Alex Bregman’s free agency was quite a long, stretched-out rollercoaster ride. Not just fans, even he wasn’t sure where he would end up.

Thirty minutes. That’s how close he was to heading somewhere else before finally agreeing to become a Boston Red Sox.

“Thirty minutes before I ended up becoming a Red Sox, I was going somewhere else,” Bregman admitted just recently.

But where was it if not Boston? If you read between the lines and the contract offers he got it’s kind of clear– he might have thought he was headed to Detroit.

Throughout the off-season, the Detroit Tigers were all in on Alex Bregman. They made him their priority and they apparently put a six-year $171 million contract on the table.

Now that’s way more than the Boston Red Sox‘s $120 million deal given by for three years. And well, Bregman reportedly considered heading to the Detroit Tigers; even his agent, Scott Boras, confirmed so!

“Alex has great respect for the Detroit organization, its great players, and its heralded manager,” Boras mentioned to the Detroit Free Press. He also revealed how Bregman was interested in the Tiger’s vision. After their 2024 playoff run, Bregman seems to have seen that potential. And Boras mentioned, Bregman even asked him to initiate contract discussions.

In fact, Alex Bregman’s camp apparently sent the Tigers two counter-offers, both eliminating the deferred money. It seemed he was going to be in Detroit, but not at last!

Did Alex Bregman choose Boston or was it Boras’ masterstroke?

There was a deep mutual interest between the Detroit Tigers and Bregman parties. But there were some major roadblocks too.

Detroit refused to go beyond the $200 million, and second, they would not offer an opt-out after 2025. And that seems to have been the deal breaker.

The Boston Red Sox were forthcoming, and they offered Bregman opt-outs – after this season and the next. So, Breggy can very well use this as a prove-it year and hit his free agency and get a better deal.

It’s what many players do; look at Cody Bellinger– a fine example, who is now with the New York Yankees.

But the elephant in the room is whether Scott Boras steered the ship for Bregman to go to Boston.

Bregman revealed something that felt like he was in the dark. “It was my first time in free agency. You don’t know what to expect. After going through it, you don’t know until the last second, until everything is complete… It was an interesting experience, like you said. You kind of focus on what you can control in your training and listen to your agent.”

That last line—“listen to your agent”—is kind of telling.

And everyone knows how Boras is known to get big-ticket contracts. Look at Juan Soto!

So it won’t be surprising if he saw Boston as a one-year deal for Bregman. That way, he can enter free agency again and get a better deal elsewhere. Didn’t he do the same with Blake Snell this season?

But whether it was Bregman calling the shots or Boras leading – A-Breg is looking forward to his time with the Red Sox. “I’m a winning player. This is a winning organization. Those players are winning players. We have winning coaches here. I plan on winning here,” said Bregman, proving he is all in.

It remains to see what he does in Boston. Even though the season has not started, tension in the clubhouse has already started. Rafael Devers has made a huge deal of not his moving position to make way for Bregman. But the Red Sox didn’t bring a Gold Glove third baseman to sit on the sidelines, right?