It feels quite silly on many levels to argue that Jordan Montgomery should pack up and return to the Yankees this offseason. The Yankees were, of course, the team that diminished his talents and disrespected him on the way out the door last summer. Brian Cashman was the GM who claimed Montgomery wouldn't be making playoff starts in the Bronx anytime soon, ha ha, he he, only for him to find himself under Mike Maddux and dominate with the Cardinals and Rangers (occasionally on the road in Houston).
And, quite pertinently, the Yankees were the organization that uprooted him and his fiancée, who was unable to finish medical school as planned thanks to the discomforting reality of the business of baseball. The Yankees "summoned" Montgomery to Cashman's office 10 or 15 minutes before the deadline, per Ken Rosenthal, and broke the couple's shared heart in one fell swoop. The lefty's fiancée was set to start a residency program at New York's Mount Sinai hospital that would keep both parties under the same roof. She'd begun it the day before the trade deadline, and now was being abandoned for St. Louis. Those arguments ... don't get forgotten, and Cashman and Co. were entirely to blame.
All of these complicating factors seem to significantly lessen the likelihood that Monty throws caution to the wind and actively seeks out the organization that spurned him 15 months ago.
But when the Red Sox are chasing him from his own backyard, following his literal move to Boston, it feels 1,000 times sillier still to even bother considering it.
MLB Rumors: Yankees can't beat Jordan Montgomery's "hometown" discount in Boston
Yes, less than two years after building their whole lives around New York and Mount Sinai, the Montgomeries now live in Boston so that McKenzie Dirr-Montgomery can complete her dermatology program. The lefty is tossing at Boston College, where he awaits word on his next destination, though we can fill in the blanks for him if he really wants.
In 2022, Montgomery's wife dictated her medical journey so the two parties could stay in the same city. Now, over the past few weeks, she's figured out a way to land in Boston. Yeah, surely that has nothing to do with Montgomery's free agency plans. Just a total coincidence that their license plate now reads "BOS LHP". Absolutely no significance to their doormat reading "F*** CashGod". All just an ever-growing pile of astounding bits of serendipity.
The Red Sox have reportedly prioritized Montgomery this offseason, while Montgomery and his wife have actively prioritized the city of Boston. If you weren't sold on the Yankees adding $50 million to whatever projected Montgomery extension cost they had in mind back in July 2022 and putting their tail between their legs to bring him home, hopefully this stomps out the last bit of misguided hope you had about the process. He's going to face the Yankees four times a year and he's going to shove for three of them. At least his wife will be able to treat the resulting sick burns.