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Aroldis Chapman used to pitch for the Yankees.

There is some chatter across Major League Baseball that the Boston Red Sox could be headed towards selling this summer. There is still a lot of time to turn things around, but one name that’s surfaced in speculative talks and rumors is the ‘Cuban Missile’ Aroldis Chapman.

FanSided.com’s Christopher Kline recently predicted that Aroldis Chapman will be one of four Red Sox pitchers to get traded this summer:

“With Garrett Whitlock, Tyler Samaniego and other talented relievers ready to step into high-leverage situations, the Red Sox can trade Chapman without completely sacrificing their World Series aspirations in 2027 or beyond. This feels like the correct next step.”

So, should the Cubs target Aroldis Chapman via a trade? It worked out when they traded for Chapman in 2016, and eventually went on to win the World Series.

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Chicago Cubs Should Pursue Aroldis Chapman Again?

GettyBOSTON, MASSACHUSETTS – APRIL 17: Aroldis Chapman #44 of the Boston Red Sox pitches against the Detroit Tigers during the ninth inning at Fenway Park on April 17, 2026 in Boston, Massachusetts. (Photo by Brian Fluharty/Getty Images)

Look, there’s no telling at this moment if Boston actually wants to trade Aroldis Chapman, but the flamethrowing southpaw is still at the top of his game. He’s an 8X All-Star, likely headed to the Hall of Fame, and holds a 0.71 ERA this season.

He’s absolutely a player that the Cubs should pursue, given the injuries to their pitching staff and bullpen depth issues in the back end. Acquiring Chapman would put behind any doubts of who would come into the ninth inning to close games for Craig Counsell and company.

The point that Kline makes as reasoning for why Chapman might be dealt is due to recent massive trades revolving around closers in the last few seasons (Jhoan Duran, Mason Miller), so a Chapman trade can’t be ruled out, but the Red Sox would have to stay below the .500 mark.

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What Could the Cubs Give Up for Aroldis Chapman?

GettyCINCINNATI, OHIO – MARCH 26: Aroldis Chapman #44 and Carlos Narvaez #75 of the Boston Red Sox share a hug after the final out of the 3-0 win over the Cincinnati Reds on Opening Day at Great American Ball Park on March 26, 2026 in Cincinnati, Ohio. (Photo by Andy Lyons/Getty Images)

Back in 2016, when the Cubs originally acquired Chapman from the New York Yankees, it took four prospects to get a deal done. One of those players was Gleyber Torres, but the rest didn’t real pan out.

However, that trade kinda set the blueprint for what it might take to acquire Chapman again.

In this proposed trade, the Chicago Cubs send prospects Jonathan Long (No. 6) and Pedro Martinez (No. 8) to the Red Sox in exchange for their dominant closer.

Chapman also went on to win another World Series in 2023 with the Texas Rangers, but his career has been highlighted by an untouchable fastball that consistently sits around 102 MPH.

Most Cubs fans know him well from his time in the National League Central as well, but is he a name that Chicago should pursue when the months of June and July roll around?

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