The Red Sox were eliminated from the postseason in Game 3 of their wild card series against the Yankees, a game where Boston mustered just five hits all night and got a runner as far as second base exactly once.
Though the Red Sox did shoot themselves in the foot with base-running, fielding and bunting failures in Game 2, thus costing them their shot at reaching the ALDS, Game 3 was a bit more representative of the Red Sox and their weaknesses.
The starting rotation was thin, with Lucas Giolito’s ill-timed injury complicating matters, the lineup was weak, and the defense was weak. Ultimately, it all caught up to the Red Sox, and their winter has begun just as soon as October began.
The good news for the Red Sox is that they’re not that far away from true contention. Here are five steps that chief baseball officer Craig Breslow and the front office can take this offseason to make that leap.
1. Trade For Joe Ryan
The deal that the Red Sox — and no team in baseball — could pull off at the trade deadline should be the first move made this winter: Get Joe Ryan.
The 29-year-old turned in the best year of his career this season, going 13-10 with a 3.42 ERA over 171 innings, earning his first All-Star nod. In his career, he owns a 3.79 ERA, 1.063 WHIP, and 4.86 strikeout-to-walk ratio. Sliding him into a rotation with Garrett Crochet and Brayan Bello would be an upgrade over Lucas Giolito, who’s likely to opt out of the final year of his deal.
The Twins don’t have a direction at the moment, having just fired manager Rocco Baldelli coming off back-to-back fourth place finishes in the AL Central. Ryan is under team control through 2027, but the Twins won’t be competitive enough to make it worthwhile to keep him.
Meanwhile, the Red Sox have the pieces to get the deal done. Triston Casas, Jarren Duran, and Masataka Yoshida should all be on the trade block. And while Roman Anthony is untouchable, Breslow should apply some thought to trading either Marcelo Mayer (a perennial injury risk) or Kristian Campbell (a true unknown) if it means acquiring a solid No. 2 to sit behind Crochet for the next several years.
2. Re-Sign Alex Bregman
This one feels more like a necessity, if only because of the investment the team has already put into the three-time All-Star.
Bregman’s offensive numbers dipped in the second half (.927 OPS first half, .727 OPS second half), but he was clearly playing through the quad injury that kept him off the field for seven weeks this summer. Through it all, he provided steady defense while serving as a player-coach to many of his teammates. It’ll cost a truckload of cash, but the Red Sox have to keep him.
There’s little choice there, too, because of what the Bregman signing meant to the franchise. The signing late in spring training created the team’s issues with Rafael Devers, as Breslow and manager Alex Cora had to get Devers on board with moving to DH and then struggled mightily to get Devers to dust off his glove to play the field after injuries to Casas and then Bregman. Ultimately, it led to Devers being shipped away for peanuts, with the team deciding to take an addition-by-subtraction route.
That is to say: The Red Sox traded away the face of their franchise, and Bregman was a significant reason why it happened. Letting Bregman opt out and walk in free agency would be an organizational failure.
3. Sign Pete Alonso
The Red Sox need to fall out of love with Triston Casas.
The first baseman’s injury was used as something of an excuse to the Red Sox’ imperfections this season, but that lamenting often overlooked the reality that Casas was not playing well before getting hurt.
In 29 games, Casas was hitting just .182 with a dreadful .580 OPS. Most of that time was spent as the team’s cleanup hitter, a spot where he mustered a total of four extra-base hits in 53 plate appearances.
Casas’ injury did lead to the seemingly never-ending quest to find a first baseman. Abraham Toro, Romy Gonzalez and Nick Sogard were used before Nathaniel Lowe — having been DFA’d by the last-place Nationals — became available. Even Kristian Campbell and Masataka Yoshida donned first baseman’s mitts to try to get a feel for the position. It was a mess.
That’s why the Red Sox can’t mess around with the position this winter. All Pete Alonso will cost is money, and while everybody in baseball loves Kyle Schwarber, the Red Sox can’t be investing in a 33-year-old who can’t play the field.
Alonso, who will turn 31 in December, posted an .871 OPS this year, the second-highest mark of his career and the best since his Rookie of the Year season in 2019. Alonso is a beloved member of the Mets, but last year’s negotiations likely soured him on the team’s front office. At the very least, it provided a blunt reminder that the business of baseball can be brutal. That might have contributed to Alonso taking all of five seconds after the Mets were eliminated from postseason contention to announce that he’ll be opting out of his contract.
He’s due to get paid, but the market shouldn’t be anything that one of the richest franchises in baseball can’t fit into the budget.
4. Trade Jarren Duran and Masataka Yoshida
Whether it’s part of a Joe Ryan deal or in a trade to add depth somewhere on the roster, the Red Sox should say goodbye to both Jarren Duran and Masataka Yoshida this winter.
The latter was something that seemed impossible as recently as two months ago, as Yoshida’s contract has been an albatross on Boston’s books since he debuted in 2023. A light-hitting lefty who can’t play the field, Yoshida’s $18 million annual salary through 2027 was an unmovable contract. Yet after a strong September (.333/.351/.486 with two homers and 13 RBIs) and an effective postseason (4-for-7, two RBIs vs. the Yankees), Yoshida showed on the largest stage of his brief MLB career that he can provide some value to a team in need of a lefty bat. The Red Sox may need to eat some money on a Yoshida deal, but the lineup flexibility gained will make that worthwhile.
As for Duran — who butchered what should have been a simple catch in Game 2, contributing to the loss, while going 1-for-11 in his first postseason appearance — he simply appears to be the odd man out. Roman Anthony was arguably the team’s second-half MVP, Ceddanne Rafaela is an elite defender in center field, and Wilyer Abreu provides more useful pop in the lineup from the left side while being a superior defender to Duran. (Abreu is also still just 26, three years younger than Duran.)
Duran has his ups and downs, but he is at times an electric player. He’s sure to have a market around the league, and Breslow should be able to utilize that to improve his roster by clearing up that logjam.
5. Hope Aroldis Chapman and Garrett Whitlock can do it again
Arguably the most unbelievable part of the Red Sox season was the one-two punch that delivered a nearly perfect four-month stretch. Closer Aroldis Chapman had the single best season of his 16-year career, posting a minuscule 1.17 ERA and ridiculout 0.701 WHIP in his 67 outings. His 32 saves were his most since 2019, and the Red Sox almost had no choice but to extend the 37-year-old for another season (plus an option for 2027 that will kick in automatically if Chapman pitched 40 innings next year).
The question is, obviously, can he keep it up?
The Red Sox must believe so, even if a slight fall back to earth is to be expected from those otherworldly numbers.
They have to hope the same for setup man Garrett Whitlock, who — up until the the eighth inning of Game 2 — was likewise untouchable for the bulk of the season.
From June 29 until the end of the regular season, Whitlock posted a 0.56 ERA (two earned runs over 32 innings pitched) and 0.875 WHIP. That dominance, with Chapman often waiting in the wings, gave Cora the advantage of managing seven-inning games, knowing any lead was likely safe over the final two frames.
In that regard, the Red Sox needn’t do anything major on the back end of their bullpen. Even if there is a little bit of hope involved with a 38-year-old closer remaining dominant, Chapman is one of the most physically unique pitchers baseball has ever seen. And if he falters, Whitlock would seemingly be in position to pick up any necessary slack.