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For the first time in 15 years, the New York Yankees reached the World Series in 2024, though they remain titleless since 2009. They were defeated in five games by the Los Angeles Dodgers and, frankly, they gave away Game 5 with a comedy of errors. It was the sort of ugly, embarrassing loss that sticks with you throughout the offseason, if not longer.

"We had a struggle with our baserunning this year. We were a bad defensive team, without a doubt, at times this year," general manager Brian Cashman said at the GM Meetings last week (via MLB.com). "But we also, when you add it all together, we were a really good baseball team that earned the right to win the American League, and get all the way to the World Series."

The Yankees will now spend the winter trying to build a team good enough to not only get back to the World Series, but also win it. They've already handled one important piece of offseason business: Gerrit Cole will return on his four-year, $144 million option. The Yankees didn't have to give him an extension either. Cole is returning under the terms of his original contract. It's like nothing ever happened.

With the Cole question already answered, let's now break down what the Yankees are up against this offseason.

Key free agents

Soto, the offseason's clear-cut No. 1 free agent, is the headliner here, though the Yankees could also potentially lose their second baseman/leadoff hitter (Torres) and top three setup relievers (Hill, Holmes, Kahnle) to free agency. They will of course make a run at re-signing Soto, and I suspect the rest of their offseason will be on hold until Soto makes his decision.

"We certainly have an interest in retaining him and we'll put our best foot forward there," Cashman said about Soto (via the Associated Press). "That will either lead to us retaining him and signing him back, or we'll be forced to go to a different direction if we can't. And if we can't, there's a lot of different players in this marketplace that can positively impact this roster in different ways."

Biggest needs

The Yankees need two middle of the order bats this offseason. They would love Soto to be one, and, even if they do retain him, they need another No. 5-6 type hitter, with first base an obvious spot to add one. The Yankees declined Anthony Rizzo's club option two weeks ago and they received a .216/.284/.335 line from their first basemen in 2024. It shouldn't be hard to upgrade on that.

It's possible the Yankees will go internal at second base -- Cashman mentioned prospect Caleb Durbin as a second base candidate at the GM Meetings -- and maybe in left field too, where top prospect Jasson Domínguez is more or less ready to take over. Owner Hal Steinbrenner has indicated payroll will come down in 2025. Second base and left field are places to possibly save money.

The Yankees are very good at building bullpens on the cheap -- 2024 revelation Luke Weaver will be back next year after his $2.5 million option was picked up -- and I would be surprised if they spent big on, say, free agent Jeff Hoffman or Devin Williams via trade. It's not impossible. Just unlikely, I think. Keep an eye out for a Hill reunion. He was a great fit and won't be expensive.

On paper, the Yankees have six starters for five rotation spots (Cole, Nestor Cortes, Luis Gil, Carlos Rodón, Clarke Schmidt, Marcus Stroman), though don't be shocked if they look to add a starter. Cole and Schmidt missed significant time with injuries in 2024. Cortes had a flexor strain late in the year. Rodón has a lengthy injury history. Gil set a new career high in innings (by a lot).

The Yankees lost the World Series but their pitchers still endured that huge workload, and they have one fewer month to recover in the offseason. Six starters for five spots is nice in theory, but there's injury risk in that rotation. Injury risk that is heightened by the team's deep postseason run and shorter than usual offseason. I bet the Yankees get connected to starters soon enough.

At this stage of the offseason, New York's priority list looks something like this:

  1. Re-sign Soto
  2. Big first base bat
  3. Rebuild the bullpen
  4. Reinforce the rotation
  5. Figure out second base
  6. Figure out the other outfield spot
  7. General depth

Cot's Baseball Contracts estimates New York's 2025 competitive balance tax payroll at $238.8 million. They had close to a $320 million payroll for CBT purposes in 2024. Reducing payroll to, say, $300 million next year would leave the Yankees with about $70 million to spend this winter, most of which they want to give to Soto. It won't leave much to do everything else.

If the Yankees succeed in re-signing Soto, the rest of their offseason could be low-key despite a fairly long shopping list. If they miss out on Soto, then perhaps they'll pivot and sign two or three top free agents (Pete Alonso? Alex Bregman?) and try to replace Soto in the aggregate, which is the sorta thing that should be reserved for small payroll teams, not the Yankees. But I digress.

Possible fits

It's hard to say how active the Yankees will be this offseason without knowing Soto's status. He is, obviously, the No. 1 target on their board and they'll do what they can to bring him back. New York's team-building approach will look very, very different with and without Soto. Here are a few possible offseason targets with the caveat that Soto's decision could change everything.

SP Garrett Crochet, Chicago White Sox: It is a matter of when the ChiSox will trade Crochet, not if. He pitched at something close to an ace level in 2024 and has two years of control remaining. After losing the World Series, the Yankees could push all their chips in next year, and trade for one of the game's top lefties. All indications are Domínguez is not untouchable. The Yankees won't give him away, but for a guy like Crochet, I assume he's on the table.

2B Brandon Lowe, Tampa Bay Rays: The Rays trade their most expensive players every offseason like clockwork and Lowe's $10.5 million 2025 salary is currently the highest on the roster. He's played first base in addition to second, and his lefty pull power would fit perfectly with Yankee Stadium's short right field porch. Intradivision trades are always tricky. Tricky does not mean impossible though. Could these two AL East rivals hook up for a Lowe trade this winter?

RP Tanner Scott, free agent: The Yankees are not shy about paying a reliever big money (they had Zack Britton and Aroldis Chapman both making eight figures at the same time), though they haven't done it in a few years now. Perhaps that will change this winter. The biggest problem with New York's 2024 bullpen was a lack of swing and miss. Their bullpen finished middle of the pack in strikeout rate and Scott would fix that right up. He could step into the closer's role and free up Weaver for fireman work.

SP Tomoyuki Sugano, free agent: Sugano, 35, has been the generation's best starting pitcher in Japan, and he's looking to make the jump to MLB as a true free agent this winter (i.e. no posting process). He's spent his career with the Yomiuri Giants, who are the Yankees of Japan given their history. The Yankees have a history of courting productive Japanese veterans (Hideki Matsui, Masahiro Tanaka, etc.) and could make a run at Sugano, who's drawn comparisons to former Yankee Hiroki Kuroda.

1B Christian Walker, free agent: Alonso is New York battle-tested and very productive, but Walker is the better all-around player, and it was painfully obvious in the postseason that the Yankees need to upgrade their defense. Walker brings 30-homer pop and arguably the game's best first-base glove. Also, he turns 34 in March, and that means his contract will be fairly short. Alonso's several years younger and the bigger name, but Walker figures to be the better bang for your buck.