Ryan Pressly is the most decorated playoff reliever in Houston Astros' history, a former closer with 14 career postseason saves (most in franchise history and fifth most all-time) and a 17-inning scoreless streak across the 2022 and 2023 postseasons.

The Chicago Cubs have traded for Kyle Tucker and Ryan Pressly from the Astros and are one of possible teams for Alex Bregman in free agency.

Ryan Pressly will suit up for the Chicago Cubs this year after spending seven seasons with the Houston Astros. Per The Athletic's Chandler Rome,

Pressly never aired any grievances publicly and continued to serve as a model teammate throughout his uneven 2024 season.

The Chicago Cubs have acquired right-hander Ryan Pressly and cash from the Houston Astros for minor league pitcher Juan Bello.

Pressly has already spoken with Cubs manager Craig Counsell and Cubs president of baseball operations Jed Hoyer.

The Houston Astros recently made a blockbuster trade to ship Ryan Pressly to the Chicago Cubs, which could be the key to an Alex Bregman reunion.

The Chicago Cubs could turn to free agency to boost their bullpen after swinging a blockbuster trade for Ryan Pressly.

The Houston Astros just shook up MLB with a blockbuster trade, sending veteran closer Ryan Pressly to the Chicago Cubs in exchange for minor league pitcher Juan Bello and cash considerations. This move isn't just about bolstering the Cubs' bullpen—it could be the key to the Astros’ potential reunion with Alex Bregman.

So far this winter, the Cubs have added two key members of the Astros, Kyle Tucker and Ryan Pressly, both via trade with Houston.

The Astros-Ryan Pressly divorce may have been in the works since last winter. Houston general manager Dana Brown admitted Tuesday that his relationship with the closer “took a slightly different turn” when the franchise signed Josh Hader to a five-year, $95 million contract a year ago, pushing Pressly into a setup man role.