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These Players Can Exit Their Contracts After 2020

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No matter if a Major League Baseball season takes place in 2020, there are certain players who will be in position to decide whether to exit their current contracts next winter. Whether it be by way of an opt-out clause or a mutual option, here’s a look at the players who will be able to choose to take their chances in free agency…

Opt-Outs

Back when the Marlins extended outfielder Giancarlo Stanton on a historic pact worth $325MM over 13 years in 2014, they included a one-time opt-out for next winter. Stanton has put up at least one phenomenal season since he signed that deal – he won the NL MVP and hit 59 home runs in 2017 – but injuries have hampered him on a regular basis. He’s now a member of the Yankees, who acquired him in a December 2017 deal, but Stanton played in just 18 games last season. He’ll still be owed $218MM for seven years after this season, and for at least the time being, it’s very tough to think of Stanton leaving that money on the table to test free agency.

Designated hitter J.D. Martinez, a member of the Yankees’ archrival in Boston, will have two years and $38.75MM remaining on his contract after this season. He’ll be 33 then, and will continue to be someone who’s known as a defensive liability, so should be opt out? It’s up for debate. The big-hitting Martinez remains an offensive standout, but his production last season fell (granted, he did still slash .304/.383/.557 with 36 home runs in 657 plate appearances). He subsequently chose not to opt out after last season, as doing so would have cost him his $23.75MM salary for this year.

One of Martinez’s former Tigers teammates, outfielder Nicholas Castellanos, will also have to choose whether to revisit free agency next offseason. Castellanos is another defensively challenged slugger, one whom the Reds guaranteed $64MM over four years this past winter. He’ll be 29 by the time the 2021 season rolls around, and by saying goodbye to his Reds pact, he’d be leaving $48MM on the table (including a $2MM buyout in 2024). It’s not easy to determine whether that will happen; some of it depends on how well Castellanos fares in 2020, if a season occurs. Carrying over the tremendous production he posted late last season after the Cubs acquired him from the Tigers may make Castellanos more inclined to try his luck on the market again, but his output at the plate has been more good than great throughout his career.

Mutual Options

For the most part, mutual options don’t get picked up. Either a player’s so effective that he opts for free agency or he’s not useful enough for his team to exercise the option. Rockies first baseman Daniel Murphy and reliever Wade Davis are among those who have mutual option decisions waiting after the season, but they’ve struggled in the club’s uniform so far. With that in mind, Murphy’s on track for a $6MM buyout (as opposed to a $12MM salary), while Davis figures to receive a $1MM buyout instead of a $15MM payday.

Brewers outfielder Ryan Braun ($15MM mutual option, $4MM buyout), Diamondbacks right-hander Mike Leake ($18MM mutual option, $5MM buyout) and Cubs lefty Jon Lester ($25MM mutual option, $10MM buyout) could also find themselves looking for new contracts next winter. The same goes for Mets reliever Dellin Betances, though it’s tougher to say in his case. The former Yankee barely pitched at all season on account of injuries, and if there isn’t a season in 2020, would he turn down a guaranteed $6MM in 2021? And would the Mets buy him out for $3MM? That’s one of the many interesting questions we could face next offseason.

Red Sox Notes: Sale, Opener, Eovaldi, Martinez, Downs

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Red Sox chief baseball officer Chaim Bloom declined to speculate on the status of southpaw Chris Sale before getting final word from the doctors. Sale underwent an MRI today for a sore elbow. As Eduardo Encina of the Tampa Bay Times covers via Twitter, Bloom acknowledged “concern” but also said that, “hopefully, it is just a bump in the road.” The team does have some information beyond what is known publicly; as Peter Abraham of the Boston Globe notes on Twitter, team doctors have already had a look at the imaging. But it seems that we’ll have to await the assessment of Dr. James Andrews before learning of Sale’ fate.

More from the Boston organization …

  • Even before this worrisome situation arose regarding Sale, the Red Sox have been toying with the idea of utilizing a starter at time in the upcoming season. As MLB.com’s Ian Browne reported recently, Bloom has been working with manager Ron Roenicke to work through the possibilities for employing such a strategy. Roenicke says the reasoning behind the concept is largely a reflection of the “personnel” available. Clearly, any lengthy absence from Sale would only increase the appeal.
  • On the positive side, the Sox have seen some encouraging signs from Nathan Eovaldi. As Browne further reports, the embattled righty says he “feel[s] really good” and believes his “mechanics are really good right now.” The results have been there to this point, not that there’s much sense putting too much stock in two spring appearances. But the Boston organization has to hope that the 30-year-old can sustain some momentum after a 2019 campaign in which he stumbled to a 5.99 ERA in 67 2/3 innings.
  • Veteran Red Sox slugger J.D. Martinez held forth on a few labor topics with WEEI.com’s Rob Bradford. The star expressed concern with the incentives teams have in constructing rosters. By his reckoning, baseball is “losing a lot of fans because teams are more motivate to lose than they are to win.” Martinez suggests that the competitive balance tax has had the opposite of its intended effect. He advocates for a “floor tax” by which teams would be penalized for under-spending. Ultimately, says Martinez, the game must “figure out a way to reward teams for competing and not reward them for losing” — or risk fading in relevance.
  • Infield prospect Jeter Downs was dropped into the Boston spotlight when he was included as a major component of the (re-formulated) Mookie Betts swap. As Jen McCaffrey of The Athletic writes (subscription link), the Sox are getting a player who’s known more as a dedicated grinder than for his flash. Though Downs wasn’t in the initial iteration of the Betts deal, he wasn’t an afterthought. It seems the Red Sox have long had eyes for the 21-year-old and were particularly impressed by some mid-2019 tweaks that both reflected Downs’s attention to detail and raised his foreseeable ceiling as a hitter.

AL Notes: Devers, Kopech, Martinez, Rangers

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We’re coming up on the three-year anniversary of the White Sox–Red Sox Chris Sale blockbuster. It’s tough to say either team regrets that deal at this point. Sale was instrumental in Boston’s 2018 World Series run and remains one’s of baseball’s best pitchers. Chicago, meanwhile, has reaped the benefits of a Yoán Moncada breakout season that saw him garner a down-ballot MVP vote. Michael Kopech, meanwhile, remains one of the sport’s most exciting young pitchers.

That pair (along with Luis Alexander Basabe and Victor Diaz) weren’t the only Boston farmhands the White Sox were targeting. At one point, Chicago asked for Rafael Devers, then a 20 year-old in High-A, Chicago general manager Rick Hahn tells David Laurila of Fangraphs. Suffice it to say, Boston has to feel good about rebuffing Devers’ potential inclusion, as he garnered even more MVP support than did Moncada after a breakout 2019 of his own. There’s no indication Devers talks ever got close, it should be noted, but it’s still an interesting counterfactual given the star player he has since become. Some more from the American League:

  • Speaking of Kopech, Hahn tells Laurila the fireballer is progressing as expected in his return from Tommy John surgery. The 23-year-old, who went under the knife in September 2018, logged a few innings in instructional league and enters the offseason fully healthy, per the GM. The club will no doubt be careful not to overwork the prized right-hander next season, but he seems on track to be a key factor in Chicago’s rotation mix. Kopech had dazzled in Triple-A in the two months preceding his big league call-up.
  • J.D. Martinez opted into his three-year, $62.5MM deal with the Red Sox earlier this month. Rob Bradford of WEEI hears that decision wasn’t an especially difficult one, “hardly coming down to the wire.” That seemingly reflects some tepidness among potential Martinez suitors as agent Scott Boras explored the star hitter’s market in advance of the decision. Speaking entirely speculatively, that could tamp down the likelihood of Martinez opting out after next season (at which point he’ll have to decide on a two-year, $38.7MM deal) or of the Sox finding a buyer if they look to shop Martinez this offseason as a means of cutting payroll. That said, Martinez remains an elite hitter, and other teams’ circumstances and interest can no doubt change in the coming months.
  • The Rangers unveiled a new $12.5MM academy in the Dominican Republic Friday, reports Evan Grant of the Dallas Morning News. As Grant details, the facility is a significant step forward from previous conditions for Texas’ international signees. The Rangers’ front office believes that improving conditions for their youngest prospects will help them flourish on the field; current MLB first baseman Ronald Guzmán tells Grant that in the team’s previous cramped facility, illnesses spread among players quickly, which could no doubt have an adverse impact on players’ performance. Independent on any on-field benefits they’ll reap, the organization deserves credit for improving conditions for its players.

Boras On Free Agency, Cole, Strasburg, Castellanos, JDM

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Major League Baseball’s previous couple offseasons didn’t necessarily favor the players. Some free agents sat on the open market far longer than expected, while others signed for less than expected or didn’t receive guaranteed contracts (or any deals) at all. Count the game’s most famous agent, Scott Boras, among those disgusted with the way free agency has gone in recent years, as Bob Nightengale of USA Today details. Speaking at this week’s GM meetings, the always colorful Boras lamented the lack of teams going all-out to win, saying that “the industry is in a competitive hibernation, and the fans are reacting to it,” referring to drops in attendance (as Nightengale notes, even the Nationals, Astros and Yankees drew fewer fans).

“We got a decline in attendance. We got owners charging more for generations that want to see the game, while we’re losing a generation of young people that are only interested in competition,” said Boras. “Clubs feel there are greater rewards for losing than winning. And there is nothing to drive them to win because they don’t think it’s smart.’’

Boras even took aim at current commissioner Rob Manfred, whom he criticized for finding the luxury tax and the present system as a whole “wonderful.” That system, in Boras’ estimation, is “corrupt,” as it fails to “properly place progressive values of players at all. It’s always regressive.”

Of course, Boras’ hope is that the system doesn’t penalize his newest free-agent clients. And he’s representing several prominent players now on the open market, including superstar right-handers Gerrit Cole and Stephen Strasburg and outfielder Nicholas Castellanos. Boras is also the agent for Red Sox J.D. Martinez, who elected against opting out of the remaining three years and $62.5MM on his contract. The agent discussed those clients this week.

In regards to Cole, who looks likely to smash David Price’s record guarantee of $217MM for a pitcher, Boras stated (via Matt Breen of the Philadelphia Inquirer): “If this were major-league Christmas, we would be looking at 30 stockings that clearly wanted a lump of Cole. I think starting pitching has become back in vogue. It’s an aggressive market.”

Boras also represents outfielder Bryce Harper, who signed the largest deal ever for a free agent last winter at 13 years and $330MM. He opined that Cole and Strasburg are in line to have even more teams after them than Harper did last offseason, per Breen. And while there has been speculation that Cole, a Southern California native, wants to sign with a West Coast team, that’s not necessarily the case.

“I don’t think geography matters to any of these guys as much as the continuance of winning and being able to achieve their goal of getting that rare ring,” Boras said. “And I think in Gerrit’s case, when you’re that close, you’re looking at this process as one where I’ve got a box to check and I want to go out and put together the best effort to put me in that position to do that.”

You wouldn’t expect Boras to say anything else in this case, as doing so could have decreased his client’s earning power. But, regardless of whatever geographic preference Cole may or may not have, the East Coast-stationed Phillies will heavily push for him, Breen reports. They won the bidding for Harper a year ago, and though general manager Matt Klentak has suggested he’s averse to signing more free agents saddled with qualifying offers (as Harper was, and as Cole is), Cole would greatly help a Phillies rotation in dire need of front-end aid.

The Phillies are among the teams that may be in the market for “a lump of Cole,” but that wasn’t the last of Boras’ holiday-themed metaphors. In regards to Castellanos, he stated (per Patrick Mooney of The Athletic): “Old Saint Nick delivers once a year. Young Saint Nick delivers all season. So you’ve got a pretty good market for that kind of player.”

Whether “young Saint Nick” (Castellanos) really “delivers all season” is debatable. He’s clearly a flawed player, one who has been more good than great at the plate throughout his career and has clearly struggled defensively in the outfield and at third base. Nevertheless, as a 27-year-old who does bring an above-average bat to the table, expectations are that he will fare well in free agency. MLBTR has him landing the eighth-highest guarantee of anyone on the market – a four-year, $58MM deal. 

Martinez is something of a souped-up version of Castellanos, but he’s a half-decade older (32) and perhaps even a less viable defender. No doubt, Martinez would have had difficulty outdoing the money left on his pact had he opted out. Boras addressed Martinez’s decision, saying (via Alex Speier of the Boston Globe): “J.D. wanted assurance of competition at a high level and the fact that he played so well in Boston, we looked at it and with those two things in mind, we wanted to make sure that was the focus and for that reason he decided to opt in. The contract we structured allowed him choices after each season so it was something that, in this year at this time, we felt really that was the best decision.”

As Boras noted, Martinez will have another chance to opt out after next season. In the meantime, Boras is sure to focus his attention on several other clients who – despite his (arguably justifiable) distaste for the current system – could break the bank in the coming months.

Red Sox Notes: JDM, Betts, Trades, Porcello

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Red Sox president and CEO Sam Kennedy felt J.D. Martinez’s opt-out decision “was a hard one to read” and “I honestly thought it could go either way,” though Kennedy is obviously pleased to have Martinez back in the fold, MassLive.com’s Chris Cotillo writes.  Martinez’s choice will naturally have a big impact on Boston’s financial situation, particularly since the team is looking to shed some payroll and possibly get under the luxury tax threshold, though Kennedy was only focused on what Martinez’s return will mean for the club on the field.

“You never want to lose a talented player.  Of course, there are hard decisions teams have to make in terms of parting ways with guys in every sport,” Kennedy said.  “What J.D. Martinez has done for the Red Sox and hopefully will continue to do, is not just a big bat in the middle of the lineup.  He also helps elevate other players on the team and that’s widely documented.  That’s helpful.  That’s a good thing.  Now we move on.”

More from Fenway Park…

  • It isn’t yet known if Martinez staying will make it more likely that the Sox could trade Mookie Betts in order to solve their luxury tax issues, though Kennedy said (via Cotillo) the club is still hoping to enter into extension talks this winter.  “We love Mookie Betts….We’ve engaged in discussions with him and his representatives in the past and we’ll continue to engage with them,” Kennedy said.  No negotiations have taken place to date this offseason, which isn’t surprising given that most teams wait until closer to Spring Training to begin extension talks (plus, Chaim Bloom was only just hired as Boston’s new chief baseball officer).  While the Sox have been proactive in locking up in-house stars over the years, most recently inking Xander Bogaerts and Chris Sale to extensions last spring.  Betts, however, has been clear about his desire to test the free agency after the 2020 season, and with the open market now less than a year away, it remains to be seen if the Red Sox can get anywhere in convincing him to stay.
  • Whether Betts is part of a blockbuster deal or not, Bloom’s hiring would seem to indicate that the Sox will be much more active on the trade market under their new front office boss than they were under Dave Dombrowski.  Alex Speier of the Boston Globe notes that since the start of November 2016, when Bloom and Rays GM Erik Neander took over Tampa’s front office, the Rays swung 65 different trades.  In that same timeframe, the Sox made only 21 deals.  While the two franchises are obviously in quite different places in terms of payroll and roster creation strategy, it does stand to reason that trades may be a much larger part of Boston’s efforts to reshape the team.
  • Could a reunion with Rick Porcello be in the cards?  The Boston Herald’s Jason Mastrodonato looks at the pros and cons, noting that Porcello perhaps could have a rebound year and, at worst, will eat innings within a rotation full of injury question marks.  That said, Bloom (who has no past history with Porcello) could prefer to acquire a starter with a higher potential ceiling, and who’d cost less than what Porcello is likely to find on the open market.  MLBTR projects Porcello for a one-year, $11MM contract — no small amount for a Red Sox team that is ideally trying to avoid the luxury tax.

J.D. Martinez Will Not Opt Out Of Red Sox Contract

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Outfielder J.D. Martinez will not opt out of his contract with the Red Sox, per Jon Heyman of MLB Network (via Twitter). The 32-year-old Martinez had the option of collecting a $2.5MM buyout to forgo the remaining three years and $62.5MM on his contract but will instead once again serve as Boston’s primary designated hitter in 2020.

Martinez, signed to a five-year, $110MM contract prior to the 2018 season, enjoyed a career-year with in the first season of that deal, hitting .330/.402/.629 with 43 home runs. He followed that up with a terrific .304/.383/.557 slash through 657 trips to the plate.

That excellence at least created the possibility of Martinez opting out, but the market was also a poor one for Martinez, given the lack of contending clubs (or hopeful contenders) with an opening at designated hitter. The Astros (Yordan Alvarez), Angels (Albert Pujols/Shohei Ohtani) and Twins (Nelson Cruz), for instance, all have solidified options there. The Yankees have a number of options to rotate through their DH slot (Giancarlo Stanton, Aaron Judge, Luke Voit, Mike Ford and Greg Bird among them). Other clubs, including the Rays, Indians and incumbent Red Sox all face varying degrees of payroll issues. National League teams, surely, would be reluctant to issue a multi-year pact to a player with such defensive limitations.

Beyond the clearly sub-optimal market factors, Martinez will have another bite at the free-agent apple next year via a second opt-out provision in the aforementioned five-year deal. He’ll now earn $23.75MM in 2020 before having the opportunity to test free agency again next winter when he’ll have two years and $38.75MM remaining on his contract.

The decision has significant long-term ramifications for the team as well. Already, there have been rumors about the Red Sox shopping 2018 AL MVP Mookie Betts this winter as he heads into his final season of club control. Some of that is tied to the fact that the Betts has, to this point, insisted upon testing the free-agent market rather than explore a potential extension, but Boston’s luxury tax situation is also a clear factor. The Red Sox are currently $28MM over the luxury tax threshold, placing them firmly into the second tier of penalties. Had Martinez opted out of his deal, they’d have seen $22MM subtracted from that luxury ledger, but they’ll now likely search for alternative means of reducing their levels of penalization.

MLBTR Poll: Value Of Potential J.D. Martinez Contract

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The Red Sox just named a new chief baseball officer in Chaim Bloom, but he may already be facing the departure of one of the team’s best players. Designated hitter/outfielder J.D. Martinez will have a chance to opt out of the remaining three years and $62.5MM left on his contract within five days of the conclusion of the World Series, which could end Tuesday. Red Sox chairman Tom Werner recently met with Martinez’s agent, Scott Boras, though owner John Henry said afterward the club’s still not sure whether JDM will exit his contract in the coming days.

On one hand, if Martinez goes back to free agency, it could give Boston the type of financial relief it’s seeking. The team’s seemingly hoping to get under the $208MM competitive-balance tax threshold for 2020, so erasing Martinez from its list of guarantees would be a boon in that regard. On the other, it’s hard to imagine a Red Sox team that just missed the playoffs improving without Martinez in the fold. The 32-year-old is only weeks removed from the end of another excellent offensive campaign, in which he slashed .304/.383/.557 (139 wRC+) with 36 home runs in 657 plate appearances. Martinez’s results this year weren’t as tremendous as they were from 2017-18 with the Tigers, Diamondbacks and Red Sox, though he was still unquestionably one of the premier hitters in the game. Statcast backed that up, crediting Martinez with a .402 expected weighted on-base average that tied him with Aaron Judge for ninth in baseball.

It’s pretty clear Martinez can still hit at an elite level. Still, it’s not clear whether he should opt out. He’d be leaving a substantial amount of money on the table in doing so, which could be especially risky for a 30-something whom the Red Sox would saddle with a qualifying offer. There was no QO hanging over Martinez’s head when he signed with Boston for five years and $110MM entering 2018, as he was part of a midseason trade during the prior campaign. He wouldn’t be so fortunate this time, and with teams seemingly veering away from giving up draft-pick compensation for aging free agents, Martinez may be in for a disappointing trip to the open market. That’s particularly true when considering his lack of defensive value, which could largely limit Martinez’s market to American League franchises that could use him as a DH.

It’s obvious Martinez is no slam dunk to opt out, but whether he does will be one of baseball’s most interesting stories in the coming days. If Martinez does leave behind what’s left of his Red Sox deal, though, how well do you think he’d do on his next pact?

(Poll link for app users)

Latest On J.D. Martinez

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Red Sox chairman Tom Werner met recently with agent Scott Boras regarding the contractual status of slugger J.D. Martinez, as Christopher Smith of MassLive.com was among those to report, but there’s still no clarity as to whether Martinez will remain with the Boston organization for 2020 and beyond. Martinez can opt out of the three years and $62.5MM left on his contract, with a decision due five days after the conclusion of the World Series.

That’s one of several opt-out calls that Boras will be making with his clients. There have been some indications over recent months that Martinez is at least pondering a return to the open market. When we polled MLBTR readers late in the season, it came down as a fairly close call, with just under 57% of respondents expecting Martinez to stay in Boston.

Martinez’s representative did not give the Red Sox a clear impression as to his current thinking, per owner John Henry. Neither did the team express any interest in hammering out a new deal that would override the in-or-out decision available to the veteran outfielder/DH. Given the club’s decision to pare back payroll, that’s not at all surprising. It’s quite possible that the club would rather Martinez walk, freeing up spending capacity to utilize in other, potentially more efficient manners. The ability to issue a qualifying offer and pick up draft compensation would also hold appeal.

That said, there’s no question the Red Sox are better with Martinez anchoring the lineup. The 32-year-old turned in a .304/.383/.557 batting line with 36 home runs in his second campaign in Boston. That wasn’t quite the monster showing he put up in 2017-18, but was still about forty percent better than the league-average hitter.

With just-inked chief baseball officer Chaim Bloom tasked with finding spending efficiencies to keep the BoSox competitive at a lower price point, it’d be surprising to see an expanded commitment to Martinez. But there was — and perhaps still is — at least a theoretical possibility of working out a new deal that spreads the cash owed over a lengthier stretch. But that would mean pushing deep into Martinez’s fourth decade, a decidedly risky proposition.

For much the same reason, it is far from clear that Martinez would benefit by opting out. As noted, his just-completed season was not especially excellent by his lofty standards. The qualifying offer would be a factor. The consensus among the MLBTR staff seems to be that Martinez might have trouble beating his remaining guarantee since there just isn’t a ton of obvious demand for players of his ilk on the marketplace. It’s possible to imagine him getting more money, but there’s certainly downside risk in an opt-out scenario.

It may well be that the sides will remain wedded for the time being. Boras already controls the market’s top names — including fellow opt-out candidate Stephen Strasburg — and would surely love the chance to dangle another top name when he’s making the rounds with ownership. But the super-agent has also shown ample respect (and disdain) for the power of the qualifying offer and knows the limits of earning power for aging, defensively limited hitters. In recent comments, Boras said he believes Martinez is capable of playing the corner outfield and certainly seemed to be launching his marketing campaign. But it’ll be a close decision and one that probably comes down to personal preference and risk tolerance on the part of Martinez.

Quick Hits: JDM, White Sox, Rays, d’Arnaud, 2011 Draft

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As we all look forward to Game 5 of the World Series, let’s run through some noteworthy items from around the baseball world…

  • Should Red Sox slugger J.D. Martinez elect to opt out of the three years and $62.5MM remaining on his deal, the White Sox look like the “consensus” top suitor for the 32-year-old’s services, Rob Bradford of WEEI relays. At this juncture, it seems unlikely that NL teams would enter the Martinez sweepstakes given his shortcomings as a defensive outfielder. Of course, the lack of an NL market severely restricts the potential market for Martinez, a factor that he’ll surely consider as he weighs whether to enter free agency. What’s more: if he does, he’ll come with a qualifying offer attached, meaning that a signing team would have to surrender a draft pick to sign him. All those things make it markedly more difficult to identify realistic landing spots for the hitting virtuoso, though the White Sox may stand above the rest.
  • As the Rays prepare to embark on the offseason, they’ll have to evaluate Travis d’Arnaud’s role in their 2020 catching situation, writes Marc Topkin of the Tampa Bay Times. The ex-Met emerged as a surprising offensive contributor after he was acquired in a nondescript May trade, ending the season with a .782 OPS for the Rays. Fellow catcher Mike Zunino’s fate might depend on what happens with d’Arnaud, who has a chance to earn a two-year deal at a $6MM or $7MM AAV. If the Rays choose to keep him around at that price, Zunino may become expendable after a disappointing offensive season. Meanwhile, letting d’Arnaud walk would put pressure on Zunino to improve on the dreadful .544 OPS he posted in his first season with the Rays. Otherwise, the team could once again turn to external options.
  • When it’s all said and done, the 2011 first-year player draft may go down as one of the best in baseball history, writes Dan Connolly of The Athletic. It’s a timely retrospective, with the stars of the class on full display in this year’s World Series: the Astros’ George Springer and Gerrit Cole, as well as the Nationals’ Anthony Rendon, all came from the 2011 first round (Cole and Rendon, it’s worth noting, will also be the offseason’s two most sought-after free agents). Trea Turner, meanwhile, was a 20th-round choice the same year. And that’s not to mention the bevy of stars that play elsewhere in the Majors: Mookie Betts, Trevor Bauer, Francisco Lindor, and Javier Báez all come from the ranks of the 2011 draft, which also featured “what-if” stories like Dylan Bundy and the late José Fernández. Connolly also considers the pivotal selection of Danny Hultzen by the Mariners, which could have had a profound effect on the rest of the draft had they instead opted for Rendon, their second choice. The 2011 draft has already earned its place among the all-time great draft classes, which is doubly impressive considering that it’s collectively still in its prime years.

Red Sox CEO On Betts, JDM, Luxury Tax

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Red Sox CEO Sam Kennedy met with the media for a postmortem on the 2019 season Monday. At a time when the future of superstars Mookie Betts and J.D. Martinez is uncertain — Betts is a free agent after 2020 who has repeatedly voiced a desire to test the open market, while Martinez can opt out of the final three seasons of his contract next month — Kennedy acknowledged that there “is a way” to keep both Betts and Martinez on the roster but added that doing so “will be difficult” (Twitter links via Alex Speier of the Boston Globe).

Such comments only figure to fuel speculation that Betts could be made available in a what would be a blockbuster trade this winter, although the Sox have given no firm indication that he’ll be shopped. Betts earned $20MM this season in just his second trip through the arbitration process, and it’s likely that his salary will jump into the $30MM range next year. Betts didn’t replicate last year’s MVP production nevertheless put together yet another brilliant all-around season. In 706 trips to the plate, the 26-year-old batted .295/.391/.524 with 29 home runs, 40 doubles, five triples and 16 stolen bases. He posted flat-out elite defensive marks, per virtually every metric, for the fourth consecutive season, as well: +16 Defensive Runs Saved, +13.3 Ultimate Zone Rating, +7 Outs Above Average.

As for Martinez, he’s signed for another three years at a total of $62.5MM. He’ll receive a $2.5MM buyout if he opts out of the deal this offseason, meaning he’d need “only” to top a three-year, $60MM commitment in free agency in order to come out ahead. That’s not a given, as he’d surely be hit with a qualifying offer and face some questions about his defensive abilities (or lack thereof) when negotiating with National League clubs. But, asked just last night about sticking in Boston or searching for what would perhaps be his fifth team in five seasons, Martinez replied that he “kind of like[s]” moving around and wouldn’t mind doing so again if need be.

Payroll became an issue with the Red Sox last year when the team was quite clearly doing everything in its power to avoid crossing the third and final luxury tax threshold in free agency. Boston did nothing to address its bullpen outside of some low-profile rolls of the dice, and the team’s lack of bullpen depth proved costly in the long run. Still, significant additions would’ve come with a 75 percent dollar-for-dollar luxury hit, and the Boston ownership group demonstrated that even an organization with that level of deep pockets has its limits.

The Red Sox currently have “only” about $151MM counting against their luxury tax bill in 2020. That’s well south of the $208MM cutoff for the baseline luxury threshold, but that $151MM projection only includes currently guaranteed contracts. In other words, it doesn’t yet factor in arbitration raises for players whose salaries have yet to be determined. Not only will Betts be in line for an enormous raise on this year’s $20MM salary, but the Red Sox will also need to negotiate raises for Eduardo Rodriguez ($4.325MM in 2019), Brandon Workman ($1.15MM), Jackie Bradley Jr. ($8.55MM), Sandy Leon ($2.475MM), Steven Wright ($1.375MM), Matt Barnes ($1.6MM), Heath Hembree ($1.3125MM) and Andrew Benintendi ($717K). Obviously, some of those players could be traded or non-tendered, thus eliminating the need to worry about potential raises.

One of the biggest questions facing ownership is whether the team is comfortable paying the luxury tax for what would be a third consecutive season. The number of successive seasons is important, because penalties escalate with each consecutive year above the line. As a third-time offender, the Red Sox would be subject to a 50 percent luxury tax for every dollar spent over $208MM. They were taxed at a 30 percent rate in 2019 and 20 percent in 2018.

Kennedy plainly stated today that dropping beneath the luxury tax base of $208MM is a “goal but not a mandate” (Twitter link via Speier). The Red Sox, of course, are in the process of seeking out a new leader for their baseball operations department after firing Dave Dombrowski earlier this month, but the quartet that is heading up baseball ops an on interim basis — assistant GMs Eddie Romero, Brian O’Halloran, Zack Scott and Raquel Ferreria — have discussed scenarios in which they’d exceed the luxury tax in early discussions surrounding the team’s offseason approach and 2020 plans.

Obviously, the health and well-being of the team’s top two starting pitchers will be paramount not only when forecasting the team’s 2020 playoff chances but also in determining what types of additions need to be made over the winter. To that end, O’Halloran informed reporters today that the club anticipates both Chris Sale and David Price will be ready for Spring Training. If so, they’d return to join right-hander Nathan Eovaldi and the aforementioned Rodriguez. Complicating matters for the Sox is that each of Sale, Price and Eovaldi delivered mixed results, at best, throughout injury-shortened seasons and now represent question marks more than sure things. Not only will the team need to foster some additional depth, but adding a reliable source of innings to help round out the rotation seems likely to be a goal.

If the Sox do indeed aspire to dip back below the tax line, then there could be a wide-ranging series of changes to the roster this winter. However, nothing from today’s press conference seems to suggest that any sort of rebuild is in the offing. O’Halloran noted that while resetting the luxury line at some point would obviously be beneficial, the club’s goal is to build a championship-caliber roster (Twitter link).

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