Kyle Tucker of the Houston Astros (left) congratulates pitcher Ryan Pressly after the Astros defeated the White Sox 6-1 to win Game 1 of the American League Division Series on Oct. 7, 2021, in Houston, Texas. Both are now Cubs.

Alex Bregman remains a free agent, with the Astros and Cubs among potential remaining suitors for the third baseman. Chicago already has acquired two players from Houston's championship era in Ryan Pressly and Kyle Tucker via separate trades.

Houston Astros relief pitcher Ryan Pressly walks back onto the mound after throwing a wild pitch that allowed Detroit Tigers’ Kerry Carpenter to score in the eighth inning of Game 2 of an AL Wild Card Series baseball game, Oct. 2, 2024, in Houston.

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

The Chicago Cubs could look to sign veteran righty David Robertson after their blockbuster trade for Ryan Pressly.

The Ryan Pressly trade moves the Astros under the threshold for the competitive balance tax and possibly in position for another deal.

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

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

Ryan Pressly had to make a choice. As he mulled over with his wife, family and friends whether to waive his no-trade clause to accept a move from the Houston Astros to the Chicago Cubs, the veteran reliever considered the opportunity to close games again — though it would come at the cost of leaving Houston,

New Chicago Cubs pitcher Ryan Pressly was interviewed by Marquee Sports Network's Cole Wright and Bruce Levine to discuss what drew him to Chicago, the opportun

The Houston Astros completed the trade of relief pitcher Ryan Pressly and cash considerations to the Chicago Cubs Tuesday, in exchange for minor league pitching prospect Juan Bello.