions this spring, though those deals went to players (Aaron Nola, Luis Severino, Jorge Polanco, etc.) who were still arbitration-controlled for several seasons, rather than pending members of the 2019-20 free agent class.  For some of those scheduled free agents who are already in their 30’s, the thought of an extended stint in free agency and/or a lesser contract than expected have surely crossed these players’ minds in the wake of the last two offseasons.

Blackmon’s contract may represent a best-case scenario for such players if they do pursue extensions, as Blackmon and his camp were able to score at what may be the peak of the outfielder’s value and earning potential.  Of course, it takes two to tango, and it remains to be seen if teams besides the Rockies are willing to pay a premium in an extension for a player who isn’t either a true elite veteran (like a Nolan Arenado) or a younger, arbitration-controlled star who could prove to be a bargain if locked up early.  As a team wanting to both win now and to send an early signal to Arenado that they wanted to win the future, however, the Rockies felt Blackmon’s extension was clearly worth the plunge.

Transaction Retrospective: The First Aroldis Chapman Swap

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Tomorrow is the two-year anniversary of the trade that sent Aroldis Chapman from the Reds to the Yankees. While Chapman is currently ensconced as New York’s closer, just as he was in the wake of the swap, the intervening period has seen quite a few twists and turns.

Aroldis Chapman

Six years before the trade, the Reds had landed Chapman as a free agent, staking a hefty $30.25MM bet on the power pitcher from Cuba. He proved the team wise, providing 319 innings of 2.17 ERA pitching and racking up 146 saves.

Entering the 2015-16 offseason, though, it seemed clear that it was time for both sides to move on. Chapman had just one year of control remaining, after all, and the Reds were coming off of a 64-win season. While the team struggled, Chapman was his typically dominant self, and seemed positioned to draw a big return.

In early December, it seemed Chapman was destined to join Kenley Jansen to form a terrifying one-two punch in Los Angeles. Precise details of the proposed Dodgers swap were never clear, though reportedly the Reds would not have added then-top L.A. prospects Julio Urias, Corey Seager, or Jose De Leon.

Just when it seemed a deal was imminent, though, a stunning off-field development intervened, as reports emerged that Chapman had been arrested earlier in the offseason for a troubling domestic incident. With Chapman’s reputation tarnished and a possible suspension looming, the Dodgers backed away and the market dried up.

Thus it was that the Yankees stepped into the void and placed a somewhat controversial bet on the game’s most intimidating reliever. Despite already carrying a fantastic late-inning duo of Andrew Miller and Dellin Betances, the Yanks saw an opportunity to create a three-headed bullpen monster. They shipped four prospects — third baseman Eric Jagielo, second baseman Tony Renda, and right-handers Rookie Davis and Caleb Cotham — to Cincinnati to acquire Chapman.

The risk, really, was never on the field or even in the course of the investigation: Chapman was one of the surest relievers in baseball and had he received a sufficiently lengthy suspension, he’d have been eligible for another season of arbitration. Rather, the Yanks were gambling that Chapman would be valuable enough to warrant absorbing a significant public relations hit.

While he was never arrested or charged with a crime, Chapman was rightly criticized and ultimately suspended for what commissioner Rob Manfred determined to be violent actions directed toward his girlfriend. He eventually acknowledged he “should have exercised better judgment” but insisted he “did not in any way harm [his] girlfriend that evening.”

At the same time, it is hard to escape the conclusion that the Yankees benefited greatly from taking him on. After returning from a thirty-game ban, Chapman picked up right where he left off, throwing 31 1/3 innings of 2.01 ERA pitching leading into the trade deadline. With the Yanks in a less-than-promising postseason position, the organization decided to market Chapman in the summer trade market, finding interest far more robust than had existed just months earlier.

Thus it was that the Yankees ended up with a foursome of players immensely more valuable than that which it had shipped to Cincinnati. New York sold the rights to rent Chapman for the remainder of 2016 to the Cubs, who obviously saw him as the final piece needed on a World Series-caliber roster.

Infielder Gleyber Torres was the undeniable headliner; he’s now seen as one of the game’s very best prospects. Though Rashad Crawford has yet to show much since coming to New York, outfielder Billy McKinney is now fresh off of a promising season in which he restored some of his former prospect luster. And the Yanks even came away with right-hander Adam Warren, who has provided 87 2/3 productive relief innings since the swap and is still under team control via arbitration for one more season.

Then, of course, there’s the fact that Chapman ended up returning to the Bronx after his brief stint with the Cubs. In the first year of his record-setting $86MM contract, the now-29-year-old Chapman wasn’t quite as devastating as usual — his 3.22 ERA was the second-highest mark of his career, and he has never before ended a season with a lower strikeout rate than his 12.3 K/9 — but he still averaged a triple-digit heater. While there are some signs of concern, including a plummeting swinging-strike rate, Chapman generally figures to remain one of baseball’s better closers for some time.

As for the Reds? Only Davis and Jagielo remain in the organization. As for the former, there’s certainly hope he’ll be a MLB contributor. Davis did make it up to the majors in 2017, though he struggled quite a bit and was less than dominant at the highest level of the minors. Jagielo, 25, struggled in his first attempt at Triple-A in 2017 and does not rate among the organization’s top thirty prospects, per MLB.com.

It remains a major disappointment for the Reds that they were unable to fully capitalize on Chapman. While some argued that the organization was foolish not to have carried him into the 2016 season rather than accepting a discounted return, that action would have come with its own significant risks. If there’s a silver lining, perhaps it’s that the Reds have since come to realize another successful investment in a high-powered Cuban reliever. Raisel Iglesias has now established himself as one of the game’s best young closers. For the time being, at least, it seems he’s staying put as the anchor of the Cincinnati bullpen.

Photo courtesy of USA Today Sports Images.

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