Ryan Pressly Hints at Possible Reunion with Alex Bregman on the Cubs

Chicago Cubs fans are buzzing about the possibility of Alex Bregman joining the team, and recent comments from Ryan Pressly have only added fuel to the speculation. The veteran pitcher, who was recently traded from the Houston Astros, has openly expressed his desire to play alongside Bregman again.

Could Bregman Join the Cubs?

During a media session at the Cubs’ spring training facility, Jameson Taillon was asked if Pressly and Kyle Tucker, both former teammates of Bregman in Houston, were actively recruiting him to Chicago. Taillon remained diplomatic but acknowledged that Bregman is highly regarded among players.

“I don’t know about recruiting,” Taillon said with a smile. “But I know those guys speak very highly of him. And I have definitely heard them communicate that out loud.”

Pressly, who is expected to serve as the Cubs’ primary closer this season, was more direct in his remarks.

“I don’t think it’s recruiting,” Pressly said. “It’s just more of like, ‘Hey, how are you doing? What’re you hearing?’ Stuff like that. Would I like to play with him? 1,000% – I would love to play with him. But he’s got to make the best decision for his family.”

The Financial Hurdles in Signing Bregman

While the Cubs remain strongly linked to Bregman in various reports, the financial implications of signing him present a challenge. Bregman declined a qualifying offer for 2025, which means any team signing him would incur penalties.

For the Cubs, this would mean forfeiting their second- and fifth-highest picks in the 2025 MLB Draft, along with losing $1 million in international bonus pool money. Additionally, the team is aiming to stay under the Competitive Balance Tax (CBT) threshold, which sits at $241 million this season. Reports indicate the Cubs currently have around $30 million in CBT payroll flexibility, meaning adding Bregman could require some creative financial maneuvering.

Cubs’ Plan for Third Base Without Bregman

If the Cubs are unable to land Bregman, top prospect Matt Shaw could be the frontrunner for the starting third base role. Ranked No. 19 on MLB Pipeline’s Top 100 Prospects, Shaw has impressed in the minors, and Cubs President Jed Hoyer emphasized that the team is giving him a chance to earn the job in spring training.

“We’re not anointing anybody,” Hoyer said. “We’ll see how things play out, but we’re always keeping an eye on opportunities.”

Are the Cubs Done Making Moves?

While Bregman remains a top target, the Cubs are also rumored to be considering Justin Turner as a backup first baseman and could still look to add pitching depth. Cubs Manager Craig Counsell made it clear that the front office is actively exploring options.

“We’re not done,” Counsell said. “I don’t think you ever consider yourself done building a roster. We’re always looking at options.”

As spring training unfolds, Cubs fans will be watching closely to see if Bregman joins his former teammates in Chicago.