The Chicago Cubs have been active this offseason, trying to add talent to their 83-win team from 2024. So far, they have added a few pitchers, some depth pieces for the lineup, and the big ticket item, Kyle Tucker. Last weekend, the Cubs acquired another Houston Astro, Ryan Pressly. Pressly is the latest arm the front office has added to Craig Counsell’s bullpen, but he is likely not the last relief pitching target for the Chicago Cubs this offseason.
As the team makes room for Pressly in the bullpen, the Chicago Cubs are moving their full attention towards the free agent market for guys to fill out the back end of their bullpen. In seasons past, the bullpen has been unpredictable and unreliable, with a group of fringe major leaguers, struggling starters, and young, unproven arms. President of Baseball Operations Jed Hoyer is trying to address that this offseason with some quality veterans, and they are reportedly honing in on David Robertson, Carlos Estevez, and Kenley Jansen.
Chicago Cubs Eyeing Veteran Right-Handers
The Chicago Cubs are remaining active deep into hot stove season looking to add players to their bullpen. They just completed their second major trade with the Houston Astros. Earlier this offseason, they made a deal to acquire Kyle Tucker, and now they have added Ryan Pressly. That hasn’t stopped Jed Hoyer from evaluating the relief pitcher free-agent pool that is still out there waiting to be signed. Before the Los Angeles Dodgers signed Tanner Scott to a four-year, $72M deal, the Cubs had offered the left-hander a four-year, $66M contract.
With Scott and many others off the market as the offseason treks towards its final month, the Chicago Cubs have honed their immediate attention in on three names. They are determined to add some veterans to their bullpen, and if they aren’t able to land their top three targets now, they will look lower on their priority list for options before spring training. Brooks Raley, Phil Maton, and Ryne Stanek could be targeted on the horizon for Chicago, but as of now, they have their eyes set on David Robertson, Kenley Jansen, and Carlos Estevez.
Former Closers Recruited to Wrigley Field
David Robertson played with the Chicago Cubs earlier in his career, pitching as the club’s closer in 2022 before being traded at the deadline to the Philadelphia Phillies. Robertson showed that even as a veteran, he is capable of sustained production in high-leverage situations. Last season with Texas at age 39, Robertson set career-highs in innings with 72 and holds with 34. He pitched to the tune of a 3.00 ERA, 1.11 WHIP, and struck out 99 in 68 appearances. Despite turning 40 early in the season, the Cubs could use a familiar face like Robertson to support Ryan Pressly and the young arms in the bullpen.
Kenley Jansen has a less rosy relationship with the Chicago Cubs. As the long-time closer for the Los Angeles Dodgers, Jansen battled the Cubs throughout their postseason runs and often sent them back to the clubhouse after shutting the door in the ninth. That trend hasn’t changed for Jansen since. Even at 37, Jansen has been remarkably effective as a closer. Since leaving Los Angeles, he has been the closer for the Braves and Red Sox, closing 97 games in 163.1 innings with a 3.42 ERA over the last three seasons. If the market for Jansen as a closer isn’t as robust as he is hoping for, the Cubs are live to sign him as a set-up man.
Carlos Estevez is the youngest and likely the most affordable option of these three relievers for the Chicago Cubs to sign. Estevez, 32, pitched for the Los Angeles Angels and Philadelphia Phillies in 2024, posting the best season between himself, Robertson, and Jansen. Estevez had a 2.45 ERA, 0.91 WHIP, and 50 strikeouts in 55 innings across both teams. He has had experience as a closer in Colorado and Los Angeles but is more often used as a late-inning set-up man. If the Chicago Cubs want to add a pitcher with a longer runway to the back of their bullpen, Estevez could be the answer. His relative youth and familiarity as a set-up man could make the difference.
Final Thoughts
Chicago Cubs President of Baseball Operations Jed Hoyer did a great job of finishing up negotiations with the Houston Astros on a Ryan Pressly trade. Pressly needed to be the top priority for the Cubs front office, and once that got squared away, looking to add another proven arm in the free agent market is a great move. Robertson, Jansen, and Estevez could be impactful set-up men behind Pressly in Chicago, and having experienced, battle-tested arms in the bullpen for a team with playoff aspirations is critical and could add to what has already been a very active offseason for the Chicago Cubs.
If I had to pick just one of these three pitchers to add to the Chicago Cubs bullpen, it would be David Robertson. Not only does he have experience with the team and the city of Chicago, but he has been remarkably durable and consistent since leaving the Friendly Confines. The age concerns are prevalent yet diluted with the style in which he pitches. Robertson’s role as a middle reliever could be a hand-in-glove fit in front of Pressly. Adding Robertson, Jansen, or Estevez to the mix along with Pressly in one offseason and the Cubs front office might have turned their bullpen into one of the top units in the National League.
