After the bullpen struggled in their opening four-game series against the Arizona Diamondbacks, the Chicago Cubs could be in the market for bullpen help very early on in the season.
One thing Chicago does not have very much in the bullpen is left-handed pitching. Caleb Thielbar is the lone lefty down in the bullpen for the Cubs and that will be a tough way to get through the season.
With not a ton of left-handed relief talent on the market, here is a potential trade Chicago could try to pull off to get another left-handed arm.
Cubs receive: LHP Garrett Cleavinger
Rays receive: RHP: Javier Assad and SS/3B Yahil Melendez (CHC No. 24 prospect)
These two teams are no strangers to making a trade as just last season, Chicago acquired 3B Isaac Paredes in exchange for 3B Christopher Morel and RHP Hunter Bigge. This trade would be almost identical with a 3B and pitcher going back to Tamp Bay in return for the lefty.
Cleavinger made a career-high 68 appearances in 2024 with Tampa Bay and finished with a 3.75 ERA. He has made one appearance so far in 2025, allowing two hits and one run across one inning.
He would join Thielbar in the Chicago bullpen and give manager Craig Counsell another option to come in and face left-handed hitters throughout the season. The return of Assad and Melendez to the Rays would give them both pitching depth and a young and upcoming infielder that they can bring up and develop through their system until he is ready to make his MLB debut.
