New York Yankees general manager Brian Cashman partakes in plenty of annual events, but none more unique than Covenant House's "Sleep Out" charity, during which he sleeps outside, on the concrete ground in Manhattan on a cold November night.
It's a nice thing. The charity raises awareness and money for homelessness, which is a heartbreaking and ongoing problem in New York City.
But, as you know, doing something like this is bound to expose oneself to jokes on social media. Some particularly ruthless Yankees fans have used the images of Cashman in a sleeping bag, bundled up to his chin, as a symbol of his perceived inactivity during most offseasons.
Cashman is far from an inactive GM. But he's left a lot left to be desired ever since the Aaron Judge era began (and perhaps a few years before that). So, as you can imagine, the jokes have gone over the top.
For those of you posting them annually ... just know Cashman is watching. And he proved that with his recent comments last week at the Covenant House charity event. He sees your "mems"!
Brian Cashman gets into his sleeping bag for the Covenant House Sleep Out
— Yankees Videos (@snyyankees) November 21, 2025
"You know this is a meme about Brian Cashman is asleep on the job, not doing his job, seen that all over social media" 😂 pic.twitter.com/QL5304FR7A
Brian Cashman has funny callout for Yankees fans at annual charity event
It only would've been more boomer if he'd called it a "me-me".
Nonetheless, Cashman's keen attention to social media is something we've long suspected, considering the Yankees seem to go against the grain every offseason and trade deadline, deviating from the online conversation and fan discourse. Outside of the Giancarlo Stanton trade and Gerrit Cole mega contract — moves that were followed by less spending and fewer impact additions — you cannot identify any other franchise altering decisions he's made for the long haul. Most have either been bad (go ahead, name one) or are too early to make a call on (Max Fried, Jazz Chisholm).
Perhaps the best approach for Yankees fans in the forthcoming offseasons is to ... remain less terminally online. You know who you are. The "PLAYER Enjoyer" accounts posting about every single possible trade candidate, no matter how unrealistic, and deeming it a complete failure if the Yankees don't pull it off. Go hibernate for the winter. Hit the treadmill. Try meditation. The less we speak, the more likely it is Cashman is more inclined to execute the moves that actually make sense and resonate with the fanbase.
It's at least worth an experiment. Just relax on the mems for now, because we need a productive offseason to salvage Judge's prime.
