Another season, another disappointment for the New York Yankees, who fell to the Toronto Blue Jays in a four-game ALDS. Now that the off-season is just around the corner, it is once again time to make tough decisions.
Paul Goldschmidt, Luke Weaver, Devin Williams, Trent Grisham, Ryan Yarbrough, Paul Blackburn and Amed Rosario will all be free agents. Cody Bellinger is expected to opt out of his contract, and Jonathan Loaisiga has a club option.
With numerous players set to hit free agency, general manager Brian Cashman will be tasked with deciding which of the Yankees’ potential departures have earned another shot with the team and which have not. While there’s something to be said for each of their headliners in the free agent class, there’s one high-profile player the Yankees should definitely look to reunite with, and another they’ll almost certainly have to let go.
Bringing back: Devin Williams
It may be controversial, but how many chances does a team get to sign an elite closer at a rock-bottom price? If there’s one thing that’s consistent about relievers, it’s inconsistency. Even elite closers like Edwin Diaz and Josh Hader each had one season with an ERA above 5.00.
In Williams’ case, it was a 4.79 ERA in his lone year as a Yankee. But as the year came to an end, he returned to his usual air-bending form. In the playoffs, Williams pitched four scoreless innings in four appearances, the first postseason in which he posted an ERA under 21.60. Furthermore, his 90 strikeouts in 62 innings this season are a reminder that his dazzling talent has not diminished.
Because his regular season went poorly, Williams’ price in free agency will come with a significant price cut, making this a gamble with limited downside and explosive upside. Given his potential, his low price, and the Yankees’ ongoing bullpen woes, Williams might not be a bad bet. Williams will likely pursue a short-term deal (likely with New York) to increase his value before testing the market again.
Don’t Chase: Trent Grisham
Grisham wasn’t exactly a high-profile player until this season. He posted a career year with a .235/.348/.464 slash line and a career-high 34 home runs, surpassing his previous career-high of 17. His success this season has undoubtedly increased his once insignificant price.
Overall, he made a significant impact with the Yankees in 2025, but it comes with some suboptimal stats. In the regular season, Grisham struck out 137 times in 494 at-bats, following a career-long pattern of high strikeouts combined with low batting averages. He made up for it by drawing a walk, but in the postseason his tendency to strike out got the better of him and he recorded 10 in 29 at-bats. Grisham hit a paltry .138/.219/.207 with no home runs in the 2025 playoffs, contributing to the Yankees’ demise while batting from the leadoff spot.
Additionally, Grisham saw a sharp decline in his defensive stats. The two-time Gold Glover posted -1 out above average fallen dramatically this year from its peak of 16 in 2022.
Aside from his atrocious playoff performance, declining defensive stats and high strikeout rates, there is also a chance that Grisham will regress. His average annual slash line is .218/.321/.400 with a 162-game average of 22 home runs. Over the past two seasons, he has posted batting averages in the .190s. Whether this year was a flash in the pan or the start of a new upward trend in his performance, Grisham is probably not a risk the Yankees should take given his high price tag.
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