How did Red Sox miss on Marcus Stroman's favorable price, Craig Breslow connection?

After having a contentious relationship with the franchise for four years, the New York Yankees signed Marcus Stroman on Thursday night in what was a shocker.

The friction between the two sides began in 2019 when New York's general manager Brian Cashman said he didn't think Stroman would be "a difference maker" on his playoff squad. Stroman took that personally.

The right-hander took to Twitter at the time to share his distaste for the Yankees organization — his childhood favorite team. He and Yankee fans have butted heads ever since.

Despite the two sides not getting along, New York got a deal done with Stroman before the Red Sox could. Boston had reportedly been eyeing Stroman to add depth to its current, lackluster starting rotation.

There's even a connection to Stroman in the Sox's front office. New Chief Baseball Officer Craig Breslow arrived in Boston from the North Side of Chicago this offseason. He and Stroman spent two years together with the Cubs.

After seeing the price the Yankees got for the 32-year-old hurler, the Red Sox should wish they acted quicker to secure his signature. Stroman signed for two years and $37 million, per Joel Sherman of New York Post. That's just $18 million per year — a bargain for a pitcher of Stroman's caliber.

Red Sox missed out on signing Marcus Stroman for a great price

Boston has been losing out all winter long. After claiming to be in on Shohei Ohtani, Yoshinobu Yamamoto, Shōta Imanaga, Teoscar Hernández, and now Stroman, the Sox have been consistently beaten in bidding wars, mostly due to uncompetitive offers from the front office. Some of them have been laughable, like the two-year, $28 million offer they presented to Hernández. With a previous connection in the front office, it's hard to believe Boston couldn't work out a deal with Stroman if he was willing to sign with a team he previously, openly despised for such a low price.

It's possible Stroman lowered his asking price when he sat down with the front office in the Bronx. He and his agent had expressed interest in signing with the Yankees in recent weeks, and New York reportedly declined to make an offer at the time. They changed their tune quickly after meeting with him. Maybe the Red Sox could have spun a similar offer or a slightly bigger one.

But now that Boston is down yet another pitching target, the front office needs to pivot again. Rumors have surfaced that the Sox are still in on 2023 World Series champion Jordan Montgomery, who would come at a much higher price. Boston hasn't delivered on any pitchers it has claimed to be "in on" this offseason, so the words have little meaning to fans now.

The deal is even worse for the Sox when you think about the batting order having to contend with a freshly motivated Stroman multiple times this year — he has a target on his back in the eyes of Yankee fans, and he's surely eager to prove them wrong. Sox fans just better hope he serves as more of a distraction for the Yankees given his potential to upend the team chemistry.

The Red Sox are running out of time and options to make the team better, and other clubs out there seem to have reached this conclusion faster than they have. If Boston has plans to improve in 2024, it needs to act soon. The clock is ticking.

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