The Chicago Cubs have finalized a deal that nets them Houston Astros relief pitcher Ryan Pressly. Pressly has been one of the lynchpins of Houston’s run of dominance in the American League and is one of the top postseason performers in all of baseball. The deal was finalized after Pressly agreed to waive his no-trade clause for the Chicago Cubs. In exchange for Pressly and cash, the Cubs are sending 20-year-old right-handed pitching prospect Juan Bello.
Ryan Pressly slides into the closer role with the Chicago Cubs after having huge success with the Houston Astros for seven seasons, including three as the full-time closer. The addition of a proven, late-inning reliever could pay huge dividends for a Cubs team that last year played in more than their share of one-run games and blew 27 saves. Having Pressly in a bullpen that is talented yet inexperienced can help other pitchers hone in on smaller roles and make the Chicago Cubs bullpen a strength for Craig Counsell. The trade for Pressly is likely not the last move the team will make before spring training begins next month.
Ryan Pressly Headed to Chicago Cubs
The Chicago Cubs broke into the NFL conference championship news cycle when it was announced that they had finalized a deal with the Houston Astros to acquire Ryan Pressly. Pressly had been denying the Astros potential trade destinations so far this offseason via his no-trade clause but accepted the trade that is sending him to Chicago. To go along with Pressly, the Astros are paying some of his $14M salary in 2025. In exchange for Pressly, the Chicago Cubs are sending 20-year-old right-handed pitcher Juan Bello to Houston. Bello has played with Chicago’s A-affiliate since being signed by the team.
This deal comes as the Houston Astros are trying to create payroll space to resign Alex Bregman, whose sweepstakes are still ongoing. Pressly had been demoted out of his closing role in Houston after they signed Josh Hader before the 2024 season. Pressly now heads to Wrigley Field, where he will return to the closing role and try to lift the Chicago Cubs from above .500 to a playoff team and pennant contender in the National League. He is one of the more decorated active postseason relievers, with a 2.78 ERA, 1.08 WHIP, and 60 strikeouts in 45.1 innings in his postseason career.
Trade Fallout
For the Houston Astros, this trade weakens their bullpen but gives them more financial freedom moving forward. The most likely use of those extra funds is adding resources to their negotiations with Alex Bregman, who is currently negotiating with three other teams in addition to the Astros. Houston’s pitching depth has been one of the hallmarks of their perennial contention in the American League, and they have other proven bullpen arms on the roster, making the trade of the 36-year-old Pressly and the acquisition of the 20-year-old Bello a sensible move for the team with the worst farm system in baseball.
For the Chicago Cubs, the addition of Pressly signifies an urgency that has been lacking in recent years. In their second trade with Houston this offseason after acquiring Kyle Tucker last month, they have signaled that they aren’t content with another season missing the playoffs, and in the final year of his contract, Chicago Cubs President of Baseball Operations Jed Hoyer is pulling out the stops. Adding Pressly to this bullpen creates more certainty and clarity for Craig Counsell when it comes to managing this group, which has been unpredictable and unreliable over the last two seasons.
Getting Pressly back into a closing role should help him get back into a rhythm that he struggled to maintain last season. In 2024, Pressly had a 3.49 ERA, 1.34 WHIP, and 58 K in 56.2 IP. For comparison, during his 12-year career in Minnesota and Houston, he has a 3.27 ERA and 1.16 WHIP. Pressly supplants Porter Hodge as the closer, bumping everybody down a peg in the bullpen. Even if his best baseball is behind him, added to this Chicago bullpen, Ryan Pressly helps them become a much stronger unit and makes the Cubs a scarier team to battle in the NL Central this season.
Final Thoughts
The Chicago Cubs desperately needed to make this move. After missing out on some of the other free agent relievers this offseason, most notably Tanner Scott, they needed to secure one of the better arms on the market and they did just that with the acquisition of Ryan Pressly. The shrinking market for his services due to his no-trade clause greased the skids for the Cubs and made trading for him much easier and clearer. After making a couple of big moves earlier this offseason, Jed Hoyer made his best trade Sunday afternoon. Juan Bello may end up being an asset, but getting Pressly is more valuable.
He may have had a year off from a closing role, but I’m confident that he will pick up close to where he left off in 2023. Even if he begins to diminish in his age-36 season, what he is capable of providing for this Chicago Cubs team is far better than what they have gotten in recent years from the back end of their bullpen. Even when the ninth inning was taken care of in the last few seasons, it was never consistent. Slotting the current bullpen arms down a peg to make room for Pressly not only helps them, but creates a bigger buffer and safety net for the starting rotation, something they lacked last season.
