Are the Cubs eyeing a reunion with a key member of the 2016 World Series team?

The 2016 Chicago Cubs had many heroes on their team en route to a historic World Series Championship. The Cubs had Kris Bryant, who took home the National League MVP award to go along with a pair of Cy Young finalists in Kyle Hendricks and Jon Lester. However, no player was more important down the stretch than closer Aroldis Chapman. 

Acquired at the 2016 MLB trade deadline, Chapman was dominant in his brief stint in Chicago, racking up 16 saves with 46 strikeouts in 26 2/3 innings of work. In the postseason, he became manager Joe Maddon’s most trusted arm, appearing in 13 games throughout the playoffs, picking up four saves in the process. 

Chapman returned to the New York Yankees in free agency after the 2016 season, closing the book on Chapman’s time with the Cubs.

Now, a reunion may be in the cards with the hard-throwing left-hander

As it stands, the Boston Red Sox sit in fourth in the AL East with a record of 29-32. Should they look poised to miss the playoffs, Bob Nightengale of USA Today reports that the Red Sox would be inclined to listen to offers on the 37-year-old reliever.

MLB insider Mike Rodriguez took things a step further, saying that if the Cubs remained in the pennant race ahead of the deadline, they would become one of the frontrunners to land Chapman.

While no longer the dominant closer he used to be, Chapman still poses as a viable option in the back end of a Major League bullpen. In 2025, Chapman is 8-for-9 in save situations while striking out 31 batters in 23 innings, coupled with only eight walks. His trademark fastball is still more than intact, as he ranks in the 98th percentile of MLB with an average velocity of 99.2 MPH.

Chapman would be a welcome addition in the Cubs’ bullpen, with their main lefty options being Drew Pomeranz, Caleb Thielbar and the newly acquired Genesis Cabrera. More importantly, a reunion would certainly be cheaper this time around, as the original trade package in 2016 cost the Cubs their then-top prospect in Gleyber Torres, who went on to be a two-time All-Star with the Yankees.

The Cubs find themselves in a very similar situation as they were in 2016, currently possessing the best record in the National League in the midst of a playoff push. A trade for Chapman may give them the extra boost they need to make a deep run, just as it did nearly 10 years ago.