The club was plenty familiar with Cortes when they signed him to the deal, as it was actually the lefty’s third stint in the Bronx. First drafted by the club in the 36th-round of the 2013 draft, Cortes was plucked from the club in the 2017 Rule 5 draft by the Orioles, but was returned just a few months later. He then threw 66 2/3 innings of work for the Yankees during his rookie season in 2019, though he struggled to a 5.67 ERA and found himself traded to the Mariners that November. Cortes made just five appearances in Seattle before electing minor league free agency and returning to the Yankees prior to the 2021 season.

The lefty’s return to the Bronx wouldn’t get underway in earnest until deep into May, when he was added to the club’s roster as a multi-inning relief option out of the bullpen. Cortes’s first appearance of the year came on May 30 against the Tigers, and he pitched somewhat unevenly with two runs (one earned) allowed in 3 2/3 innings of work that saw him strikeout three, give up three hits and walk four. Throughout the month of June, however, Cortes looked utterly dominant. He pitched to a microscopic 0.64 ERA across six appearances (14 innings) that month and struck out a whopping 42.3% of opponents.

That overpowering run of success earned Cortes a spot in the starting rotation when the calendar flipped to July, and he managed to keep a hold on that spot in the Yankees’ rotation throughout the remainder of the season. In 14 starts throughout the second half of the season, Cortes pitched to an excellent 3.07 ERA in 73 1/3 innings of work and struck out a respectable 25.4% of his opponents. His emergence helped the Yankees to weather injuries to Corey Kluber, Luis Gil, and Domingo Germán that tested their starting depth throughout the season. While Cortes didn’t pitch in the postseason that year as the Yankees fell to the Red Sox in the AL Wild Card game, he entered 2022 with a firm grip on a role in the starting rotation.

It turned out to be a career year for the left-hander. Cortes was among the very best pitchers in the sport in 2022, earning his first (and to this point, only) All-Star appearance and finishing within the top 10 of AL Cy Young award voting that year. While his 158 1/3 innings of work weren’t enough to qualify for the ERA title, he made a respectable 28 starts and his 2.44 ERA was the seventh-lowest in the majors among hurlers with at least 150 innings of work and left him sandwiched between Shohei Ohtani and Max Fried on that year’s leaderboard. His 26.5% strikeout rate, 3.13 FIP, and 3.7 fWAR all ranked in the top 20 among that group as well. The season to remember saw Cortes go on to make three key postseason starts for the Yankees that October. He cruised through two starts against the Guardians with a 2.70 ERA in ten innings but was ultimately on the mound for the Yankees’ final game of the season, when the Astros completed their sweep of the Bombers in Game 4 of the ALCS.

Following Cortes’s career year in 2022, the lefty saw his production take a bit of a downturn. 2023 was something of a lost season for Cortes, as he made just 12 starts due to a pair of rotator cuff strains and struggled to a below-average 4.97 ERA when he was healthy enough to take the mound. 2024 was a step in the right direction for the lefty as he was healthy for the majority of the year, but his results paled in comparison to what they had been in the first two years of his return to Yankee Stadium. In 174 1/3 innings of work for the Yankees last year, he pitched to a 3.77 ERA (109 ERA+) with a 3.84 FIP but struggled in the second half with a 4.41 ERA over his final 12 appearances.

Still, that’s solid mid-to-back of the rotation production overall and it was a worrying hit to the club’s depth when a late-season flexor strain seemingly endangered Cortes’s postseason in late September. The lefty made it back to the mound in time for the club’s World Series appearance against the Yankees, although some fans might wish he hadn’t done so after he surrendered a walk-off grand slam to Freddie Freeman in the tenth inning of Game 1. Cortes went on to throw 1 2/3 scoreless relief innings in Game 3, but had little impact during the rest of the series as the Yankees dropped the series to the Dodgers in five games.

New York traded Cortes for a second time last month when they packaged him with infield prospect Caleb Durbin and cash considerations to acquire star Brewers closer Devin Williams. At least for the time being, that trade has brought Cortes’s lengthy Yankees story to a close. With Cortes entering his age-30 season and just one year away from free agency, it’s anyone’s guess if he’ll find himself back in the Bronx at some point before his career comes to a close, but he leaves New York as one of the club’s most valuable signings in recent years.

Over the last four seasons, the lefty has pitched to a 3.33 ERA in 489 innings of work across 93 appearances (84 starts) while punching out 25.2% of his opponents. It’s a performance that was worth 9.4 fWAR and 10.3 bWAR, and even in 2025 the decision to bring Cortes back into the fold figures to be a gift that keeps on giving now that Williams and his career 1.83 ERA will spend his final year before free agency closing out games in the Bronx. Garnering that level of production out of a mid-20s minor league signing who has a career ERA north of 6.00 is something any club would be elated about, and the outcome stands as a clear win for Brian Cashman’s front office.

The deal came as something of a surprise, as the Rays weren’t under huge financial pressure to move Snell. Despite the controversy surrounding Kevin Cash’s decision to lift Snell in Game 6 of that year’s Fall Classic, Tampa Bay could’ve held the southpaw into the following season. Snell was under contract for respective salaries of $10.5MM, $12.5MM and $16MM covering the 2021-23 campaigns.

Nevertheless, the Tampa Bay front office felt the prospect return was too strong to pass up. Patiño was viewed as one of the sport’s most talented pitching prospects despite struggling in a brief MLB debut that season. Hunt was a borderline Top 100 minor leaguer at the time. Mejía’s stock had fallen from its peak as he struggled against big league pitching, but he was only entering his age-25 season and had less than three years of MLB service. Wilcox was viewed by many evaluators as a first-round talent that year, only dropping to the third because of a lofty bonus demand.

The deal didn’t pan out at all as the Rays had envisioned. While Snell has had a volatile career, he recaptured the ace-caliber upside he’d shown in Tampa Bay. After turning in a 4.20 ERA over 27 starts during his first year with the Friars, he rebounded to post a 3.38 mark in 2022. The cumulative 3.79 ERA he managed across 256 2/3 innings was solid, although it didn’t hint at the Cy Young level he’d reach in 2023.

Snell didn’t start the ’23 campaign well. He owned a 5.48 ERA with a strikeout rate just under 24% through the first month. After a slight uptick in strikeouts and a 3.82 mark in May, Snell kicked off a four-month stretch as the most dominant pitcher on the planet. From June 1 on, he struck out 35% of batters faced and allowed 1.23 earned runs per nine. His 1.54 ERA after the All-Star Break is the 12th-lowest second half rate since 2000 (minimum 75 innings).

The dominating finish led Snell to cruise to a second career Cy Young. He was a near-unanimous choice as the NL’s top pitcher after posting an MLB-best 2.25 ERA through 180 innings. Snell hit free agency and seems unlikely to return to a San Diego organization that has cut spending. Assuming he signs elsewhere in the coming weeks, he concludes his time as a Padre with a 3.15 ERA while striking out 31.5% of opponents in 436 2/3 frames.

As a team, San Diego didn’t have the kind of success they envisioned. They reached the postseason just once in the last three years. A second-half collapse cost them a playoff berth in 2021. They rebounded with a trip to the NLCS in ’22 but finished 82-80 last season. A strong final couple weeks ostensibly brought them within a couple games of a playoff spot, but the 2023 club was more or less finished by the end of August.

One can debate whether the Friars should’ve more aggressively marketed Snell, Juan Soto and Josh Hader at the deadline. A fringe contender at the time, they elected to add around the margins rather than move their top impending free agents or Soto (whose arbitration price tag they knew was rising). As a team that exceeded the luxury tax threshold, they’ll only receive picks after the fourth round as compensation for losing Snell and Hader, each of whom rejected a qualifying offer.

San Diego’s subsequent decisions don’t negate how well they fared in the Snell trade, however. That turned out to be one of the more lopsided deals of the past few seasons. No one in the return found much success in Tampa Bay. Three of the four are out of the organization entirely.

Patiño saw MLB action in each season from 2021-23. He logged 101 1/3 innings as a Ray, turning in a 5.24 ERA. Patiño’s control hasn’t developed as expected and he has struggled with home runs throughout his MLB tenure. The Rays moved on at the deadline, sending him to the White Sox for cash. He ended up back in San Diego last week; the Friars claimed him when Chicago put him on waivers. He’s out of options, so he’ll either need to open the season on the MLB roster or be made available to other teams yet again.

Neither of the other prospects involved have reached the majors. Hunt has slowly climbed the minor league ladder, hitting at a roughly league average level at each stop. The Rays didn’t want to carry him on the 40-man roster, yet Hunt was eligible for minor league free agency after this season. Tampa Bay dealt him to the Mariners (who did add him to the 40-man) for 2022 eighth-round pick Tatem Levins last month. Wilcox remains in the organization but underwent Tommy John surgery late in the ’21 season. He returned to post a 5.23 ERA in 25 starts at Double-A this year. He went unselected in the Rule 5 draft a few weeks ago.

Mejía, arguably the fourth piece of the return at the time, had the most success for Tampa Bay. The switch-hitting catcher had a .260/.322/.414 batting line in 84 games in 2021. His offense cratered over the last two years, though, as he hit .237/.262/.387 in 459 plate appearances over that stretch. The Rays designated him for assignment in August. He reached free agency at year’s end and signed a minor league deal with the Angels last week.

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On this date four years ago, the Rays and Rangers lined up a deal that was more an interesting swap of young players than a pivotal deadline move. It was a one-for-one that sent reliever Pete Fairbanks to Tampa Bay and second base prospect Nick Solak to Arlington.

Fairbanks had some MLB experience, but neither player was an established big leaguer at the time of the trade. The right-hander had pitched in eight games for Texas. He averaged over 97 MPH on his heater but had allowed 10 runs in 8 2/3 frames. Solak hadn’t yet gotten to the majors; he was hitting .266/.353/.485 with 17 homers in Triple-A at the time of the deal.

Despite being the player without MLB experience, Solak was probably the more well-known of the two at the time. He’d been a 2nd-round selection of the Yankees a few years before. Solak was already involved in one notable trade, going to Tampa Bay in the 2018 three-team deal that sent Brandon Drury from Arizona to the Bronx.

Prospect evaluators consistently raised questions about Solak’s defensive acumen at second base. There was less trepidation about his offensive upside, though. He’d been an accomplished minor league hitter and was on the doorstep of the majors. Fairbanks had high-octane stuff but spotty control and had twice undergone Tommy John surgery as a minor leaguer, a big reason he was still unestablished by his age-25 campaign.

The initial returns looked promising for Texas. Solak debuted a month later and hit .292/.393/.491 over his first 33 MLB contests. He’d get the Opening Day nod in left field the next season. Fairbanks pitched 13 times for the Rays, allowing 10 runs across 12 1/3 frames.

Beginning in 2020, the deal swung definitively in Tampa Bay’s favor. Fairbanks was excellent in the shortened season, working to a 2.70 ERA while fanning a third of opponents in 27 regular season outings. He pitched nine times during the Rays’ run to the pennant, securing three saves and holds apiece in the playoffs. Fairbanks logged a career-high 42 2/3 innings the next year, working to a 3.59 ERA with 14 holds and a 29.7% strikeout rate.

Solak, on the other hand, never built off that strong debut. He hit .246/.317/.354 in a little more than 800 MLB plate appearances from 2020-22. Concerns about his defense were founded and pushed him more frequently to left field. Texas parted with him at the start of last offseason, trading him to the Reds for cash. Solak has consistently hit well in the upper minors but has bounced around via waivers and small trades since the Rangers moved on. He’s currently in Triple-A with the Tigers.

Fairbanks’ durability concerns have presented themselves over the past two years. He lost the first half of last season to a lat strain. He’s battled Raynaud’s syndrome, a condition that can lead to a cold numbness in the fingers, on a couple occasions. Hip inflammation cost him a few weeks earlier this year.

Still, the Rays have to be pleased with the work they’ve gotten out of Fairbanks. He’s one of their top relievers, owner of a 2.78 ERA in 123 regular season innings since the trade. He has allowed only six runs in 15 postseason frames over three seasons. The Rays signed him to a three-year deal in January, guaranteeing him $12MM to buy out his final three arbitration years and secure a 2026 club option.

No one would argue the Fairbanks trade was as impactful as acquiring the likes of Randy Arozarena or Isaac Paredes. It proved an adept pickup, though. Adding an effective late-inning arm for a young hitter who fell a bit short of expectations has paid off. The front office and coaching staff surely hope Fairbanks will continue to play a key role in postseason runs over the years to come.

That contract guaranteed the Venezuelan-born righty $43MM over five seasons. Márquez had between two and three years of service at the time. The deal bought out all four seasons of arbitration eligibility — he’d qualified for early arbitration as a Super Two player — and at least one free agent year. It also contained a club option for a sixth season, potentially pushing Colorado’s window of control out by two years.

It remains the second-largest extension for an arbitration-eligible pitcher within that service window, trailing only the $50MM deal Blake Snell had signed with Tampa Bay the month prior. Márquez was coming off the best season of his career, throwing 196 innings of 3.77 ERA ball with a 28.2% strikeout rate to help the Rox to a playoff berth.

The results over the past few seasons have been mixed. Márquez’s ERA backed up to 4.76 in 2019. His peripherals remained solid, although his strikeout rate dropped by almost four percentage points. Márquez rebounded with a 3.75 ERA over 13 starts during the shortened season, a strong mark for a pitcher who spends half his time at Coors Field. He earned his first All-Star nod in 2021, as he carried an excellent 3.36 ERA through that year’s first half. Opposing hitters teed off towards the end of that season, though, tagging him for more than six earned runs per nine innings after the All-Star Break.

Those struggles lingered into the following season. Márquez’s 2022 campaign was arguably the worst of his career. While he stayed healthy and soaked up 181 2/3 frames in 31 outings, his 4.95 ERA was his highest mark (excluding a six-outing debut in 2016). His 20% strikeout percentage was a hair below the league average. Márquez hasn’t missed bats as frequently as he did back in 2018 even though his average fastball velocity has held steady in the 95-96 MPH range. His slider and curveball speeds have gone up a couple ticks over the years but have lost some depth, contributing to the dip in whiffs.

Including his first two starts this year, Márquez owns a cumulative 4.58 ERA in 106 starts since the beginning of the 2019 season. He’s been durable and easily leads the team in innings, soaking up 628 2/3 frames over that stretch. Márquez has punched out 22% of opponents, kept his walks to a 7.1% rate and induced grounders at a 49.5% clip. That’s slightly above-average production after accounting for his home park, with a 4.08 SIERA painting him as a capable #3 type starter. Yet while he flashed top-of-the-rotation numbers at times, his past year and a half have been below his early-career standards.

The Rockies have gotten solid value out the Márquez extension and it’s a deal they’d likely sign again in hindsight. The organization has signed a few other arbitration-eligible players to extensions with mixed results. Ryan McMahon is signed through 2027, while the club locked up Kyle Freeland and Antonio Senzatela through 2026. The McMahon deal ($70MM over six years) looks like solid value. The club didn’t get much from Senzatela or Freeland last year, the first seasons of their respective contracts. A three-year, $14.5MM deal for backstop Elias Díaz didn’t go well in year one.

Colorado hasn’t found any team success over the past four seasons. They’ve finished either fourth or fifth in the NL West every year, and they’re generally expected to do the same in 2023. They’re potentially facing an inflection point with Márquez, as this is the final guaranteed season of his deal. The Rox hold the aforementioned club option next year, which is valued at $16MM and comes with a $2.5MM buyout. That still looks like decent value considering his career body of work. Jameson Taillon and Taijuan Walker, for instance, each secured $17-18MM annually over four years as free agents last offseason. If Márquez repeats his 2022 numbers, however, it could be a more borderline call for the Colorado front office.

The Rox might also have to again grapple with trade questions this summer. Colorado has made clear they wouldn’t listen on Márquez near the deadline in recent seasons. That could well again be the case considering the organization’s longstanding opposition to a retool or complete teardown. As the extension gets closer to its conclusion, that decision could become tougher for general manager Bill Schmidt and his front office.

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At the time, Darvish seemed like a much-needed injection of frontline rotation talent for the Cubs. After falling to the Dodgers in the NLCS in their title defense season, swiping Darvish from the Dodgers had the potential to swing a potential rematch in seasons to come.

That rematch wouldn’t come to pass, however. Darvish would make just nine starts for the Cubs in the 2018 season. Though they won 95 games, Joe Maddon’s club stumbled into a wild card spot before losing the wild card game to the Rockies on a Tony Wolters RBI single in the 13th inning.

The timing was never quite right for Darvish and the Cubs. He was better in his second season in Chicago, but not good enough to change the fortunes of their fledgling contender. Darvish finished second for the NL Cy Young during the pandemic-shortened 2020 season, but they fell in the first round of the playoffs to the Marlins.

Though Darvish was incredible during that 2020 season (2.01 ERA/2.23 FIP over 76 innings), the Cubs chose to sell high on their one-time free agent prize, sending him to the Padres for a quartet of teenagers. The Cubs were largely criticized at the time of the deal, though the full impact of the move won’t be known for many years yet. There’s no doubt that Chicago needed an injection of youth for a system that had largely stagnated during their years of contention. Further, in terms of maximizing their assets, Darvish was their most valuable trade piece at the time.

And though Darvish’s arsenal is robust, and he’s among the strikeout leaders on a per batter basis year-by-year, his bottom line run prevention numbers don’t necessarily paint him as one of the best pitchers in the league.

He was certainly a touch disappointing in his first season with the Padres, posting just 1.4 rWAR/2.9 fWAR despite making 30 starts and tossing 166 1/3 innings. The 34-year-old wasn’t bad in 2021, but with a 4.22 ERA/3.90 FIP, Darvish looks more like a solid mid-rotation arm than a true frontline ace, even with an impressive 29.2 percent strikeout rate and 6.5 percent walk rate.

The fact is, outside of his tremendous 2020 season, Darvish has been closer to this 2021 self for most of his Major League career – at least since missing the 2015 season. Still, that makes for a valuable rotation arm that ought to play a valuable role for the Padres over the next two seasons, even in his age-35 and age-36 seasons.

At the same time, it’s hard to fault the Cubs now for selling when they did. MLBTR readers did not like the deal, with the most popular grades being a C and D at the time. But in retrospect, the Cubs were clearly more than a Darvish away from competing last season.

On the whole, even though they traded him halfway through the deal, the Cubs probably still feel pretty good about their decision to sign Darvish. On the field, he gave them 294 2/3 innings over three seasons with a 3.60 ERA/3.77 FIP, totaling 5.8 fWAR. Those aggregate numbers are solid, though they came in the shape of one subpar season, one stellar season, and one middle-of-the-road year in 2019.

Taking a more holistic approach, you can give Darvish credit for also netting the organization four prospects who may still provide a boost to Cubs teams down the road. As of right now, Fangraphs has the four prospects the Cubs got for Darvish ranked as their #3, #5, #37, and #48 ranked prospects in their system. Will those four prospects end up being more valuable than the final three years of Darvish’s free agent deal? That’s a question for a future date. In terms of the free agent deal that was signed four years ago today, the move didn’t turn out exactly the way the Cubs perhaps wanted, but they should count it as a win nonetheless.

• 2021: The Blue Jays officially announced their one-year, $18MM deal with Marcus Semien, as the two sides agreed to the contract a few days prior.  In the aftermath of a disappointing 2020 season with the A’s, Semien opted for the one-year pact with Toronto in order to rebuild his free agent value with a better performance in 2021.  This plan worked to perfection, as Semien finished third in AL MVP voting after hitting .265/.334/.538 with 45 home runs (a new single-season record for a second baseman).  Semien then cashed in during his most recent trip to the open market, signing a seven-year, $175MM contract with the Rangers signed prior to the lockout.
• 2021: In another notable move completed one year ago, the Athletics acquired Cole Irvin from the Phillies in exchange for cash considerations.  Irvin hadn’t done much over 45 1/3 career innings with Philadelphia, but the southpaw emerged as a valuable member of Oakland’s rotation last year, posting a 4.24 ERA over 178 1/3 innings.  While the Statcast metrics weren’t kind to Irvin and questions remain as to whether or not he can stick as a reliable starting pitcher, and yet for the cost of just a minor cash outlay, the trade was already a win for the A’s.  It is possible Irvin wouldn’t have broken out without a change of scenery, and yet the deal doesn’t look great in hindsight for the Phillies, especially considering the Phils spent much of the season looking for consistency at the back of their rotation.
• 2016: Jean Segura was traded for the second of four times in his career, as the Diamondbacks acquired Segura and right-hander Tyler Wagner from the Brewers for a package of Chase Anderson, Isan Diaz, Aaron Hill, and $5.5MM to cover part of Hill’s remaining salary.  Segura’s lone season in Arizona was the best of his career (.319/.368/.499 with 20 homers as part of a 5.0 fWAR campaign), but it wasn’t enough to keep the D’Backs from a 93-loss season.  With Mike Hazen taking over as Arizona’s GM in the aftermath of that rough season, Segura found himself on the move again in November 2016, traded to the Mariners in another notable swap that brought Ketel Marte to the desert.  From Milwaukee’s perspective, their Segura trade ended up being a nice win.  Anderson became a solid member of the rotation for four seasons, while Diaz was part of the prospect package the Brewers sent to the Marlins to land Christian Yelich.
• 2006: Hey, remember when Mike Piazza played for the Padres?  The Hall-of-Famer spent only one season in a Friars uniform, but it was a memorable one, sparked when Piazza signed a one-year, $2MM deal (with an $8MM mutual option for 2007).  Getting the bulk of playing time as San Diego’s starting catcher, Piazza still plenty left in the tank at age 37, hitting .283/.342/.501 with 22 home runs over 439 PA.  Piazza’s big year helped the Padres win the NL West, but the team declined their end of the mutual option after the season.
• 1954: Bobby Thomson’s legendary home run helped THE GIANTS WIN THE PENNANT in 1951, but it can be argued that trading Thomson helped the Giants win the World Series in 1954.  On this day 68 years ago, the then-New York Giants picked up left-handers Johnny Antonelli and Don Liddle, backup catcher Ebba St. Claire, infielder Billy Klaus and $50K in cash from the then-Milwaukee Braves in exchange for Thomson and catcher Sam Calderone.  Antonelli became a fixture of the Giants rotation for the next seven seasons, reaching six All-Star games and posting a league-best 2.30 ERA in 1954.  Liddle was also a solid arm for New York in 1954, and might be best remembered for allowing the long Vic Wertz fly ball that required Willie Mays to make “The Catch” in Game 1 of the 1954 World Series.  Brought into the game specifically to face Wertz, Liddle was removed after facing his one batter — according to legend, Liddle then wisecracked “well, I got my man” in mock-bragging fashion after leaving the game.
• 1923: It’s not quite the most famous example of the Red Sox trading a future Hall-of-Famer to the Yankees, since it’s not like Boston fans bemoaned “The Curse Of Herb Pennock.”  Still, the Yankees never won a World Series before Pennock came to the Bronx, dealt from Boston for $50K and three players who were all gone from the Sox roster by 1925.  Pennock was already a 10-year veteran with a solid career behind him at the time of the trade, but after a couple of relative down years in 1921 and 1922, the Sox were ready to move on.  Pennock went on to pitch 11 seasons with the Yankees, posting a 3.54 ERA over 2203 1/3 innings and helping New York win four Series championships.  The southpaw was at his best in October, with a 1.95 ERA over 55 1/3 career innings in World Series play.

As part of that January 21, 2019 agreement, the Reds landed Sonny Gray. Cincinnati agreed to take on the right-hander’s $7.5MM salary for that season and promised him an additional $30.5MM through 2022. (The deal also included a $12.5MM club option for 2023). The Reds also landed left-handed pitching prospect Reiver Sanmartín from New York. In exchange, they sent infielder Shed Long Jr. to Seattle, who flipped their recent second-round draftee, Josh Stowers, to the Yankees.

Gray, an All-Star and AL Cy Young award finalist in 2015, was the obvious headliner of the deal. After a generally strong run in Oakland, he was sent to the Yankees at the 2017 trade deadline. Yet Gray didn’t fare as well during his year-plus in the Bronx, posting a mediocre 4.51 ERA/4.40 FIP across 195 2/3 innings. He dealt with particular struggles in the hitter-friendly confines of Yankee Stadium, managing a 6.55 ERA in home contests during his time in pinstripes.

The Reds identified Gray as a target as they neared the end of a rebuild that had landed them in the basement in the NL Central for four straight seasons. They were rewarded for that decision, as Gray immediately turned things around in his new environs. He twirled 175 1/3 frames with a 2.87 ERA during his first season with the Reds, earning his second All-Star nod and some down ballot Cy Young votes in the process. Both FanGraphs and Baseball Reference pegged Gray as the most valuable player on the team that year by Wins Above Replacement.

Gray’s excellent debut season wasn’t enough to get the Reds to the postseason, but Cincinnati did qualify for an expanded playoff the next year. His 56 innings of 3.70 ERA ball in the shortened season weren’t quite as impressive as his first-year numbers, but it was still solidly above-average output that contributed to a decent 31-29 team showing. The Reds didn’t make the playoffs over a full schedule last year, but Gray had another nice showing. The 32-year-old’s 4.19 ERA marked a bit of a step back, but a 27% strikeout rate, 47.2% ground-ball percentage and 3.85 SIERA suggest he may have been adversely affected by a poor defense behind him.

Cincinnati hasn’t had the team success they’d no doubt hoped to achieve over the past three seasons. That’s not any fault of Gray’s, though. Over 366 2/3 innings with the Reds, the Vanderbilt product has posted a 3.49 ERA/3.57 FIP, holding opposing hitters to a meager .208/.292/.345 line. Buying low after his struggles with the Yankees proved a shrewd move for former president Dick Williams, general manager Nick Krall, and the rest of the Cincinnati front office.

It remains to be seen whether Gray’s tenure with the Reds is finished. He’s still controllable for two seasons under the terms of the extension he signed at the time of the trade. The organization may be looking to cut payroll after the lockout, and Gray perhaps offers the best blend of recent productivity, availability in trade and 2022 salary (around $10.167MM) of anyone on the roster.

Whether Gray winds up dealt for a third time or opens next season in Cincinnati, the deal counts as a win for the Reds in retrospect. In fact, of the three prospects involved in the trade, Sanmartín is the only one who remains with the club that acquired him. He made his first two MLB starts during the final week of last season and could be a depth starter or long reliever for Cincinnati this year.

The other two prospects — Long and Stowers — were more well-regarded than Sanmartín at the time of the trade. Neither emerged as a long-term option in their new organizations, though. Long tallied 412 plate appearances over three years with Seattle. He hit well as a rookie but struggled between 2020-21, dealing with recurring injury issues around his right shin. Outrighted off the Mariners 40-man roster at the end of last season, the 26-year-old elected minor league free agency and has yet to sign elsewhere. Long figures to get another opportunity — even if just via minors pact — and he’s young enough to have a real chance at turning things around, but he didn’t make the kind of impact in Seattle their front office no doubt hoped he would.

Stowers, meanwhile, has yet to crack the majors. He spent two years in the New York farm system, then was traded to the Rangers last April as part of the deal that sent Rougned Odor to the Bronx. The 24-year-old outfielder (25 next month) then hit .220/.311/.466 across 351 plate appearances in Double-A. Not added to the Texas 40-man roster after the season, he’ll be eligible for selection in the Rule 5 draft once the lockout wraps up. As with Long, it’s far too early to close the books on Stowers’ career, but he’ll be available to the rest of the league for little more than an active roster spot in the coming months.

The deal also netted the Yankees the Reds’ Competitive Balance pick in the upcoming draft. New York used that selection (#38 overall) to nab left-hander T.J. Sikkema from the University of Missouri. Sikkema, who missed the entire 2021 campaign due to injury, was ranked by Baseball America as the #23 prospect in the Yankees’ system midseason. Between the lost minor league season in 2020 and last year’s injury-wrecked campaign, he’s still yet to advance to full season ball. Sikkema will be eligible for next offseason’s Rule 5 draft if not added to the New York 40-man roster, making the 2022 campaign a particularly important one for his future in the organization.

Note: This article was updated to reflect that the Yankees also acquired a Competitive Balance Selection from the Reds.

It was easy to see the appeal for the White Sox in betting on Anderson long-term. He was a former first-round pick and top 100 prospect, so one could envision him as a core piece of the future. Anderson had also held his own as a 23-year-old the year prior. The young shortstop made his MLB debut in June 2016 and hit a decent .283/.306/.432 over 431 plate appearances down the stretch.

There’s also the reality that early-career extensions tend to carry ample upside with little downside for teams. With the MLB salary structure designed to underpay players early in their careers, extensions for those players often tack on extra years of team control at rates well below what the player would’ve made in free agency if they perform at a high level. Meanwhile, the figures are typically low enough the team can paper over the deal if the player busts.

Still, this contract represented something of a show of faith on the White Sox’s part. Anderson had yet to accrue a full year of MLB service, so he would’ve been controllable through 2022 regardless. His strikeout and walk rates had been well worse than the league average in 2016, so a wait-and-see approach would’ve been reasonable, particularly with the organization embarking on a rebuild. Instead, Chicago placed a bet on Anderson’s long-term development. As Jeff Todd examined for MLBTR, the guarantee set a new high-water mark at that time for a player with less than one year of major league service.

The White Sox are now in position to be handsomely rewarded for that decision. After making the playoffs in 2020, Chicago looks well-positioned to continue to contend over the next few seasons. Anderson is a central reason for that. He has hit a stellar .331/.357/.514 (133 wRC+) over the past two seasons, finishing seventh in American League MVP voting in 2020.

While he has never drawn many walks, Anderson has improved in virtually every other regard since his rookie season. He’s cut his strikeout rate in recent years while hitting for more power and reliably posting high batting averages on balls in play. Anderson will play out the next two seasons on respective guaranteed salaries of $7.25MM and $9.5MM. Barring an unexpected drop in performance or injury, the White Sox should have little hesitancy excising the 2023-24 options (valued at $12.5MM and $14MM, respectively) and keeping Anderson in Chicago for the first half of this decade.

To date, the trade is shaping up to be a rare win-win. Realmuto more than lived up to his end of the bargain. Since the start of 2019, the former third-rounder has hit an above-average .273/.333/.492, all while rating as a high-end pitch framer and throwing out an elite 42.9% of attempting basestealers. He and Yasmani Grandal are well clear of the rest of the field when looking at FanGraphs’ WAR leaders among catchers the past two seasons. The Phillies didn’t find much in the way of team success, but that’s not the fault of Realmuto, who has been one of the sport’s two most productive catchers since the trade.

Of course, the Phillies-Realmuto relationship didn’t end once he reached free agency. Philadelphia brought back the franchise backstop on a five-year contract last month. The Realmuto acquisition would have been a successful one for the Phils regardless of whether they managed to re-sign him; trading for Realmuto during his arbitration years is a separate decision from the one to sign him to a long-term deal in free agency. Still, the Phillies acquiring Realmuto two years ago certainly couldn’t have hurt their chances of winning the bidding for him this winter.

The Marlins’ end of the deal is a bit more uncertain (as one would expect when a team trades away an established star for a group of talented younger players) but certainly looks bright. Sánchez was seen as the prize of the package at the time of the deal, and he’s only elevated his stock since then. The young righty spent most of the 2019 season in Double-A, where he was very good, and then made his MLB debut last season.

Over his first seven starts at the big league level, Sánchez pitched to a 3.46 ERA/4.18 SIERA. His strikeout rate (20.9%) was a bit below-average, but Sánchez posted better than average marks in both walk rate (7.0%) and ground ball rate (58.0%) as a 22-year-old. It may be too early to definitively declare the flamethrower a future ace, but he’s clearly a central piece of a young rotation the Marlins hope will allow them to perennially reach the postseason, as the Fish did in 2020.

Alfaro and Stewart remain in the Miami organization, but their respective stocks have fallen since the trade. After a decent 2019 season, Alfaro struggled in 2020 and was eventually supplanted on the depth chart by Chad Wallach. Stewart, meanwhile, had a difficult 2019 season in High-A. Eligible for this offseason’s Rule 5 draft, Stewart was left off Miami’s 40-man roster but went unselected.

Even if neither of the secondary pieces in the deal become core pieces for the Marlins, the Realmuto-Sánchez central framework of the trade will be fascinating to follow. There figures to be plenty of times for broadcasters and fans to rehash the details of the blockbuster when the two square off against one another over the coming years.

At the time, Cruz was coming off an incredible four-year run with the Mariners. He had hit .284/.362/.546 during his time in Seattle. By measure of weighted runs created plus, the slugger was the sport’s eighth-most productive hitter between 2015-18 (minimum 600 plate appearances). Nevertheless, Cruz’s age and lack of defensive value as a full-time designated hitter limited him to a single year guarantee.

After a surprising Wild Card berth in 2017, the Twins slumped to a 78-84 season in 2018. Surely, the front office hoped that signing Cruz would install an elite bat into the middle of the order and help Minnesota’s lineup emerge as one of the best in the league. That’s precisely how things played out.

If anything, the already-great Cruz took his offensive game to another level in 2019. He hit a career-best .311/.392/.639 with 41 home runs in just 521 plate appearances. As a team, Minnesota slugged a record 307 homers that year en route to an AL Central title. That made exercising the 2020 option a no-brainer. Cruz again mashed at an elite level and helped the Twins to their second consecutive division championship this past season.

Now 40 years old, Cruz is again a free agent, facing the same questions he faced last time he was on the open market (and the time before that). He offers nothing defensively and is among the oldest players in the sport. Yet Cruz has shown no signs of decline at the plate; on the contrary, he’s coming off arguably the two best offensive seasons of his career.

Another deal between the Twins and Cruz makes plenty of sense. Minnesota again looks like one of the best teams in the American League, although the pursuit of another division title looks more difficult than ever thanks to the White Sox’s emergence as a legitimate contender. The past two division crowns haven’t led to any postseason success, which the Twins no doubt hope to change in 2021.  The parties have remained in contact this winter. No deal has come together to this point amidst uncertainty about whether the DH will expand to the National League, which would obviously open up Cruz’s market.

Injuries have been an all-too-common problem for Harvey, who underwent Tommy John surgery on his pitching elbow in October 2013 and sat out all of of the next season. Harvey made a triumphant return to win NL Comeback Player of the Year honors in 2015 – the latest season in which the Mets went to the World Series – but it wasn’t a campaign devoid of controversy for the hurler who became known as the Dark Knight. He and agent Scott Boras pushed for a limit of 180 innings for the year, but Harvey ended up exceeding that amount with ease, tossing 189 1/3 frames in the regular season and racking up another 26 2/3 in the playoffs. The workload may have been too heavy for his taste, but Harvey was actually great that October – including an eight-inning, two-run effort in a Fall Classic-deciding, Game 5 defeat to the Royals. Little did anyone know that shining moments would be so few and far between for him since then.

Rewinding to 2016, you’d have a hard time finding many regular starters who have been worse than Harvey. He underwent thoracic outlet surgery in July of that year, and that now looks like a death knell in hindsight. Now 31 years old, Harvey’s the owner of a 5.56 ERA – the third-highest figure among all qualified starters – in his most recent 390 innings.

Having seen enough of Harvey, the Mets – once justified in believing he was a true ace – gave up on him exactly two years ago. It was on May 8, 2018, that the Mets traded Harvey to the Reds for catcher Devin Mesoraco – another once-promising player who didn’t pan out as hoped. Harvey turned out OK as a Red, contributing 128 innings of 4.50 ERA ball en route to an $11MM guarantee with the Angels during the next period of free agency. Likewise, Mesoraco wasn’t horrible as a member of the Mets, with whom he batted .222/.306/.409 in 229 plate appearances. But neither player is even in baseball at this point.

Mesoraco has all but retired after sitting out the 2019 campaign. Harvey could still resume his career, but it’s not looking good. The former front-end starter was so ineffective in his lone year with the Angels that they released him in July. Harvey did catch on with the Athletics on a minor league contract after that, but he didn’t crack their big league roster at all, and there have been few rumblings about him since he elected free agency at the outset of offseason. In fact, MLBTR’s archives have just two somewhat recent news items on Harvey – one on how he auditioned for the Blue Jays as a reliever during the winter and another saying the Mets aren’t interested in reuniting with him. It’s a stunning descent for a pitcher who was among the best during his Mets heyday.

Photo courtesy of USA Today Sports Images

Martinez’s issues were ultimately sorted out after the Boston deal collapsed, and St. Louis has been the beneficiary. After a torrid run through the minors, Martinez ended up debuting in the majors in 2013 as a hyped prospect, even making five appearances in relief against Boston in St. Louis’ World Series loss to the Red Sox. He has since established himself as a key part of the Cardinals’ pitching staff.

Martinez truly broke out as a starter in 2015, the first season of a three-year, 580-inning stretch in which he logged a 3.24 ERA/3.59 FIP with 8.92 K/9, 3.17 BB/9 and a 54 percent groundball rate. The Cardinals made a sizable commitment to Martinez after the second of those seasons, signing him to an extension worth a guaranteed $51MM over five years in February 2017. Martinez is down to his last two guaranteed seasons on that pact, though the Cardinals will be able to control him for 2022 and ’23 via club options; that is, if they’re willing to pay him $17MM in the first year and/or $18MM in the second (otherwise, they could buy him out in either season for $500K).

Martinez seemed to be on pace to have those options picked up just a couple years ago, but it’s less clear what his future holds at this point. Now 28 years old, Martinez spent the majority of the previous two seasons as a reliever – an effective one at that – owing in part to injuries. Dating back to 2018, he has tossed 167 innings of 3.13 ERA/3.34 FIP ball with 9.16 K/9, 4.2 BB/9 and a typically above-average grounder percentage of 51.1.

All 48 of the hard-throwing Martinez’s appearances last year came out of the Cardinals’ bullpen as he recovered from shoulder issues, and he even converted 24 of 27 save opportunities while filling in for the injured Jordan Hicks as their closer. However, before the coronavirus pandemic reared its ugly head and caused baseball to shut down, the 28-year-old looked as if he was on track to return to his prior role in the St. Louis rotation in 2020.

No matter which job Martinez takes on this season (if there is one), it’s fair to say his production as both a starter and a reliever has been a boon to the Cardinals. Ten years ago today, they landed a two-time All-Star for a relative pittance.

Phillips entered the pro ranks as a high draft selection of the Montreal Expos, who picked him in the second round (No. 57) in 1999. He was later part of a Montreal-Cleveland deal that had a massive impact, as the Expos sent Phillips, Grady Sizemore, Cliff Lee and Lee Stevens to the Indians for Bartolo Colon and Tim Drew. Sizemore and Lee became stars in Cleveland, but Phillips didn’t amount to much there in 462 combined plate appearances from 2002-05.

Phillips spent the majority of his final season as a member of the organization with the Indians’ then-Triple-A team in Buffalo, where he put up a .734 on-base plus slugging percentage. Unimpressed, the Indians and former general manager Mark Shapiro soon gave up on Phillips. That proved to be a mistake, at least when you consider what they received for Phillips. Stevens never even pitched for the franchise, instead throwing a combined 37 1/3 innings with the Cubs from 2009-11 after the Indians traded him as part of a deal for utilityman Mark DeRosa (notably, that transaction also saw Chris Archer head to Chicago). While DeRosa was effective for the Indians in ’09, that was his lone season with the club. The team later sent him to to St. Louis in a trade for reliever Chris Perez.

Perez had his moments in Cleveland, but they don’t match up to Phillips’ impact in Cincinnati. “Dat Dude” was a productive Red from the jump and eventually became a franchise icon – someone who was instrumental in breaking their 14-year playoff drought in 2009. The Reds went on to earn two more playoff berths while Phillips was in their uniform. His long tenure with the franchise concluded in February 2017 with a trade to the Braves, but not before Phillips racked up a laundry list of personal accomplishments. As a member of the Reds, Phillips made three All-Star teams, won four Gold Gloves and batted .279/.325/.429 with 191 home runs, 194 stolen bases and 28.1 wins above replacement over 6,899 plate appearances. He’s currently eighth in Reds history in games played (1,614) and PA and 10th in hits (1,774), runs scored (877) and total bases (2,722), to name just a few key statistics.

Phillips, now 38 years old, hasn’t played in the majors since 2018. But he’ll always be a part of the Reds’ rich history, and his acquisition was no doubt one of the shining moments of former Reds GM Wayne Krivsky’s stint. It’s also another bit of proof that you shouldn’t sleep on any transaction, no matter how minor it may seem at the time.

Photo courtesy of USA Today Sports Images.

Holland entered free agency off a nice 2017 showing in Colorado, where he led the National League in saves (41) and logged a 3.61 ERA/3.72 FIP with 10.99 K/9 and 4.08 BB/9 over 57 1/3 innings. Not dominant numbers overall, but Holland picked up his third All-Star nod and was quite strong outside of a couple of blowups. Plus, the fact that it was his first action after a serious injury made his production look even better.

Holland’s best known for putting up excellent numbers in Kansas City from 2011-15, and he was close to untouchable during the Royals’ pennant-winning 2014 campaign. The decline began after that, though, as Holland suffered a torn right ulnar collateral ligament that ended his 2015 season in September. The injury prevented him from aiding the Royals in their run to a World Series championship that fall, forced Holland to undergo Tommy John and then caused him to sit out all of the next season.

Both the Rockies and the Cards were clearly impressed by the post-surgery Holland in 2017. He turned down his half of a $15MM mutual option after the season, but the Rockies then issued him a $17.4MM qualifying offer. Holland also said no to that, which may have been a mistake; however, expectations were that he’d beat that guarantee on the open market. MLBTR forecast a four-year, $50MM guarantee for Holland, but it turns out that he was not among the several free-agent relievers that winter who found a lucrative multiyear contracts (former Royals bullpen mate Wade Davis, who took Holland’s place in Colorado, led the way). Unfortunate for Holland, but considering the way his career has gone since then, the rest of the league’s teams dodged a bullet.

Because he didn’t sign until a couple days after the Cardinals’ season began, Holland did not have the benefit of a normal spring training. He took a bit of time to ramp up and then debuted with St. Louis on April 9, which proved to be his first of several poor outings with the club. Holland took the loss in that game after walking four of the five batters he faced. Walks were an all-too-common problem throughout Holland’s brief run as a Cardinal, as he wound up posting an extremely unusual and hideous line consisting of a 7.92 ERA with 7.92 K/9 and 7.92 BB/9. Holland never even registered a save for the club, which cut ties with him on Aug. 1, 2018, and ate almost $5MM in the process. To worsen the blow for the Cardinals, because Holland was a QO recipient, they had to cough up their second-round pick in 2018 and $500K of international money for inking him.

To his credit, Holland quickly rebounded from his abysmal Cards career. He closed 2018 in outstanding fashion as a member of the Nationals, with whom he recorded an almost flawless 0.84 ERA in 21 1/3 innings. Holland couldn’t follow that up in 2019, however, as he ended up with mediocre stats as a Diamondback. And they, like the Cardinals a year before them, designated Holland for assignment before the season concluded.

The 34-year-old Holland is now once again looking to rebound, this time back in his old Kansas City stomping grounds after the Royals reunited with him on a minor league contract in January. Perhaps Holland will revive his career either in KC or elsewhere in 2020, but the fact that he settled for a non-guaranteed deal two years after receiving such a sizable payday shows how far he has fallen.

Pettitte retired after the 2010 season, his 16th in the majors and his 13th as a Yankee, but felt the urge to pitch again while working as a spring guest instructor for the team prior to the 2012 campaign. As one of the most accomplished pitchers in the history of the organization, the Yankees were happy to welcome back Pettitte, then 39 years old, even though they already had six other arms (CC Sabathia, Michael Pineda, Hiroki Kuroda, Phil Hughes, Freddy Garcia and Ivan Nova) for five rotation spots. But it turns out that they needed Pettite that year. Pineda didn’t pitch after succumbing to a torn labrum following the Pettitte reunion, while Garcia and Nova turned in ineffective seasons.

As someone who signed so close to the regular season, Pettitte took time to ramp up before his return to the mound became official. He didn’t make his 2012 debut until May 13, a 6-2 loss to Seattle in which he yielded four earned runs on 6 1/3 innings.

Pettitte was encouraged afterward, though, saying: “I just cannot believe how comfortable this is for me. I don’t know how to explain it.”

Indeed, while Pettitte’s first game back didn’t produce ideal results for him or his team, he returned to his old ways from that point forward. Pettitte tossed eight shutout frames five days later in a 4-0 win over the Reds. He continued to throw well in the coming weeks, but Pettitte fractured his left fibula in a June 27 start versus Cleveland and didn’t get back until the end of September. Pettitte posted three solid outings to conclude the season, ending it with 12 starts and 75 1/3 frames of 2.87 ERA ball with a lofty grounder percentage of 56.3 and 8.24 K/9 against 2.51 BB/9. His stellar performance contributed to a 95-victory, AL East-winning campaign for the Yankees, who edged out the Orioles by two games.

The Yankees couldn’t have realistically asked for more out of Pettitte, but he provided it in October. Typically impervious to the pressure of the postseason, Pettitte combined for 13 2/3 innings of five-run pitching in two starts (one against Baltimore, the other versus Detroit). The Yankees did get by the Orioles in an ALDS that went the distance, but the Tigers overwhelmed them in the ALCS in a four-game sweep.

While Pettitte was unable to claim his sixth World Series title in his first season back, he fared so nicely that it convinced him to stick around for one more year. The Yankees had to pay up that time, inking the three-time All-Star to a $12MM guarantee, but they also got their money’s worth in 2013. Even though New York finished 85-77 and didn’t qualify for the playoffs, Pettitte’s going-out party was one of the highlights of the team’s year. He put the exclamation point on his career with a complete game, one-run performance in Houston (where he pitched from 2004-06) in his last game.

Thanks to Pettitte’s decision to end his first retirement on March 16, 2012, he spent two years further cementing himself as one of the top pitchers in the Yankees’ storied history.