Chicago Cubs Possibly Trading for 2-Time All-Star Reliever

The Chicago Cubs are rumored to be in serious talks with the Houston Astros about a trade for two-time All-Star reliever Ryan Pressly. Pressly, 36, has a full no-trade clause and has squashed potential deals that would send him to the East or West Coasts. However, he has reportedly not been averse to a trade to the Cubs, and as speculation that he would waive the clause for them ramps up, it’s looking more and more likely that a move will be made.

Pressly is in the final year of his contract, enticing Houston to get something in return for him and make a deal to send their former closer to Chicago. The Cubs have been in dire need of a closer, and adding Pressly would go a long way toward fixing their bullpen, a unit that was cobbled together through much of the last three seasons. Getting back to his role as a closer while still pitching for a team with playoff aspirations may be enough for Pressly to accept a trade to the Cubs.

Chicago Cubs in Talks with Houston for Ryan Pressly

Speculation intensified yesterday that one of the most decorated relievers in MLB over the last decade could be on the move and in a hurry. Reports emanating around Chicago and Houston say that the two sides are in deep talks to make a trade surrounding Pressly. Bob Nightengale and Jon Heyman were among the first to report the talks, and if their reporting is accurate, a deal may be in the pipeline sooner rather than later.

There are some constraints on any deal that could get made. Pressly, 36, has a full no-trade clause and has indicated in the past that he is not willing to waive it. This offseason, he has shut down any trade offers that would have sent him elsewhere. Noticeably, though, he hasn’t shut down any deal to the Midwest and the Friendly Confines of Wrigley Field. With the Cubs looking for a proven closer at the back end of their bullpen and the Astros looking to shed payroll and free up money to retain Alex Bregman, an agreement between the clubs is looking favorable for both sides.

A package for Pressly would likely involve Houston paying some of his 2025 salary to enhance the return they bring back from Chicago. He is due $14M in 2025, and with Josh Hader entrenched as their closer, Houston could be selling their top set-up man ahead of his impending 2025 free agency. With one of the worst farm systems in MLB, eating some money in 2025 to add better prospects to their minor league system could be the move for the Astros, especially when dealing with the Cubs, who have one of the best farm systems in baseball.

Adding a Proven Arm to the Bullpen

All of the conversations surrounding Pressly have accelerated in the last couple of hours, and some of baseball’s top insiders are tracking the progression of a deal. Jon Heyman posted, “Astros relief star Ryan Pressly, pursued seriously by three teams, has full no-trade and told the Astros he’s disinclined to go East or West. So that’s a “no” for Jays, one of the interested teams. He hasn’t committed either way yet on Cubs.” Bob Nightengale is more ardent in his analysis of the possibility of a trade, posting, “The Chicago Cubs on verge of acquiring closer Ryan Pressly from the Astros.”

If Pressly were to join the Chicago Cubs, he would become their top reliever instantly. Last season was one of change and upheaval for him, his first as a set-up man in Houston. His manager, Joe Espada, commented on the role change for Pressly, saying, “I’m used to Pressly coming in in the ninth and [shutting] the door, so it took some time for him to adjust. Once he did, I think he got it going, and I think he threw some big innings for us.”

In 2024, Pressly had a 3.49 ERA, 1.34 WHIP, and 58 K in 56.2 IP. For his 12-year career in Minnesota and Houston, he has a 3.27 ERA, 1.16 WHIP, and 112 saves. If he became available for the Cubs, he would supplant Porter Hodge as the closer, bumping everybody down a peg in the bullpen for Craig Counsell. His best baseball may be behind him, but if he can be added to the Chicago bullpen, they become a much scarier team to battle in the NL Central.

Final Thoughts

Adding Ryan Pressly to the Cubs bullpen would do wonders for Craig Counsell’s ball club. The proven veteran has competed at the highest level in the sport for years, and bringing his treasure trove of wisdom and know-how to a team with one of the younger bullpens in MLB could have enormous benefits. It’s unclear where he stands as an aging reliever with his ability to produce. If last season is a sign of things to come, the Cubs must ensure they don’t give up a haul for the 36-year-old.

Even with forecasting his 2025 to be more like 2024, Pressly would be the best and most reliable arm in the Chicago Cubs bullpen. Taking on his $14M salary may be startling for some other teams, but for Jed Hoyer and his front office regime, who are in a lame-duck season and desperate to get off the 83-win hamster wheel they’ve been on for the last two seasons, it’s a deal they are willing to make. And if reports about Pressly’s willingness to waive his no-trade clause for a Midwest contender are true, the Cubs appear to be the frontrunner to land the World Series champion.