The Chicago Cubs, apparently, weren’t as close to signing free agent third baseman Alex Bregman as reported.
The push for Bregman was a crazy one. Chicago showed no interest in Bregman for almost the entirety of the offseason and then, as spring training approached, they were suddenly in hot pursuit of the veteran star and former Houston Astro. Or not.
In a recent appearance on the Foul Territory show, Bregman talked about the closing moments of his free agency and indirectly revealed that the Cubs were not among the finalists for his services after all.
“It was kind of crazy…I met with a lot of teams and, honestly, everything just happened in, like, the last 30 minutes,” Bregman said. “We thought we were going somewhere else the entire time and then, in like the last 30 minutes, we talked to Boston…and the deal got done…”
When pressed to name the team that came in second place to the Red Sox, the Cubs were NOT them.
The Chicago Cubs Were Not Serious Suitors for Alex Bregman

“We thought we were going to be in Detroit the entire time, honestly, and then at the last second, Boston kind of came in,” Bregman revealed.
And that certainly flies in the face of what many believe, especially in Chicago.
The Red Sox, using some deferred money, would end up signing the 30-year-old Bregman to a 3-year, $120 million contract with an opt out after 2025 and 2026. The Tigers’ offer was six years for $171.5 million with an opt out after 2026. The Cubs, meanwhile, reportedly offered Bregman a 4-year, $115 million deal with opt outs after the 2026 and 2027 season.
As things turned out, the Cubs’ proposal wasn’t even necessarily in the top three, as the Astros’ offer of six years at $156 million could be seen as a better deal.
A Failed Offseason?

So, if the Cubs were not really considered serious suitors for Bregman, that kind of casts a bit of a cloud over this offseason and puts into question whether ownership was really as “all in” as they claimed to be headed into 2025.
They whiffed, big time, on Bregman. They also lost out on closer Tanner Scott. They never even got into the race to sign one of the top front-of-rotation starters available via free agency. Heck, they even made new star pickup Kyle Tucker go to arbitration for an extra $2 million
All of this puts a target on chairman Tom Ricketts and the Ricketts family ownership as the question is once again posed– why isn’t this major market team spending like a major market team?
Buster Olney of ESPN, in a now-infamous takedown of the Ricketts’ frugal ways, blasted Cubs ownership shortly after Bregman signed with Boston:
“Hurricane Milton wrecked the Tampa Bay Rays’ ballpark last fall, leaving them without a stadium. For this season, they will play their home games in the Yankees’ spring training facility, which has a capacity in the range of 11,000 fans.
And yet the Rays have outspent the Chicago Cubs in free agency this winter.
Which says so much more about the conduct of the big-market Cubs than about the Rays. Last week, the Cubs were outbid by multiple teams for the services of All-Star third baseman Alex Bregman, and the question that should hang over the franchise is: why? Why aren’t the Cubs spending more?”
Mid-Market Spending From A Major Market Team

Olney’s rhetorical question has been answered several times since that rant. Ricketts, himself, has been doing interviews where he doubles down on his budget baseball philosophies and, before that, issued the hilariously tone deaf assertion that the Cubs are merely breaking even each year.
In a recent CNBC interview, he even looks back on the time when he maybe, possibly considered signing a free agent Bryce Harper, but ultimately didn’t.
“We spent a lot of time thinking about what Bryce Harper’s worth as a free agent, sitting with Theo [Epstein], talking about that,” Ricketts said. “That’s one that we kicked around that, obviously, we never executed on.”
And, unfortunately, that looks to be about as close as the Cubs will get to signing any really big, impactful deals– a thought and, maybe, a token offer. That’s it.
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