The World Series has ended, which means the offseason has begun. While every winter carries a lot of uncertainty, this one is especially fraught because of the looming fight over the expiring collective bargaining agreement.
“From our standpoint, there are a lot of things about that that we don’t control,” Red Sox chief baseball officer Chaim Bloom said late last month. “It will obviously dictate what we and the industry will do, but I think now as we’re making plans for the meat of (the) offseason once the World Series is over, we just need to be focused on those goals of building a winning club next year and beyond. How the time of this (is) going to unfold is anyone’s guess. We have to make sure we’re ready.”
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At the very least, the rest of this month provides some familiar guideposts to steer offseason decision-making. Here’s a bit of what to expect before the CBA fight potentially changes everything or thrusts the entire sport into darkness.
One day after the World Series: Players file for free agency
The market won’t open to everyone for five days — there’s a brief window in which players can negotiate only with their former teams — but this is basically the start of the offseason. The Red Sox have six players who will automatically become free agents.
Eduardo Rodriguez: An interesting case, because the Red Sox will undoubtedly be in the market for a starting pitcher, and E-Rod is a popular teammate who’s spent his entire big-league career in Boston. But the free-agent rotation market is pretty deep this winter. How aggressively will the Red Sox pursue their own lefty?
Adam Ottavino: Acquired in a Yankees salary dump, Ottavino was at times a vital part of the Red Sox pitching plan, and even when he wasn’t, he might have remained a crucial part of the bullpen. More than one young pitcher talked about his influence as a veteran mentor. That doesn’t mean he’ll be back, though.
José Iglesias: Played so poorly in the first five months that the Angels released him, then played so well in 23 games with the Red Sox that it’s legitimately worth wondering if the team might bring him back to be at least a part-time player at second base and shortstop.
Hansel Robles: An extra reliever acquired at the trade deadline, he wound up in Alex Cora’s circle of trust late in the season. Whether that’s enough to bring him back might depend on the cost.
Travis Shaw: A scrap-heap waiver claim brought back into the organization to provide some left-handed thump at first base. It kind of worked, actually, but that might not be enough to give him a big-league deal this winter.
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Danny Santana: Versatile and athletic, Santana had to settle for a minor-league deal last offseason, and his 57 OPS+ this season won’t exactly help him at the negotiating table.
(For financial purposes, it’s worth noting that Dustin Pedroia’s contract also comes off the books this offseason.)
Five days after World Series: Deadline for contract options and qualifying offers
Always an important deadline, but especially fascinating for the Red Sox this winter. They have a bunch of options to consider, and some of them are vitally important.
J.D. Martinez ($19.375 million player option): Martinez has the right to opt out of his contract’s final season. He elected to stay through his past two opt-outs, but now the potential of a universal DH might entice him to hit the open market. (Worth noting, at the time he has to make the decision, Martinez won’t know for certain whether the National League is adding a DH.)
Kyle Schwarber ($11.5 million mutual option): Even without an obvious place to play him, the Red Sox will presumably pick up their half of the option, while Schwarber seems likely to decline. He was just too good offensively and should be one of the most in-demand bats of the winter.
Garrett Richards ($10 million team option): If the Red Sox decline, they owe Richards a $1.5 million buyout. He had some great stretches this season, both as a starter and as a reliever, but $10 million might be a bit much.
Christian Vázquez ($7 million team option): Picking up this option seemed a no-brainer when the season started, but then Vázquez had a disappointing year at the plate. That said, good everyday catchers are hard to find — and they’re expensive — and at the team’s end-of-season news conference, Bloom sounded inclined to bring Vázquez back.
Martín Pérez ($6 million team option): The Red Sox declined a similar option last winter when Pérez was coming off an even better season. Presumably, they’ll decline again this winter.
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As for qualifying offers: The one-year deals reportedly are set at $18.4 million this winter (teams have to offer that much to be compensated if a free agent leaves). If Martinez opts out, it will be a no-brainer to extend him a qualifying offer, but $18.4 million might be too rich to offer Rodriguez, who this year made less than half that much. Because he was traded midseason, Schwarber is not eligible for a qualifying offer.
Sources: MLB clubs have been informed that the qualifying offer for free agents this winter is set at $18.4 million. That's down slightly from $18.9 million QO of last winter. Free agents extended a QO will accept or reject before the expiration of the current CBA Dec. 1.
— Buster Olney (@Buster_ESPN) October 12, 2021
Nov. 15-18: BBWAA awards
These are not particularly important, but they’re always notable and worth discussing. The Red Sox probably won’t win any of them, but they have viable candidates for all four.
Rookie of the Year: Teammates regularly touted Garrett Whitlock as a Rookie of the Year favorite, which was probably overstating his case (pretty hard for a reliever to make that kind of impression). Would be cool to see him finish in the top five, though.
Manager of the Year: If not for the baggage of his past transgressions, would Alex Cora be a favorite for this award? Doesn’t it often go to the manager whose team most exceeded expectations? Is that Cora or Scott Servais in Seattle?
Cy Young: Gerrit Cole and Robbie Ray seem to be the favorites, but Nathan Eovaldi did finish with the highest fWAR, fewest walks per nine and third-best xERA among American League pitchers. Can he finish in the top three?
MVP: Another top-10 finish for Xander Bogaerts, who ranks eighth in the American League in fWAR? Rafael Devers has never finished higher than 12th. Can he top that? Will Eovaldi or Kiké Hernández appear on any ballots?
Nov. 19: Rule 5 protection
Last winter, the Yankees faced a 40-man roster crunch that forced them to leave valuable players exposed to the Rule 5 draft. They crossed their fingers on Whitlock and ultimately lost him to their greatest rivals, who saw him transform into a seemingly elite young pitcher.
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Well, now the shoe is on the other foot, because it’s the Red Sox who face a roster crunch this winter. As always, the crew at SoxProspects does a wonderful job of keeping track of all the Rule 5 eligible players. We’ll single out these eight:
Jeter Downs (2B/SS): Rough year in Triple A but finished strong, then got off to an incredible start in the Arizona Fall League. Upside is too great to leave him exposed, especially given his versatility that could easily stick as a utilityman.
Bryan Bello (SP): One of the risings stars of the Red Sox system, he should be another lock for protection. Not out of the question that he pitches his way into the big-league mix next summer.
Gilberto Jimenez (OF): He’s very young (21, with only 94 games at the full-season level), but he’s also extremely talented, with a switch-hit and speed profile that could stick as a fourth or fifth outfielder. It would be very risky to dangle this level of talent.
Josh Winckowski (SP): Possibly the most important piece of the Andrew Benintendi trade, Winckowski showed enough this season to suggest he could be a viable big-league option in 2022.
Kutter Crawford (SP): Made his big-league debut this season, but because he was a COVID-19 replacement, he wasn’t actually added to the 40-man roster. The fact he was called up, though, shows the Red Sox take him seriously as a big-league option. Put himself on the map in his return from Tommy John surgery.
Durbin Feltman (RP): College closer was expected to be fast-tracked, but his professional career stalled in Double A in 2019. He got moving again with a strong 2021 split between Double and Triple A, but is he more than an up-and-down middle-inning arm?
Ryan Fitzgerald (utility): Undrafted infielder has performed too well to ignore. He’s credited with being a reliable defender, and he had an .862 OPS between Double A and Triple A this year. An obvious bench candidate if left exposed.
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Thaddeus Ward (SP): Is this the Red Sox version of Whitlock? Ward was terrific in 2019 and opened 2021 in Double A, but he had Tommy John surgery after just two starts. If the Sox don’t protect him, someone else could take Ward and let him rehab without needing to put him immediately on the active roster.
That’s already a lot of strong Rule 5 candidates to consider, and it’s to say nothing of pitchers Kaleb Ort, AJ Politi, Victor Santos and Frank German, or position players Kole Cotham, Pedro Castellanos and Ceddanne Rafaela. The Red Sox almost certainly will not have room for all of them, which means we could see some early maneuvering to trade away fringe players (Phillips Valdez, Ronaldo Hernández, Hudson Potts, Jeisson Rosario) to open spots on the 40-man roster for this next wave.
Dec. 1: Non-tender deadline
This typically affects arbitration-eligible players as teams can non-tender them rather than guarantee arbitration raises for next season. The Red Sox have eight arb-eligible players. Here’s the list with projected salaries from MLB Trade Rumors:
Rafael Devers ($11.1 million): Unless Bloom wants to burn the fan base to the ground with another trade, Devers will absolutely be back. Question is, will it be through an arbitration raise or a long-term extension?
Hunter Renfroe ($7.6 million): Part of the upside in signing Renfroe last winter was the remaining years of team control. His breakout season should lead to a sizable raise, but on a one-year deal, it’s surely worth it.
Alex Verdugo ($3.2 million): This should be his first year of arbitration eligibility. No chance he’ll be non-tendered.
Nick Pivetta ($3.2 million): Also an arbitration first-timer, with the same projected salary as Verdugo. Also no chance he’ll be non-tendered.
Kevin Plawecki ($2 million): A modest raise for a pretty good backup, unless the Red Sox choose to save some money and give Connor Wong a chance.
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Ryan Brasier ($1.4 million): Didn’t pitch much this season, but he did pitch well, and Alex Cora seems to like and trust him. If he was worth $1.25 million last winter, he’s surely worth $1.4 million this winter.
Josh Taylor ($1.1 million): He’s become a vital part of the bullpen and remains a bargain at this price.
Christian Arroyo ($1.1 million): Durability concerns are valid, but he was good enough at the plate and in the field for this to be a reasonable price, even if he’s only a part-time bench player.
Dec. 1: CBA expires
This is the most important date of them all. If baseball reaches this date without a new collective bargaining agreement in place, everything will come to a screeching halt. The Rule 5 draft should be Dec. 9 — the Red Sox have had success there the past two years — but at this point, who knows if or when that will actually happen? Everything after Dec. 1 is a total mystery because of the looming CBA fight, which could change everything.
Even the weeks leading up to that deadline carry less certainty than usual, because it seems anyone’s guess how the players and teams will respond to such a mysterious future. Do both sides rush to get deals done, or will they prefer to hold out and see if the new rules prove more advantageous? Will there be a lockout that ends in a mad rush to fill rosters? If there is a lockout, how long will it last? Everything beyond Dec. 1 is hazy at best.
(Photo of Chaim Bloom and Alex Cora: Jim Davis / The Boston Globe via Getty Images)
