Red Sox accidentally picked Yankees fan to sponsor jerseys for next decade


Like it or not, jersey sponsorships are coming to MLB, and America’s highest-profile teams are beginning to get their ducks in a row to find a local brand that perfectly exemplifies their regional attitude.

The Red Sox went first. Swing and a miss.

Someday soon, the New York Yankees will announce that their iconic pinstripes, already smudged a few years back by the Nike logo, will be acquiring a KITH patch or a Papaya King square and we’re all going to have to be alright with the baseball world laughing at us.

And, on that day, at least we’ll be able to remind ourselves of the time the Red Sox signed over their jersey sleeves to a diehard Yankee fan for 10 full years.

On Wednesday, the Sox announced that MassMutual had earned their on-cloth advertising real estate. At the resulting press conference, MassMutual chief Roger Crandall wished failure upon his new partners, claiming a second-place finish to his favorite team, the Yankees, would be his ideal outcome for 2023 and beyond. Love this guy!

Red Sox pick MassMutual as jersey sponsors, MassMutual chief reveals he prefers Yankees

You cannot make this stuff up. I’ve tried! I’ve tried to make up embarrassing stuff about the Red Sox for 20 full years! It’s never been as satisfying as right now, when they’re simply doing all the embarrassing little brother stuff I’d long assumed they’d permanently left behind in September 2004.

Hopefully, this embedded Yankees jersey curse goes better than the time a Boston goon tried to bury a Big Papi jersey in the concrete foundation of the New Yankee Stadium, only to see the Bombers in the World Series in the stadium’s first season in 2009. Nice try! Maybe the real curse was not having the jersey buried in there? Haven’t won one since. Something to think about. Something extremely dumb to think about.

Let’s check in on the Sox players, who surely love the massive patch on their arm bands that now signifies a massive corporation’s undying support of the New York Yankees — oh no!

Jersey changes are coming for us all soon enough. The Yankees hired Legends to seek out their sleeve sponsor for 2023 over the summer, which will hopefully fund Years 6 through 9 of a forthcoming Aaron Judge extension. Ideally, the team will also experiment with a Nike City Connect alternate jersey option in the years to come, which they’ve expressed interest in trying in the past.

This day belongs to Boston, though, who, rumor has it, just changed their rain delay tarp sponsor from L.L. Bean to Timberland. Oops!