Report: Chicago Cubs Eyeing Reunion With World Series Champion

The Chicago Cubs are rumored to be involved in the sweepstakes for Aroldis Chapman this summer. The Boston Red Sox have gotten out to a disappointing start to 2025. With Chapman possibly coming to the market, a guy who won a World Series with the Chicago Cubs almost a decade ago, they may be interested in a reunion with the hard-throwing lefty. Chapman, 37, is still pitching at a high level and would garner some interest if the Red Sox make him available at this year’s trade deadline.

The Chicago Cubs would be high on the list of teams to show interest in Chapman later this summer, especially with their lack of a true late-inning left-handed reliever. The team has relied heavily on Caleb Thielbar to bear the load of left-handed situations out of the bullpen. He has been adequate. Drew Pomeranz has also been sharp as of late, but Chapman would be a true step-up in class for the Chicago Cubs bullpen as they motor toward October. If they can bring him in, the Cubs have a much better chance of repeating what they did the last time they acquired Chapman. Win the World Series.

Chicago Cubs Monitoring Aroldis Chapman

The Chicago Cubs have emerged as one of the best teams in baseball in 2025, making this year’s MLB Trade Deadline a point of focus for the team if they want to make a deep playoff run. They have taken some steps already in 2025 to try and address one of the most pressing needs on their roster: left-handed bullpen help. They haven’t been able to effectively diversify their bullpen despite making minor transactions like trading for Tom Cosgrove and Drew Pomeranz and signing Genesis Cabrera. There is one move on the horizon though, that could go a long way in fixing that need.

According to Bob Nightengale, the Boston Red Sox could make hard-throwing lefty Aroldis Chapman available at the deadline if they fall out of contention in the AL playoff race. “Scouts already are keeping an eye on Boston Red Sox reliever Aroldis Chapman, who will be a hot commodity at the trade deadline if the Red Sox fall out of the AL East race,” he wrote.

If they entertain the idea of trading the 37-year-old Cuban hurler, Drew Vonscio says the Chicago Cubs are high on the list of teams that could be in line for his services. He wrote, “Chapman reuniting with the Cubs makes a lot of sense for both teams. If Chapman played for a true contender, he would have more saves this season than eight. The Cubs’ bullpen could certainly use another back-end member.”

World Series Reunion On the North Side

If the Chicago Cubs can acquire Chapman, it would be the second time they have made a deadline deal to bring him in. The first time that they brought him in, they went on to win the World Series in 2016, with Chapman being a critical part of their run. While Palencia has been hot lately as the closer, and Ryan Pressly has plenty of experience finishing ball games, Chapman would likely take over the closer role for the Chicago Cubs, as he did almost a decade ago.

Despite the time that has passed, Chapman is still a premier bullpen arm in MLB. So far in 2025 for Boston, Chapman has continued to throw the baseball at an elite level, going 3-2 with a 1.80 ERA, 0.96 WHIP, 33 strikeouts, and 9 saves in 25 innings across 27 appearances.

Chapman would infuse some much-needed help for Craig Counsell in the Chicago Cubs bullpen. The hard-throwing southpaw could alleviate some of the burden on Thielbar and provide another option late in games for a team that is expected to win their division and make a deep run into October.