With the New York Yankees looking to improve their bullpen before the trade deadline, a surprising and familiar name has often been linked to them.
The Bronx Bombers' hated rivals, the Boston Red Sox, have one of the most coveted relievers available if they choose to sell. That is veteran left-handed closer Aroldis Chapman, who has turned back the clock since 2025 to become one of MLB's best relievers once again.
While Chapman pitched with the Yankees for two separate stints, first in 2016 and then from 2017 to 2022, his time in the Bronx ended bitterly. The 38-year-old flamethrower later said that he would retire rather than pitch for them again.
Chapman's stance seems to have softened in a recent interview with Enrique Rojas of ESPN, but he still has a demand to feel comfortable pitching in pinstripes again.
"What happened, happened," Chapman said to Rojas. "If something like this were to happen, I believe someone from this organization should apologize first."
Chapman confirmed that "someone" was current Yankees general manager Brian Cashman.
The "Cuban Missile" lost his closer job to then-Yankee right-hander Clay Holmes in 2022 and later finished that season with a bloated 4.46 ERA and 4.57 FIP. Before the Yankees began their postseason run, Chapman missed a mandatory team practice; although the southpaw claims he had permission from the team to go down to Miami, GM Cashman instead left him off New York's postseason roster.
Why the Chances of Aroldis Chapman Rejoining the Yankees are Nonexistent
Chapman's comments imply that there could be a scenario where the Red Sox trade him to the Yankees at the deadline. However, in reality that is an extremely unrealistic circumstance.
Most notably, the Yankees and Red Sox hold arguably the fiercest rivalry in professional sports, and as such they rarely trade with one another. There are exceptions like the Alex Verdugo trade in 2024 and, more recently, a trade that sent catcher Carlos Narvaez to Boston for pitching prospect Elmer Rodriguez. But in a scenario where the Red Sox would help out the Yankees by trading them a top reliever in the majors, they would never even consider making such a move.
Another reason is that animosity is on both sides. Chapman has made his disdain for the Yankees' organization extremely clear for how they allegedly treated him, but the organization likely considers Chapman more trouble than he is worth.
The Yankees initially got Chapman from the Cincinnati Reds at a reduced prospect price due to domestic violence charges; that personal conduct violation during the offseason resulted in a 30-game suspension to begin the 2016 season. Additionally, the 2022 season saw Chapman land on the injured list with an infection he developed when getting a tattoo, which drew the ire of the Yankees' higher-ups along with his poor individual season.
And of course, Chapman had three crucial postseason failures in the Bronx. He gave up a walk-off double to Carlos Correa in Game 2 of the 2017 ALCS against the Houston Astros and a game-winning home run to Mike Brosseau of the Tampa Bay Rays in the decisive Game 5 of the 2020 ALDS; Chapman had thrown a pitch at Brosseau's head during a regular season meeting that year that earned him a suspension. Above those, though, is the walk-off home run to Jose Altuve in Game 6 of the 2019 ALCS that clinched the American League pennant for the Astros. Chapman's wry smile upon giving up the home run has since gained notoriety online.
All of this creates a near-impossibility of Chapman returning to the Yankees. The Red Sox would never entertain a trade that benefits their most hated rival, Chapman has yet to forgive the Yankees for their treatment of him, and the Yankees have yet to forgive Chapman for his off-field issues and the big hits he allowed in the postseason.
As it stands, Chapman has a microscopic 0.46 ERA and 1.99 FIP in 20 appearances this year, nailing down 13 saves in the process. If Boston chooses to sell high on him, there will be a multitude of suitors - but the Yankees won't be one of them.
