“This has been the most difficult decision we have made as a family. It has been an incredible ride,” Pressly posted on X, formerly Twitter. “THANK YOU HOUSTON. You have been, and always will be, home. You believed in us and helped us make our dreams come true. From the first pitch to the final out, every moment here has been unforgettable. We are forever grateful for the fans, teammates, friends that have become family, and the countless memories. Thank you for everything. Houston, you have our hearts.”

Pressly started his career with the Minnesota Twins and was dealt to the Astros during the 2018 season. He spent seven years in Houston, making two All-Star Game appearances and getting the last out of the 2022 World Series. But Josh Hader’s historic contract pushed Pressly out of the closer role. He should be back in the ninth inning in Chicago.

The Astros continue to re-tool amid historic streak

The Astros fell short of the American League Championship Series for the first time since 2016 in 2024. As the Chiefs have in the NFL, Houston has dominated their side of the bracket for nearly a decade. But the team needs improvements to compete with a rising middle-class of American League teams.

Pressly is far from the only player the Astros have lost this offseason. Tucker is also on the Cubs and Alex Bregman is still available in free agency. The connection to the first championship is still there in Jose Altuve and Yordan Alvarez is still a dominant power hitter. But the Astros have unquestionably taken a step back from their high between 2017-2022.

The offseason is, of course, not over. Bregman could return to Houston despite multiple attempts from the team to sign him. Bringing his bat back to the lineup would help them compete in the American League West. But if he decides to go elsewhere, they could be leaning on Isaac Paredes more than originally planned.

Ryan Pressly will close games for the Cubs after a great run with the Astros. Will it help Chicago win the NL Central and end their playoff drought?