Chances are that Ryan Pressly will become a Cub soon. The Houston Astros are very eager to free up some payroll and bring back their star third baseman Alex Bregman. Trading Pressly would free up a significant chunk. Houston is already over the first luxury tax threshold, and acquiring Bregman would actually surpass the second threshold. 

And do not forget that Houston is not a first time offender so there’s that fine too! So much money for Alex Bregman? Sure he is a cornerstone for the franchise but still, every player has a value. The club had also traded Kyle Tucker last month, and now they are doing the same with Ryan Pressly. However, the 36-year-old has a no-trade-clause and whether he is willing to waive that for the Cubs is still not known. 

MLB insider weighs in on Ryan Pressly’s possible trade   

On a recent sit down with Foul Territory podcast, Ken Rosenthal shared his thoughts about the whole Ryan Pressly situation. Rosenthal said, “He was not happy when they brought Hader over him And you can understand where he’s coming from right? This guy had an amazing postseason record for them. Josh Hader is Josh Hader but I don’t need to tell you guys, his pride was wounded and now, yes, he can go back and be Prime Pressly back in the game for Cubs.” 

The Toronto Blue Jays and a mystery West Coast team are also reportedly in the mix for Ryan Pressly according to The Athletic.  The Texas native had found himself in a bit of a tricky spot last season after Houston brought in All-Star closer Josh Hader. That move led to Pressly being demoted in the bullpen hierarchy, but don’t let that cloud your judgment of him—Pressly’s still got a lot left in the tank. While it might’ve been a tough pill to swallow at the time, the 36-year-old’s pedigree, especially in high-leverage situations, will make him an important part of the Cubs.  

What will the Chicago Cubs gain? 

Ryan Pressly, at 36, is not just another veteran who’s been around a while—he’s a proven winner. With 17 postseason appearances and a solid 2.78 ERA in those high-stakes games, he helped guide the Astros to a World Series title in 2022. If the Cubs manage to snag him, he’d immediately become the most accomplished pitcher in their bullpen at Wrigley.

But let’s not sugarcoat everything—last season wasn’t Pressly’s best. His strikeout rate took a noticeable dip, dropping from 35.7% in 2022 to 23.8%. Plus, his fastball velocity dropped to 93.6 mph, a career-low after sitting comfortably in the 95-96 mph range for most of his career. That’s a noticeable change, especially when you’re talking about a guy whose bread and butter was his ability to blow it past hitters.

Here’s the thing, though: while that drop in velocity might raise an eyebrow, it’s not necessarily a cause for panic. The Cubs know what they’re getting in Pressly. The guy has elite pitchability. He’s not just a guy who relies on pure stuff—he’s a master of spinning the ball, and the 36-year-old has been finding ways to succeed with it for years. Instead of forcing the fastball, we could see Ryan Pressly shift more toward his slider and curveball, two pitches that have long been deadly in his arsenal.