I first learned about Caitlyn Cobb and Justin Arnwine from the Thinking Poker podcast. Serendipitously, I was already planning a trip to the Washington, D.C. area, so I arranged to have dinner with them — their stories deserve to be told in as many places as possible.
To set the stage: we met at a restaurant inside the MGM National Harbor Hotel & Casino. Caitlyn was wearing a semi-formal burgundy dress with puffed sleeves, a pink Hello Kitty bomber jacket, and a tiara. Justin had on a powder blue Hello Kitty hoodie and carried a matching backpack. That sparkly attire will factor into the narrative, but we’ll get there when the time is right.
From Homeless to Poker Pro
Lee Jones: Caitlyn, how did your journey into poker—and meeting Justin—begin?
Caitlyn Cobb: I became homeless around the age of 18. My adopted mother and I weren’t getting along, so I left—or rather, I got kicked out. I was living in Glen Burnie, Maryland. But there’s an entire community of homeless people, a city under the city. Some of them taught me how to survive—where to sleep, where to go, and where not to go. It’s invisible—until you’re part of it.
Eventually, I found the Maryland Live! Casino. It was perfect—warm, sheltered, open 24/7, and they had free coffee. The coffee helped me stay awake, because if they caught you sleeping, they’d throw you out. They had a coat check room, too, where I could leave my stuff.
I was attending community college, studying to become a paralegal. And weird as it sounds, I kind of had to stay homeless to keep going to school.
LJ: Wait, what?
CC: Social services in Anne Arundel County got me a place at Sarah’s House—it’s the best shelter in the county. But they had a 5:00 p.m. curfew. I couldn’t make it back in time after college; I had to walk to the bus stop after classes, take the bus, and still get to the shelter. They told me I’d have to quit school. But quitting wasn’t an option—school was how I was going to get out of that situation. So I stayed homeless.
LJ: “No shit. So you were spending a lot of time at Maryland Live. Is that how you met Justin?”
Caitlyn, the Hallucination?
Justin Arnwine: Yeah. I had a Black Card at Maryland Live. You had to log 5,000 hours of poker to get one—something they thought was impossible. But they didn’t count on maniacs like me. This was April 2014. I’d been playing for three or four days straight—lost track. After that long, no matter how practiced you are, you start to hallucinate.
I went to the VIP room to ask for a shower and maybe a nap. But some guy ahead of me was arguing with the host—breaking the unwritten code. See, you don’t ask for stuff you don’t qualify for. This guy was doing just that. I was half out of my mind—seeing spiders on the wall or whatever—when Caitlyn approached me.
CC: The guy arguing was a friend of mine. He could be really persistent, so I figured we’d be there a while. I went up to Justin and said, “Hi — you might have a long wait. My friend’s not going to let this go anytime soon.”
JA: So here’s this Good Samaritan—who I thought might just be a hallucination—telling me to be patient. We got to talking. I asked her what music she liked. She said she liked to sing. I asked her to play something from her phone, and she said she didn’t have any songs on it. I’d been awake for 95 hours, so I said, “Yeah, you’re not a singer.”
She said, “I’ll sing to you right now.” And I’m thinking, “Okay, now I know you’re not real. But let’s go with it…”
CC: So I just stood there and sang Amazing Grace—right there in the high-limit room.
JA: There’s a lady betting $5,000 chips turning to watch her. I thought Caitlyn was really cool, but I couldn’t figure out her outfit. I’d gone to private school—there are rich girls who like to dress poor. It’s called “slumming down.” She looked either extremely rich or extremely poor. But I didn’t want to judge—especially not looking like I did, with shells in my braids…
LJ: Shells?
JA: Yeah, I looked crazy. So I gave her my number. Told her, “If you get tired of your friend’s antics, hit me up—you can come hang out.”
I wasn’t even sure she was real. But I figured: if she was, and I didn’t give her my number, I’d regret it. If she wasn’t, I wasn’t gonna waste time getting a fake number from a hallucination.
That was something I learned grinding in Jersey—playing for 72 hours straight. I knew how to work through hallucinations. I’d only use red chips—never color up. That way, if I lost my grip, I couldn’t accidentally bet $500 instead of $25.
CC: I called him that night. Told him I was tired of my friend and asked if he’d gotten that room. He had. So I went up and we hung out.
LJ: That’s one of the best meeting stories I’ve ever heard. Justin, you mentioned Atlantic City—tell me more about becoming a semi-homeless grinder.
No Home Jerome 2.0
JA: My mom’s a well-known civil rights lawyer. I was into Yu-Gi-Oh growing up, and some friends from that world introduced me to poker. My mom and I had played poker once—seven-card stud. She beat me and kept my allowance.
LJ: Brutal.
JA: She was extremely anti-gambling. To her, poker was just gambling. She wanted me to drop it entirely. Living in her house and playing poker? That was “enabling,” in her view.
So I left and went to grind in Atlantic City. Rooms cost $60 on weekdays, but $365 on weekends. No way I was paying that. I’d go Monday through Thursday, get a late checkout, and then play or sleep on benches until Monday rolled around again.
That’s when I learned how to play through anything. No sleep? Hallucinations? Just focus on your hand.
I’d go up there with $300—or sometimes less. The $1/$2 game had a $60 buy-in. So I’d think, “Cool, five buy-ins.” I’d never buy in for more than the minimum—what’s the point? That’s 30 big blinds. And when you’re playing short-stacked, you learn quickly—you can’t be out here with ten-eight suited. I got more hours on 30 bigs than most tournament players.
My first tournament was at the Borgata Winter Open. Supposed to be two days, but they just said, “We’re playing it out.” Nobody objected, so I assumed that’s how things worked.
We got down to three-handed, and I had Ace-King—but I wasn’t sure I really had Ace-King. I kept checking my cards like 20 times. Eventually I convinced myself, jammed it, and lost. After that, I was done with tournaments—for a long while.
One Big Family
LJ: So how did Caitlyn end up living with you, your mom, and your grandmother?
JA: It was a while before she told me she was homeless. But when she did, I already liked her. I didn’t care. And I kind of got it. When I was grinding in AC, people assumed I was homeless. And they treated me differently once they knew—or didn’t know—who my mom was.
She was going between Glen Burnie and Maryland Live. Sometimes walking. Sometimes hitchhiking. Sometimes awake for days. I thought: if she keeps this up, things could go really bad.
At first, I wanted her to finish school before moving in. But I realized—if she stayed homeless, she might never finish. And I didn’t want to read about her in the news one day. So I talked to my mom and grandmother, and she came to live with us.
At that point, she didn’t even play poker. I mean, she didn’t even have glasses yet—she could barely see the board. She’d sit behind me and just watch me play. One of the first times she did that, I won the Poker Players Championship—one of the few Omaha tournaments I’ve ever played. The final hand…
(To be continued in Part 2)
