Remembering the most satisfying Yankees free agent departures over the last few years

There are just certain players who have an impressive ability to get under fans' skin. Whether it’s because of their frustrating performance on the field or questionable behavior off of it, they can make it pretty difficult for you to cheer for them. As a result, their departures from your favorite team can sometimes be a welcome sight. This includes a number of high-profile New York Yankees players in recent years.

With the very likely departure of Jazz Chisholm Jr., a large portion of Yankees fans will breathe a sigh of relief over never having to think about a mid-game lollipop again. As a ballplayer, he certainly had his fair share of highs. When he was on, he was one of the best second basemen in the league. However, his lows overshadowed the positives and made watching him play a frustrating experience at times.

These former Yankees couldn’t have left town soon enough via free agency

Chisholm Jr. is not alone, though. Over the last few years, a growing collection of players made some Yankees fans leap for joy when their contracts expired and they departed once the offseason began. We’re not talking about the Juan Soto’s of the world who left to chase the bag. We’re looking for those players who never stood a chance of playing in the Bronx again.

Mark Leiter Jr., RP

Once upon a time, Mark Leiter Jr. was one of Yankees manager Aaron Boone’s most-trusted arms out of the bullpen. After being acquired from the Chicago Cubs in 2024, Leiter Jr. was something of a wild card for the Yankees throughout his tenure. He had his stretches of pure dominance, racking up the strikeouts and pitching clean innings. He also had his games where he looked like he was tossing batting practice. With a career 4.89 ERA and 1.586 WHIP in 80 games with the Yankees, you can bet that fans weren’t too upset about Leiter Jr. moving on.

Devin Williams, RP

Devin Williams had a very similar up-and-down time with the Yankees as Leiter Jr. The biggest difference is that Williams was still absolutely filthy when he was in the middle of a meltdown. He was truly a complete enigma. With a 13.06 strikeout per nine rate in 62 innings in 2025, Williams was among the best in baseball at striking out batters. The problem is that he also surrendered 33 runs. To put things into perspective, he coughed up just 48 earned runs in 235 2.3 innings for the Milwaukee Brewers in his first six seasons combined. It’s almost impressive how quickly things went south for Williams with the Yankees.

Gleyber Torres, 2B

This one is tough, because through his first two seasons with the Yankees, Gleyber Torres appeared as if he was on the fast track to Monument Park. In 2019, he hit 38 homers and drove in 90 runs on his way to a 129 OPS+ season. But following the COVID-19 shortened season, he was never the same player. He often struggled mightily to find the same level of success at the plate. That only magnified his occasional lackadaisical play in the field and questionable choices on the base paths. It was sad to see a player regress after showing such promise early on, but when he left for the Detroit Tigers in free agency, Yankees fans didn’t exactly shed a tear.

Alex Verdugo, OF

Unlike most other players on this list, Alex Verdugo never seemed to have an iconic moment as a Yankee. He made a spectacular ninth-inning catch during Game 1 of the 2024 World Series against the Los Angeles Dodgers, but nobody remembers that play after Freddie Freeman’s walk-off grand slam. Because of that erasure, it would be hard to point to any one thing he ever did well as a Yankees player. His propensity for frustrating rollover groundouts to second base best explains his .647 OPS in 2024. When he became a free agent after the season, there weren’t any calls for his return. The worst part of all is that we took this problem off the Red Sox's hand via trade.

Frankie Montas, SP

Okay, make that two players who lacked any iconic moment for the Yankees. But that’s because Frankie Montas simply never really played enough for the club to have any. After being acquired from the then-Oakland A’s in 2022 (knowing he had a shoulder injury!), Montas appeared in just nine games for the Yankees in two seasons. Those nine games weren’t particularly good either. Montas had a 6.15 ERA and 4.90 FIP in 41 innings for the Yankees. After entering free agency at the end of the 2023 season, Montas’ departure helped free up space for Luis Gil to rejoin the starting rotation.

Isiah Kiner-Falefa, UTL

If Isiah Kiner-Falefa spent his entire Yankees career as a utility player, fans just might remember his time with the team a little differently. However, as the Yankees’ starting shortstop for the 2022 season, he drew the ire of fans for his questionable defense and costly errors. Without a plus bat to make up for his deficiencies in the field, there wasn’t anywhere for Kiner-Falefa to hide in the Bronx. Maybe in another universe he’s a beloved fan-favorite Yankees player, but in our reality, his departure couldn't have come faster.

Domingo Germán, SP

After Domingo Germán received an 81-game suspension from Major League Baseball in January 2020 for violating the league's Joint Domestic Violence, Sexual Assault and Child Abuse Policy, many fans hoped that would be the last time that they had to hear from him. Instead, the Yankees kept Germán around. But even after he hurled a perfect game against the A’s in June 2023, it felt like a dark cloud hanging over what should have been a joyous occasion. When Germán left for free agency following the season, it felt like a few years too late.

Andrew Heaney, P

To end on a lighter note, Andrew Heaney was just a classic case of a pitcher forgetting that their job is to prevent the opposing team from scoring runs. After being acquired from the Los Angeles Angels in 2021, Heaney put up one of the worst seasons from a Yankees pitcher in a very long time. In 35 2/3 innings pitched, he allowed 13 home runs. That’s good for a long ball every three innings. A pitching machine would have a harder time surrendering that many home runs. Heaney would eventually find success with the Texas Rangers and Dodgers over his next few seasons, but Yankees fans weren’t too upset over that.

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