Craig Breslow Makes Honest Admission About Garrett Crochet Negotiations

Deadlines spur action — just ask Garrett Crochet and the Boston Red Sox.

Crochet is $170 million richer in part because he set a deadline for negotiations with his new team, but given the talent and potential he presents, the Red Sox were hellbent on finding a way to get something done. So, while Crochet insisted he wouldn’t negotiate beyond Opening Day, he officially signed a six-year contract extension Tuesday — nearly a week after the 2025 season started.

That Crochet and the Red Sox could find common ground on a deal even after Crochet’s self-imposed deadline is a testament to all involved. It certainly looks like the sort of agreement that will benefit both sides, but there were times where doubt crept into the head of chief baseball officer Craig Breslow as he and Crochet’s camp negotiated.

“These conversations have gone on for months now,” Breslow revealed on the latest episode of NESN’s “310 To Left” podcast, adding, “there were times we felt like we were really close and times we felt like we were miles apart.”

The good news for both sides is that they were able to get close enough to continue negotiations even after Crochet threw his first regular-season pitch in a Boston uniform after an offseason blockbuster trade with the White Sox.

“The conversations were always respectful and productive,” Breslow said, revealing Crochet was impressed by the organization, by Boston and the long-term future of the Red Sox.

The deadline loomed, though.

“Approaching Opening Day, I was not confident that there was a deal to be had, at least in this go-round of conversations,” Breslow said.

” … both sides were prepared to table the conversations save for one more return to the negotiating (table). It starts to draw out a more realistic look at positions and gives each side a chance to peek behind the curtain and say ‘Where can we get this done?'”

Ultimately, that allowed both sides to see they’d benefit from each other, and a massive deal was reached. That agreement will make Crochet a very rich man while also giving the Red Sox a legitimate No. 1 starter atop their rotation for the foreseeable future.