Two high-profile moves Yankees need to make in free agency

Another season, another disappointment for the New York Yankees, who fell in a four-game ALDS to the Toronto Blue Jays. With the offseason ahead, it’s time again 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 enter free agency, general manager Brian Cashman will be tasked with deciding which of the Yankees' potential departures earned another shot with the team and which haven’t. While there is a case to be made for each of their free agent class headliners, there is one high-profile player the Yankees should definitely seek a reunion with and another they should almost certainly let go.

Bring 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 is one thing consistent about relievers, it’s inconsistency. Even elite closers such as 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 only year as a Yankee. But as the year came to a close, 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 below 21.60. Plus, his 90 strikeouts in 62 innings pitched this season serve as a reminder that his staggering talent hasn’t diminished.

Since his regular season went poorly, Williams’ price in free agency will come with a significant markdown, making this a gamble with limited downside and explosive upside. Given his potential, discounted price and the Yankees’ continuous bullpen problems, Williams might not be a bad bet. Williams will likely pursue a short-term deal (likely with New York) to boost his value before testing the market once more.

Do not pursue: Trent Grisham 

Grisham wasn’t exactly a high-profile player until this season, posting a career year with a .235/.348/.464 slash line and a career-high 34 home runs, trouncing his previous career high of 17. His success this season has undoubtedly raised his once-insignificant price.

Overall, he made a sizable impact with the Yankees in 2025, but this comes with some sub-optimal stats. In the regular season, Grisham struck out 137 times in 494 at-bats, following a career-long pattern of posting high strikeout rates paired with low batting averages. He made up for it by drawing walks, but in the postseason, his tendency to strike out got the better of him, garnering 10 in 29 at-bats. Grisham hit a meager .138/.219/.207 with no home runs in the 2025 playoffs, contributing to the Yankees’ downfall while batting from the leadoff spot.

In addition, Grisham saw a steep decline in his defensive metrics. The two-time Gold Glove winner posted -1 outs above average this year, down drastically from his peak of 16 in 2022.

Aside from his ghastly playoff performance, declining defensive stats and high strikeout rates, there is also the chance Grisham could regress. His average annual slash line is .218/.321/.400 with a 162-game average of 22 home runs. His past two seasons saw him post batting averages in the .190s. Whether this year was a flash in the pan or the start of a new upwards trend in his performance, Grisham probably isn’t the risk the Yankees should take, given his elevated price tag.