Yankees GM Brian Cashman is sleeping outside tonight as part of his yearly campaign through Covenant House to raise awareness for youth homelessness
November 21, 2025
Yankees GM Brian Cashman is sleeping outside tonight as part of his yearly campaign through Covenant House to raise awareness for youth homelessness
48 comments
Brian Cashman asleep at the job, what else is new /s
Gotta say I respect cashman for doing this
It’s unfortunate that these kind souls just don’t have the wealth necessary to help all these young people in need. But they do all they can with the little they have.
“You know, this is a meme: Brian Cashman is asleep on the job. I’ve seen that all over social media.”-Brian Cashman
Needs to do it in late January like a true warrior
What a bum
I respect this, the concrete looks uncomfortable af, hurts my back looking at this.
This is really cool
Wow, this is actually pretty amazing. Good on Cashman 🫡
He’s doing it in November too, not a warmer summer month. I give him props for that.
Actually I respect him for doing this
Good for him – this is the kind of stuff he does and it does gain favor with the media who gives him a pass year after year, which drives me crazt – but he is putting himself out there…I just wish he would quit
This is lovely. It’s way more effective than just trowing some money at it. It gets people talking. Well done.
Westcoast here, I went camping at Wisconsin 3 weeks ago, I thought my feet were going to freeze when it dropped to 27F while watching game 7 of the world series. Idk how homeless people survive on the street come winter time.
Really helping out the meme artists when he does something meme worthy
Now try doing that in January in PA using only a few spare t-shirts as a blanket. (Please don’t do drugs kids I only joke about my past to keep me sane it’s not actually funny)
Good job cashman
Big whoop I do this every night
Nah. Let’s just keep redistributing wealth towards the upper class.
He said he already heard all the jokes about “Cashman sleeping on the job” but that this is still important to do every year.
He’s like a reverse Boras, forcing media to cover him while doing charity work to raise more awareness of the charity, and also he’s answering questions about free agents he’s looking at.
I recall being able to donate specific to his campaign. Can’t seem to find that option this year?
The one time per year I can say that we have the best GM in the game. Back to blind hate tomorrow, sorry Cash.
I legit didn’t know why he always did this

Well shit… that’s a good man.
Fine. Even evil has standards, it seems.
I respect him for doing this. I love that he does it every year, even in the cold and arguably one of his busiest times of the year.
I also find it kind of ironic that a guy making $5 million, negotiating 8 figure salaries is raising awareness for the homeless by sleeping outside.
Not the best GM in the world, but I respect this as someone who has faced homelessness before.
Fuck you, don’t make me appreciate someone who works for the Yankees, how dare you?
Respect and srry for being in the past. I honesty didn’t know he did this
Mem

Man like yea I agree with what you’re doing but fuck me it gets dat at like 5pm what the fuck man?
Good for him but also the meme potential here is fantastic
If george were still alive that’s what he would be doing permanently
Did this in college with Habitat for Humanity in Wisco on a very cold fall night
As a Mariner, I normally hate the Yankees, but I like this.
37°F (3°C) tonight in NYC
Doing this in November mad respect
Don’t post this shit. Some angry Yankee fan is gonna go tickle his feet now.
Well, we all know he’s a bum – good thing he’s finally owning it.
I appreciate him and his dedication to the cause! As a life long redsox fan i salute Brian!
Cashman is sleeping on the sidewalk. George Costanza is sleeping under his desk. What exactly is going on at Yankee Stadium?
Covenant House is a killer charity that’s does a ton of great work for at risk youth. I can’t encourage you all strongly enough to check it out.
Just donated, so apparently it works. Cudos for doing this to bring awareness.
props. he obviously has security making sure nobody messes with them. but also that concrete looks uncomfortable af.
Before his sleazy talk show, Jerry Springer was a news anchor for the NBC affiliate in Cincinnati. He did a series on homelessness and spent a week living on the street to show what conditions were like and what issues homeless people face. He came to our school to give a talk about his experience a few months after that.
Hi r/baseball as a Covenant House employee in the NY who is at this event I want to answer a few questions I am seeing around here.
1. This photo was taken earlier in the day as a press piece for the Sleep Out event hence the lighting.
2. The Sleep Out event itself has been going since around 6-7PM est where sleepers here about Covenant House and the work we do across the world to fight youth homelessness.
3. Current hundreds of people including Cashman are sleeping outside to raise awareness in NYC and around the country.
4. As of now the event has raised over 13 million dollars nationwide tonight and growing.
5. I also want to shout out the Phillies who are hosting CHPA’s Sleep Out in Citizens Bank Park tonight.
6 if you want to get involved check out https://www.sleepout.org/movement
Wait what. Holy shit i never knew he did this. Gained immense respect of him now
48 comments
Brian Cashman asleep at the job, what else is new /s
Gotta say I respect cashman for doing this
It’s unfortunate that these kind souls just don’t have the wealth necessary to help all these young people in need. But they do all they can with the little they have.
“You know, this is a meme: Brian Cashman is asleep on the job. I’ve seen that all over social media.”-Brian Cashman
Needs to do it in late January like a true warrior
What a bum
I respect this, the concrete looks uncomfortable af, hurts my back looking at this.
This is really cool
Wow, this is actually pretty amazing. Good on Cashman 🫡
He’s doing it in November too, not a warmer summer month. I give him props for that.
Actually I respect him for doing this
Good for him – this is the kind of stuff he does and it does gain favor with the media who gives him a pass year after year, which drives me crazt – but he is putting himself out there…I just wish he would quit
This is lovely. It’s way more effective than just trowing some money at it. It gets people talking. Well done.
Westcoast here, I went camping at Wisconsin 3 weeks ago, I thought my feet were going to freeze when it dropped to 27F while watching game 7 of the world series. Idk how homeless people survive on the street come winter time.
Really helping out the meme artists when he does something meme worthy
Now try doing that in January in PA using only a few spare t-shirts as a blanket. (Please don’t do drugs kids I only joke about my past to keep me sane it’s not actually funny)
Good job cashman
Big whoop I do this every night
Nah. Let’s just keep redistributing wealth towards the upper class.
He said he already heard all the jokes about “Cashman sleeping on the job” but that this is still important to do every year.
He’s like a reverse Boras, forcing media to cover him while doing charity work to raise more awareness of the charity, and also he’s answering questions about free agents he’s looking at.
I recall being able to donate specific to his campaign. Can’t seem to find that option this year?
The one time per year I can say that we have the best GM in the game. Back to blind hate tomorrow, sorry Cash.
I legit didn’t know why he always did this

Well shit… that’s a good man.
Fine. Even evil has standards, it seems.
I respect him for doing this. I love that he does it every year, even in the cold and arguably one of his busiest times of the year.
I also find it kind of ironic that a guy making $5 million, negotiating 8 figure salaries is raising awareness for the homeless by sleeping outside.
Not the best GM in the world, but I respect this as someone who has faced homelessness before.
Fuck you, don’t make me appreciate someone who works for the Yankees, how dare you?
Respect and srry for being in the past. I honesty didn’t know he did this
Mem

Man like yea I agree with what you’re doing but fuck me it gets dat at like 5pm what the fuck man?
Good for him but also the meme potential here is fantastic
If george were still alive that’s what he would be doing permanently
Did this in college with Habitat for Humanity in Wisco on a very cold fall night
As a Mariner, I normally hate the Yankees, but I like this.
37°F (3°C) tonight in NYC
Doing this in November mad respect
Don’t post this shit. Some angry Yankee fan is gonna go tickle his feet now.
Well, we all know he’s a bum – good thing he’s finally owning it.
I appreciate him and his dedication to the cause! As a life long redsox fan i salute Brian!
Cashman is sleeping on the sidewalk. George Costanza is sleeping under his desk. What exactly is going on at Yankee Stadium?
Covenant House is a killer charity that’s does a ton of great work for at risk youth. I can’t encourage you all strongly enough to check it out.
http://www.sleepout.org
Just donated, so apparently it works. Cudos for doing this to bring awareness.
props. he obviously has security making sure nobody messes with them. but also that concrete looks uncomfortable af.
Before his sleazy talk show, Jerry Springer was a news anchor for the NBC affiliate in Cincinnati. He did a series on homelessness and spent a week living on the street to show what conditions were like and what issues homeless people face. He came to our school to give a talk about his experience a few months after that.
Hi r/baseball as a Covenant House employee in the NY who is at this event I want to answer a few questions I am seeing around here.
1. This photo was taken earlier in the day as a press piece for the Sleep Out event hence the lighting.
2. The Sleep Out event itself has been going since around 6-7PM est where sleepers here about Covenant House and the work we do across the world to fight youth homelessness.
3. Current hundreds of people including Cashman are sleeping outside to raise awareness in NYC and around the country.
4. As of now the event has raised over 13 million dollars nationwide tonight and growing.
5. I also want to shout out the Phillies who are hosting CHPA’s Sleep Out in Citizens Bank Park tonight.
6 if you want to get involved check out https://www.sleepout.org/movement
Wait what. Holy shit i never knew he did this. Gained immense respect of him now