There are some Yankees exits that barely register, and then there are the ones fans practically celebrate. When a player has spent enough time irritating the fan base - whether through rough stretches on the field or just an all-around maddening presence - free agency can feel less like a loss and more like a cleanup job.
That’s the lane Jazz Chisholm Jr. appears to be heading toward. A lot of Yankees fans will be more than happy to move on from the mid-game lollipop routine and whatever else came with the package.
The talent was real at times. On his best days, he looked like one of the better second basemen in baseball.
But the lows hit hard enough to drown out the highs.
He’s hardly the only one.
Mark Leiter Jr. was once one of Aaron Boone’s most trusted bullpen options after arriving from the Chicago Cubs in 2024, but his Yankees run was a roller coaster. There were nights when he looked untouchable, piling up strikeouts and breezing through innings.
Then there were the outings that looked like batting practice. His Yankees line - a 4.89 ERA and 1.586 WHIP in 80 games - made it easy for fans to accept the goodbye.
Devin Williams followed a similar script, only with even more whiplash. He missed bats at an elite clip, finishing 2025 with a 13.06 strikeout per nine rate in 62 innings.
But he also gave up 33 runs, which is the kind of damage that wipes out all the good stuff in a hurry. For context, he allowed just 48 earned runs in 235 2.3 innings for the Milwaukee Brewers across his first six seasons combined.
The collapse in New York was staggering.
Gleyber Torres is a tougher one, because his early Yankees days were genuinely exciting. In 2019, he blasted 38 homers, drove in 90 runs and posted a 129 OPS+ season that had him looking like a future Monument Park type.
Then came the post-COVID slide, and he was never quite the same. The bat cooled off, the defense drew more attention, and the base-running mistakes only made things worse.
When he left for the Detroit Tigers in free agency, there wasn’t much heartbreak in the Bronx.
Alex Verdugo never really gave Yankees fans a signature moment to hold onto. Sure, he made a spectacular ninth-inning catch in Game 1 of the 2024 World Series against the Los Angeles Dodgers, but that memory got swallowed up by Freddie Freeman’s walk-off grand slam.
Beyond that, there wasn’t much to point to. His .647 OPS in 2024 and those frustrating rollover grounders to second base told the story well enough.
When he hit free agency, nobody was lining up to bring him back - and the Yankees had already done the Red Sox a favor by taking him in the first place.
Frankie Montas belongs in the same category, only for a different reason: he barely got on the field. Acquired from the then-Oakland A’s in 2022 with a shoulder injury already in tow, he appeared in just nine games over two seasons.
The results weren’t much better than the availability. He posted a 6.15 ERA and 4.90 FIP in 41 innings.
Once he reached free agency after the 2023 season, his departure also opened the door for Luis Gil to rejoin the starting rotation.
Isiah Kiner-Falefa’s Yankees tenure might have looked different if he had spent all of it as a utility piece. Instead, he was the starting shortstop in 2022, and that’s where the frustration really set in.
The defense was shaky, the errors were costly, and there wasn’t enough offense to cover for any of it. In the Bronx, there was nowhere to hide.
His exit felt overdue.
Domingo Germán is another name many fans were ready to be done with long before he actually left. After his 81-game suspension from Major League Baseball in January 2020 for violating the league's Joint Domestic Violence, Sexual Assault and Child Abuse Policy, plenty of people hoped that would be the end of the story.
The Yankees kept him around anyway. Even his perfect game against the A’s in June 2023 came with a strange, uneasy feeling attached to it.
When he finally reached free agency after that season, it felt like it came a few years late.
And then there was Andrew Heaney, whose Yankees stint can be summed up in one brutal stat: 13 home runs allowed in 35 2/3 innings after arriving from the Los Angeles Angels in 2021. That’s a homer every three innings, which is the kind of number that makes a pitching staff wince. He later found success with the Texas Rangers and Dodgers, but Yankees fans weren’t losing sleep over his turnaround.
In Other News...
Yankees Face A Massive Gunnar Henderson Decision With Their Future At Stake
The idea of the Yankees making a run at Gunnar Henderson has become one of the more intriguing possibilities on the board, and it makes sense why. He is already performing like a centerpiece, and with contract control through 2028, he would give New York the kind of long-term answer at shortstop that teams spend years trying to find. For a club that always has to weigh present urgency against future planning, Henderson checks a lot of boxes at once.
The catch is the price. A deal with Baltimore would likely require the Yankees to part with multiple top prospects, which is exactly the kind of move that can reshape a farm system in a hurry. The Orioles have shown a willingness to listen on trades, though not when it comes to first baseman Pete Alonso, and that only sharpens the focus on how aggressive New York wants to be. For the Yankees, the real question is whether adding Henderson now is worth the kind of prospect loss that could echo for years. [Read more 🡒]
Yankees Suddenly Have A Real Shot At An Infield Upgrade
The Yankees are at least worth watching here, because Oaklands willingness to listen on Jacob Wilson opens a door that did not seem especially wide a short time ago. The Athletics are looking to strengthen their starting pitching, and that is the kind of need New York can potentially help address if it decides to get aggressive with its pitching inventory.
Wilson is not being shopped in a rush, and the As have made clear they do not have to move him. Still, the fact that they would consider offers gives the Yankees a possible path to an infield upgrade if the right package comes together, even if nothing has been finalized and the talks remain in the early stages. [Read more 🡒]
Yankees May Have Found Their Ryan McMahon Escape Plan
The Yankees have spent the offseason looking for a cleaner answer at third base after the position fell short in 2026, and one name now sitting on their radar is Teruaki Sato. The Hanshin Tigers slugger just won the Triple Crown in Japans Nippon Professional Baseball and has been posted, putting him on the market at a time when New York is clearly searching for more impact on the left side of the infield.
Sato is not going to come quietly, though, because the Yankees are hardly alone in chasing him. Still, the fit is obvious enough to keep watching: if New York can land a bat of that caliber, it could reshape how the club handles Ryan McMahon, whose grip on an everyday role is far from certain as the Yankees weigh their next move at third. [Read more 🡒]