Alex Bregman is officially a Chicago Cub, and with that, any lingering hope of him donning the Old English “D” has been put to rest-again. But let’s be honest: that ship sailed a long time ago. The Tigers weren’t involved in Bregman’s free agency this offseason, and while that might feel like old news, it’s still worth unpacking what it means in the broader context of Detroit’s current direction.
First, let’s rewind to last offseason, when there was some smoke around Bregman and Detroit. At the time, there were reports that talks between Bregman’s camp-led by agent Scott Boras-and Tigers president of baseball operations Scott Harris didn’t go particularly well.
Whether it was a mismatch in expectations, a philosophical disconnect, or just business as usual, things fizzled fast. And that left a sour taste in the mouths of fans who briefly entertained the idea of Bregman anchoring the infield at Comerica Park.
Fast forward to this winter, and Bregman’s name kept surfacing-just not in connection with Detroit. His free agency saga became one of the most closely watched in baseball, especially as his negotiations with the Red Sox grew increasingly complicated.
The sticking point? A no-trade clause.
When Boston wouldn’t budge, Bregman walked, eventually landing a five-year, $175 million deal with the Cubs.
That number is significant. Had Bregman signed with the Tigers last offseason for the reported six years and $171.5 million, he’d have left money on the table.
Instead, he took a one-year stop in Boston, earned roughly $35 million, and then cashed in again with Chicago. It’s a classic Boras move-bet on the market, play the long game, and maximize the payday.
And it worked.
From Detroit’s perspective, though, there was never a serious re-engagement this winter. Despite the national buzz and the late twists in Bregman’s free agency, the Tigers stayed on the sidelines.
That decision aligns with what Harris has consistently said: Detroit wants players who want to be in Detroit. Bregman clearly had other priorities, and that’s fine.
He earned the right to explore the market and find the best fit-and paycheck-for himself.
Still, it’s hard not to wonder what could’ve been. Had Bregman signed with the Tigers last year, would he have become the long-term leader of this young, promising roster?
Would Detroit have pushed deeper into the postseason? Would he have found the kind of organizational fit he was looking for?
We’ll never know, and at this point, it doesn’t really matter. The Tigers are building something with players who are fully bought in.
That’s the foundation Harris is laying, and it’s starting to show signs of real progress. Bregman, meanwhile, gets a fresh start in Chicago, a team that’s clearly all-in on competing now.
So, while Bregman’s name might still stir emotions in Detroit-frustration, curiosity, maybe even a little relief-it’s probably time to move on. The Tigers did. And unless the Cubs are rolling into town, there’s really no reason to revisit what was never going to be.