Alex Bregman rumors: Cubs front office split, Red Sox indecision, Astros getting impatient?

The Alex Bregman sweepstakes are seemingly down to five teams: the Houston Astros, Detroit Tigers, Boston Red Sox, Toronto Blue Jays, and Chicago Cubs.

Each team left in the sweepstakes has their own selling point. The Red Sox and the Tigers both have coaches with direct connections to Bregman. The Blue Jays and Cubs would be World Series contenders with him. And the Astros are the incumbents in this race, with reportedly a deal worth over $150 million on the table.

As this stalemate drags on, let's dive into the rumors.

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Alex Bregman rumors: Cubs front office reportedly divided

The Cubs are seemingly the dark horse team in the race for Bregman. While they've seemed like a solid fit for a while, it was only after they brought in former Astros reliever Ryan Pressly that it truly seemed like the two sides could be the perfect fit. Chicago is seemingly going all-in to win in 2025 and their roster reflects that, and adding Bregman on a short-term deal would help push this team in the way they want to go.

But according to 670 The Score host Matt Spiegel, the Cubs front office is split on whether they want to pull the trigger or not.

On one hand, it's Bregman. Obviously any team that has the ability to add a star like him should. He's a superstar-level player that provides good defense and a great bat. The righty is a known winner with a track record to back that up. Chicago is looking to win now and Bregman is the ultimate win-now addition.

But on the other hand, the Cubs are looking to add top prospect Matt Shaw to the starting lineup to begin the season. Shaw is likely to step in and play third base. If they add Bregman, it could stunt Shaw's growth. Chicago would likely trade Nico Hoerner in this scenario, but if Bregman opts out after a few years, they would be in a tough spot.

Alex Bregman rumors: Red Sox at a tough crossroads for Bregman

Realistically, the Red Sox should be the favorites in the Bregman sweepstakes. Boston had enough money to spend to offer Juan Soto a deal reportedly worth $700 million. Now, the Red Sox haven't spent any more than $100 million this winter, which leaves the door swung wide open for them to win the bidding war for Bregman — even if they have to meet Scott Boras' asking price of $200 million.

Peter Abraham of the Boston Globe recently detailed the division in the Boston front office that could be leading to a crossroads for Bregman.

"Agents have come away believing Alex Cora and Sam Kennedy want to add a middle-of-the-order hitter. But Breslow, John Henry, and Tom Werner have been cautious. It explains why the Red Sox have so far done nothing to improve their lineup this offseason, even after losing outfielder Tyler O’Neill to the Orioles as a free agent. It also explains, in part, why Breslow has yet to sign a free-agent hitter to a major league contract during his 15 months as chief baseball officer."

It seems like the Boston front office, at least Breslow and Henry, are much more willing to bank on their top prospects rather than chase a $200 million veteran to fill out the lineup. This could be quite a risk for Boston, but if Breslow and Henry are right, they would be saving quite a bit of money by letting Bregman sign elsewhere.

Alex Bregman rumors: Astros fans growing impatient as Bregman negotiations stall

There might not be a fan base in baseball that has been through more of a roller coaster ride with the Bregman sweepstakes than the Astros have. Houston began the offseason with full belief that Bregman would be returning on a massive deal. He's a franchise superstar and a legend of the team. The front office made him the top priority and reportedly offered well over $150 million.

But Bregman declined and continued to test free agency. Houston opted to sign Christian Walker and trade for Isaac Paredes to replace their former star third baseman. After negotiating with a few other teams and those stalling out, the Astros reversed back to Bregman. Now it seems like the negotiations are going nowhere once again. This time, though, blame seems to be shifting toward the player.

It seems like the fans just want this saga to end. When Bregman signs and gives his reasons for signing where he does, the fans are going to see right through the lies. Everybody understands that this is just about the money.