Aroldis Chapman’s 14 saves from 23 games this season amid the Boston Red Sox’s disappointing run have naturally created some buzz around him before the trade deadline. And the New York Yankees are looking to boost their bullpen for a deep October run. On paper, this looks like a perfect match. But one baseball insider said their bad history will stop a deal.

“When you didn’t win the World Championship in 22, and when you look back at what he did to the team. I think that stays with you for a while,” analyst Jim Bowden explained. “There’s some bad blood [between the two] there that’s hard to take away.”

The Yankees are leading the AL East with a 47-31 record and already preparing themselves for the postseason. But before they complete the regular season, they are looking for reliable bullpen arms to overcome their World Series drought since 2009. To do this, they need strong relief pitchers to help their starters rest. And Chapman appears to be one of the best candidates. 

New York’s key relievers are not at their best. Camilo Doval is struggling with a 5.22 ERA over 29.1 innings. Tim Hill was doing great earlier in the season, but his June numbers are worse than Doval’s. He transitioned from 1.93 in April to 5.40 this month. And Jake Bird recorded a 4.88 ERA before he was optioned to Triple-A. The Yankees’ new three-headed monster, Fernando Cruz, Brent Headrick, and David Bednar, has done quite well in June. But a stronger bullpen is necessary for the playoffs, and the franchise wants to properly manage the workload of the starters as well. 

Chapman has a 2.08 ERA with 29 strikeouts and 14 saves this season. He is exactly the type the pinstripes are looking for. But their past makes a trade almost impossible. Chapman was one of the original three-headed monsters alongside Andrew Miller and Dellin Betances in their 2016 roster. He spent a long time with the Yankees before their relationship soured in 2022.

Bowden highlighted how Chapman got a tattoo that resulted in a leg infection, sidelining him for a month in the middle of a pennant race in that season. Later that season, he skipped a required team workout and flew to Miami. The Yankees were very angry and kicked him off their playoff team.

Chapman believes that the franchise and its baseball executive, Brian Cashman, should apologize to him. However, manager Aaron Boone clearly said that the team doesn’t owe him any. 

Given the impasse, a trade between the Red Sox and the Yankees involving Aroldis Chapman is highly unlikely. While Bowden acknowledged that Chapman has matured, he believes that the bridge has been burned. But the reliever might still not end the season in Boston.

Why the Red Sox could move Chapman

Boston has been stuck at the bottom of the AL East almost the entire season. And there are hardly any chances of a quick change in their position. And Chapman is one of the bright spots on the roster. Even Bowden believes him to be one of the best relievers in MLB right now. 

And as his value increases, so do the chances of his trade. 

He is on a 1-year, $13.3 million contract with the Red Sox. There’s a clause in the deal that says, if Chapman pitches 40 innings this season and passes the physical at the end, the contract automatically extends at a $13 million rate for 2027. 

He has already pitched 21.2 innings this season. But the franchise doesn’t consider the amount justifiable for someone who turns 39 next February. Instead, the Red Sox can gain some financial flexibility if they trade him away this summer. Boston can focus more on rebuilding for the next season. 

All these indicate a likely move for Aroldis Chapman. But analyst Jim Bowden has made it clear that his reunion with the Yankees is not on the cards.