Three key offseason questions after Yankees’ playoff loss to Blue Jays

NEW YORK — The New York Yankees’ offseason started earlier than they expected. They lasted a week in October before the Toronto Blue Jays eliminated them from the playoffs by winning Game 4 of the American League Division Series 5-2 and embarrassing them at Yankee Stadium with a wild on-field celebration.

For Yankees fans, there will be anger. There will be disappointment. Many may never accept that manager Aaron Boone’s club followed its 2024 World Series with such disappointment or that another historic year for Aaron Judge was wasted.

General manager Brian Cashman must have a short memory, however. Here are three of the biggest questions facing him this offseason.

What is Boone’s future?

The calls for Boone’s firing would have been much louder if they had lost to the Boston Red Sox in the Wild Card Series or been swept by the Blue Jays. Public pressure should be reduced on Boone. Expect the Yankees to treat this offseason like any other in recent history, looking back on their trade.

Of course, if there was a score for Boone’s career as Yankees manager, it would be 0 for 8. Zero ringers. Eight years. If the Yankees had known this would be the outcome before hiring Boone, they would have looked elsewhere. Or kept Joe Girardi.

But even with the Yankees’ early departure, there’s no indication Cashman is considering a change. On August 15, Cashman said Boone was “doing an incredible job of overcoming” the Yankees’ summer slump.

“I think it takes a certain character and ability to try to manage a group of 26 guys,” the general manager added, “especially in a big market, in tough times.”

Cashman thinks Boone has this character. Boone also seems to have the support of two huge voices: owner Hal Steinbrenner and superstar Aaron Judge, who have defended him at every turn. And although the Yankees disappointed for stretches this season, they finished 94-68, tied for the best record in the AL. Boone’s regular season winning percentage (.584) is second-best among active managers, trailing only Dave Roberts of the Los Angeles Dodgers (.621).

Boone has two years left on his contract. By the end, he will have spent 10 years as manager of the Yankees. Joe Torre and Girardi each spent 10 years at the position before Cashman made a change. In December 2020, Cashman said he hoped to have “10 more years with Boone.” Cashman seems likely to stay the course.

Which of their free agents will return?

The Yankees have eight unrestricted free agents: Paul Blackburn, Paul Goldschmidt, Trent Grisham, Amed Rosario, Austin Slater, Luke Weaver, Devin Williams and Ryan Yarbrough. They have two players who have a club option: Tim Hill ($3 million) and Jonathan Loáisiga ($5 million). Cody Bellinger has a $25 million player option that he will almost certainly decline to secure a long-term deal.

Goldschmidt will not be re-signed, as Ben Rice is the club’s future first baseman. Slater injured his hamstring and did not play after returning. He was left off the wild card list and the ALDS roster, and he probably won’t return. After rocky 2025 seasons for Weaver and Williams, signing both seems unlikely. The Yankees haven’t been signing relievers to expensive contracts lately. Yarbrough ended up being a quality signing as a depth option, but that’s all he is at this point in his career.

That leaves Rosario, Blackburn and Grisham as the three unrestricted free agents who could return in 2026. The Yankees have targeted Rosario in recent offseasons as a bench option. With Jose Caballero and a backup catcher (JC Escara?) locked in as two of the four bench options, maybe the Yankees will bring back Rosario. If Caballero and Rosario are on the roster in 2026, that could mean Oswaldo Cabrera doesn’t have a spot. This could mean he is traded or stashed in Triple A because both veterans are utility players like him.

There was some surprise two years ago when the Yankees re-signed Weaver after his brief tenure in 2023. It turned out to be a contract steal for the Yankees. Could Blackburn be that player this offseason? He had a good September, pitching 10 innings, allowing six hits and accumulating 14 strikeouts after the club made changes to its arsenal.

Grisham’s prospects this offseason are fascinating. He had a career year, hitting 34 home runs and posting a 129 wRC+. Among all main infielders this season, Grisham’s 129 wRC+ was second best. But there is a risk in giving Grisham, who will be 29 next season, a long-term contract. He’s never had a season like this, but his contact quality metrics suggest this production was no fluke, although his inability to hit against speed and break up pitches doesn’t help his case. His centerfield defense is overrated as he is one of the slowest players at that position. A further decline in his athleticism would force him to move to a corner of the outfield.

The Yankees could offer Grisham the qualifying offer, which would be a one-year, $22 million contract if he accepts it. If he declines and becomes a free agent, his market could be limited due to the penalties associated with signing a player with a QO attached. Grisham’s acceptance of the QO wouldn’t be the worst outcome for the Yankees, as it would give Spencer Jones, who was promoted to Triple A this season, more time to demonstrate whether he is a long-term option at the major league level. The same goes for Jasson Domínguez.

Hill’s option will likely be exercised; there is no reason for the club to part ways with him. The Yankees will almost certainly turn down Loáisiga’s contract after another injury-filled season.

Will the Yankees sign Bellinger or Tucker?

The biggest question for the Yankees this offseason is how aggressively they will attempt to improve their roster. Boone has repeatedly said this year’s team is the best he’s had in his eight seasons.

Bellinger has played a major role in the Yankees’ success this year, posting the highest fWAR (4.9) since his 2019 MVP season. Bellinger can play all three outfield positions, and his heavy-handed approach allows him to outperform his poor contact quality metrics. Bellinger, whose agent is Scott Boras, won’t settle for any team-friendly deal. But he will cost less than Tucker, the best free agent on the market.

Tucker had a bad season by his standards, and he still posted a 136 wRC+ for the Chicago Cubs. Playing half of his games at Yankee Stadium could help Tucker become a top-10 hitter in the sport. A key difference between the two players is their likely cost. Tucker could receive a contract worth $200 million more than Bellinger, which could mean Steinbrenner says Bellinger is a more acceptable option for his club.