When you reach free agency -- especially when you opt into the market by triggering a contract provision -- it's typically a good idea to keep the Yankees on either the back or front burner. The Yankees are the "presumed favorites" for every free agent at the start of the winter for a reason: because agents want them to be.
Unfortunately for Marcus Stroman, he's entering the market in the undesirable position of having already eliminated the Yankees (and, probably, Steve Cohen's Mets).
Stroman's career hit a fulcrum in Summer 2019 when he was traded to New York (of the blue and orange variety), leading to a two-way chain reaction where both Stroman and Brian Cashman fought to distance themselves from one another as thoroughly as possible. Reports leaked that Stroman threw a tantrum in the clubhouse when the Mets came calling instead of the Yankees. Stroman denied these reports (duh?), though his father told the media, "He was hoping it was the Yankees… He was kind of psyched, maybe hoping to go there. I’m not going to tell you that he wasn’t."
As FOX Sports noted at the time, Stroman's Yankees breadcrumbs ran deep until the bag was emptied by Cashman and company:
"Stroman liked a tweet on July 9th talking about the Yankees making a trade for him, and two weeks later tweeted he had been a second-half ‘savage’, clearly referencing Yankees manager Aaron Boone famously screaming to the home plate umpire that his players were 'SAVAGES IN THE BOX' (Stroman would later delete the tweet)."- FOX Sports
When pressed on why the under-.500 Mets felt like "going for it" with Stroman while the "Next Man Up" Yankees stood pat, Cashman claimed Stroman wouldn't be a "difference-maker" in his rotation -- in other words, the precursor to the Jordan Montgomery gaffe.
Every time Stroman has struggled over the past four years, Yankee fans have returned to his tweets scorning the team's rotation with glee. But the bottom line is, while the Stro Show has had his low moments, his overall body of work would have been welcomed in the Bronx, and still could be again if both parties hadn't torched the bridges between them.
Yankees target Marcus Stroman talked himself out of free agency consideration in 2019
Stroman opted out of the 2020 season, but his ERA has never eclipsed 4.00 in a campaign since the Yankees/Mets pivot point. His 3.77 ERA in Flushing down the stretch in '19 certainly would've "made a difference," especially considering Domingo Germán removed himself from the playoff rotation with his heinous actions down the stretch.
There was a time when he had become firmly acclimated to Team Mets, calling out "false media reports" about his locker room blowup again prior to the 2021 season. But even that branch withered over time; when Stroman left for Chicago, he torched Mets GM Billy Eppler and repeated his pattern of taking shots at an organization he didn't belong to.
The only difference here is he'd seen what we didn't behind closed doors with the Mets, and only had his own ideas of what lay beyond in the Bronx.
Stroman opted out of his $20+ million deal with the Cubs last week -- and somewhat surprisingly, after he faltered slightly down the stretch and battled injuries. He remains a very similar pitcher to the one he was in 2019, an excellent mid-rotation stabilizer who could fit nicely in a high variance Yankees rotation. The defensive infield behind him in the Bronx would cater to his skills, too, with Gold Glover Anthony Volpe officially ranking as a newly-minted Difference-Maker.
Instead, the Yankees will chase high-ceiling arms from overseas while trying to find a lefty bat for the fourth consecutive offseason. It's much more likely Stroman tweets about the team's lineup imbalance rather than joins them.