Building a Trade That Brings A Former World Series Champion Back to Chicago

After struggling in a mighty way in the early part of the season, the Chicago Cubs bullpen has stepped up and become one of the best in baseball over the last month. They have put up excellent numbers despite losing Porter Hodge for a period and have gotten contributions from unexpected arms such as Brad Keller, Drew Pomeranz and Chris Flexen. It has been a sigh of relief most nights to know that the bullpen is more than likely going to do its job and help the Cubs get a win.

While the success has been a welcome sight, it is safe to assume that the unexpected production from the previously mentioned players will not hold up throughout the entirety of the season (or, at least, not all of them will hold up this level of production). Because of that, Chicago may be exploring trades for pitching when the trade deadline rolls around. One pitcher that may become available if his team continues to struggle is left-hander and former World Series champion Aroldis Chapman.

Chapman is highly remembered as one of the heroes of the 2016 World Series team, and for the most part, that is correct. We all remember the home run allowed to Rajai Davis in Game 7 of the World Series, but he returned for one of the most gutsy ninth innings ever pitched, so it's easy to forgive an overworked Chapman for that blip. A reunion with the Cubs could make the bullpen even more dangerous and add another power left-handed arm to pitch in high leverage situations.

Chapman is having an excellent season with the Boston Red Sox, posting a 1.80 ERA, nine saves and 33 strikeouts in 27 appearances and 25 innings pitched, He's posted an ERA under 3.80 in each of the last two seasons and is well on his way to doing so again in 2025. With the Red Sox going downhill fast (30-34, fourth place in the AL East) and Chapman being on a one-year deal, he is a prime trade candidate.

Now, we need to acknowledge that Chapman is both an old (37) rental and not the best human being off the field. Cubs fandom went through all these emotions when the team first acquired him back in 2016, so we won't rehash everything here, but it's a not-insignificant-part of Chapman's legacy that he was suspended for domestic violence back in 2016.

Looking beyond that and focusing purely on the baseball fit, there's a reason why Chapman will be highly sought-after at this upcoming trade deadline. This is just one of many possible packages the Cubs could offer to secure the flamethrowing southpaw's services.

Cubs receive: LHP Aroldis Chapman

Red Sox receive: RHP Jack Neely (CHC No. 16 prospect) and SS/3B Yahil Melendez (CHC No. 24 prospect)

Chicago gets its high-leverage left-handed arm and the return to Boston gives them a young, controllable pitching prospect in Neely and an infield prospect of Melendez that will likely be blocked through the system because of the high amount of middle infield talent Chicago has (which is a problem the Red Sox are also dealing with, which could encourage them to seek out a secondary pitching prospect instead). Because Chapman is on just a one-year deal, the Cubs could likely get away with not giving up a top-15 prospect within the organization. 

If the Cubs are able to strike a deal for Chapman, it would be hard to not consider the back-end trio of Hodge, Chapman and Palencia as one of the best in the entire league. A hard-throwing, lockdown arm from the left side could be exactly what Chicago needs to win the NL Central and get back to the postseason for the first time since 2020.