The Boston Red Sox have started to really click over the last month with a 48-40 record and the third American League Wild Card spot in hand.
Winning has historically healed all, making the Red Sox's disappointing offseason more of a distant memory than a constant reminder of what should have been.
However, Red Sox chief baseball officer Craig Breslow was expected to deliver a big offseason with backing from ownership and that did not happen. One of the bigger targets was left-hander Jordan Montgomery -- who was heavily linked to Boston all winter.
As it turns out, the southpaw did not want to play for the Red Sox, who are coming off two last-place finishes in the AL East simply because ownership was content with failure.
"Montgomery could have signed a multi-year deal with Boston earlier and gone to spring training, but he didn’t want to go there and was holding out for a (Texas) Rangers return," the New York Post's Jon Heyman reported Thursday.
Montgomery posted a 3.20 ERA with a 166-to-48 strikeout-to-walk ratio, .247 batting average against and 1.19 WHIP in 188 2/3 innings between his time with the St. Louis Cardinals and the Rangers in 2023.
What has ensued since, will make Breslow feel great about his inability to lock down the lefty. He's posted a 6.44 ERA with a 1.68 WHIP for the Arizona Diamondbacks after settling for a one-year, $25 million contract that includes a vesting option for 2025.
While this specific instance might have been a fruitful mistake, it's important to note that some marquee players do not want to play in Boston thanks to a distracted ownership group. The allure of playing in a big market while calling Fenway Park home should be a massive advantage in free agency. Principal owner John Henry has found a way to turn it into a flaw.
For Montgomery, he'd be wise to keep all his options open. He's no longer deemed to highly-coveted frontline starter he once was.
