Caitlyn Cobb and Justin Arnwine | Not just another poker couple (Part 1)

Lee Jones poker writer
Lee Jones
Posted on: March 22, 2023 05:07 PDT

I first learned about Caitlyn Cobb and Justin Arnwine from the Thinking Poker Podcast. 1 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 for the conversation that I had with Justin and Caitlyn, we were at a restaurant at the MGM National Harbor Hotel/Casino. Caitlyn was wearing a semi-formal burgundy dress with puffed sleeves, a pink Hello Kitty bomber jacket, and was crowned with a tiara. Justin was wearing a powder blue Hello Kitty hoodie and carrying a Hello Kitty backpack. This sparkly attire figures prominently in the narrative, but we'll get there when the time is right. --Lee Jones

From homeless to poker pro

Lee Jones: Caitlyn, how does your journey to poker and Justin begin?

Caitlyn Cobb: I became homeless 2 around the age of 18 – my adopted mother and I weren’t getting along, so I left – sort of got kicked out. I was living in Glen Burnie, Maryland. But see, there’s an entire community of homeless people – a city under the city – and some people taught me how to survive. Where to sleep, where to go, where not to go. That city under the city is invisible – until you're homeless.

Eventually, I found the Maryland Live! Casino. It was the perfect place – it was warm and sheltered, you could get free coffee, and it was open 24/7. The coffee kept me awake because if they found you sleeping they’d throw you out. They had a coat check room. I could leave my stuff there.
I was going to community college to be a paralegal, and I kind of had to be homeless to attend to school.

LJ:Wait, what?

CC: The social services people in Anne Arundel County had gotten me a place at Sarah House, which is the best homeless shelter in the county. They have a 5:00pm curfew, but I said I couldn’t make that curfew because I had to walk from the college to the bus stop after my classes and then take the bus to the shelter. I couldn’t be there by 5:00pm. They told me I would have to quit my classes. Quit my classes??? School was how I was going to get out of this mess – I’d just have to stay homeless.

LJ:“No shit. So you were spending a lot of time at Maryland Live. That’s how you met Justin?

Caitlyn, the hallucination?

Justin Arnwine: Yeah, so I had a Black Card at Maryland Live. You had to play 5,000 hours of poker to get one, which they thought was impossible. But they didn’t count on insane people, like me. Anyway, April of 2014, I’d been playing for three or four days straight – I’d lost track. And man, it doesn’t matter how focused you stay, or how practiced you are at it, after that long you start to hallucinate.

I figured that I needed to go take a shower--maybe a nap. So I went to the VIP room to ask a host for the room. But there was a guy in front of me who was breaking the unwritten code. See, the unwritten code is that you don’t ask for what you don’t deserve – like if you’re not supposed to get limo service, you don’t ask for it. But he was arguing with them, and there I was, looking at the spiders on the wall or whatever, when Caitlyn--who I don't know--approaches me.”

CC: The guy who was arguing with the host was a friend of mine, and I knew he’d try to just wear them down – it could be a while. So, I went over to Justin, and said, "Hi – you may have a long wait – that friend of mine is awfully persistent."

JA: So, there’s this Good Samaritan, who, of course, might also be a hallucination, telling me to be patient. But we got to talking. I asked her what she liked to do. She said she liked to sing. I said, "Play me some of the songs you like on your phone." She said she didn’t have any songs on her phone. Well, I’d been up for 95 hours, so I just said right out, "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 sure, let’s have fun with this hallucination…”

CC: Well, I just stood there and sang Amazing Grace in front of all the people in the high-limit room.

JA: The lady betting chocolate ($5,000) chips turns to watch the performance. I thought this girl was very cool. But I was kinda thrown off by her outfit. See, I went to private school, and there’s a lot of rich girls that like to dress poor. It has an actual name: "slumming down." And that’s how she was dressed. So I figured she was either extremely rich or extremely poor. But I didn’t want to judge a book by its cover – I’m sure I looked insane to her. Shells in my braids…

LJ: Shells?

JA: I mean, who am I to judge? I looked nuts. I told her I played poker, and she believed me. But I went ahead and said, "Look, here’s my phone number. If you get tired of your friend’s shenanigans, give me a call. You can come up to the room and hang out."

The reason I gave her my phone number, was because – well, I still wasn’t completely sure she was real, and I had no interest in getting a phone number from an imaginary person.

I’d had a lot of experience up in New Jersey where I’d be up 72 hours at a stretch. I knew how to fade the hallucinations. Like, I’d only get red chips. I’d never color up. That way, I couldn’t misclick and accidentally bet $500 when I meant to bet $25.

CC: Yeah, so I called him that night and said I was tired of this guy, and did Justin get that room? He did, so I went up there and we hung out.

LJ: “Best meeting story of all time. Justin, you mentioned Atlantic City. Can you tell us more about how you became a semi-homeless AC grinder?

No Home Jerome 2.0

JA: My mom is a pretty famous civil rights lawyer. 3 I had been playing this card game YuGiOh real seriously, and some of my buddies in that told me about poker. See, I’d played poker just a few times before. One time, it was with my mom – I think we played seven-card stud. She beat me out of my allowance, and wouldn’t give it back to me…

LJ: Cold…

JA: She was extremely anti-gambling, and she thought of poker as just gambling. I think her intent was to cure me of gambling, and it worked for years. She literally called it "enabling" if I was gonna live in her fancy mini-mansion but play poker. She just wanted me to get over this poker thing sooner than later. But I decided that I was going to make it work.

That’s how I became a homeless guy grinding in Atlantic City. I’d take the bus up there during the week – this was long before Maryland Live or MGM opened – and the rooms were $60 per night. Except on the weekends when they’d be $365 per night. I wasn’t having any of that, so I’d play all during the week, get a late checkout on Thursday, and then say, "Well, I get a place to stay on Monday. Until then, I can play, or sleep on a bench, or whatever." That’s how I got good at playing non-stop for multiple days. That’s also when I learned to play through the hallucinations. I’d think, "Whatever I’m seeing over there isn’t real, so just ignore it and play my hand."

And this is how I got good at tournaments. I’d go up on the bus with $300 – sometimes less – and the minimum buy-in at the $1/2 game was $60. So, I’d think, "Okay, I got five buy-ins." Now, that’s 30 big blinds, right? But why in the world would I put $100 on the table when I could get in for $60? And when you’re sitting on 30 bigs, you learn real quickly you can’t be playing any ten-eight suited. I've got more hours playing 30 bigs than most tournament players.

But speaking of tournaments: the first tournament I ever played was the Borgota Winter Open. It was supposed to be a two-day tournament, but at the end of Day 1, they said, "We’re just going to play it out." Which, they were the Borgota, and nobody said anything, so I figured this happened all the time.

We got down to three-handed, and I was having a different kind of hallucinations. I got ace-king, but I wasn’t sure I really had ace-king – I must have looked at that hand 20 times. But eventually, I persuaded myself that it was indeed ace-king, and I ripped it in there. The other guy--I think all this card rechecking I did made him believe I really didn’t have a hand--called. And got there.

But man, I was done with tournaments. I didn’t play another tournament until the Maryland Live people, who I trust, told me they wouldn’t do anything like that.

One big family

LJ: So tell me how Caitlyn came to live at your house with your mom and grandmother.

JA: First off, it was quite a while before Caitlyn told me she was homeless. By the time she told me, I already liked her and didn't care. And maybe I had a little better understanding of her situation. After all, when I was up there grinding in Atlantic City, a lot of people thought I was homeless. And they looked at me real differently when they knew – or didn't know – who my mom was. So, I got it.

But Caitlin was having to travel between Glen Burnie and Maryland Live. Sometimes walking, sometimes hitchhiking. Sometimes she's been awake all night. She's been running good, but if she continues on this path, I knew there were just too many ways things could go south.

Originally, I wanted her to finish school before she moved into my family's house. But I wasn't sure she would finish school if she stayed homeless. And I sure didn't want to read about her in the news. So, I talked with my mom and grandmother, and she came to stay with us.

At the time she came to live with us, she didn't play poker. I mean, until she got glasses, she could be sitting here with the board there (indicates a spot two feet away on the restaurant table), and she couldn't tell between the queen of hearts, the queen of diamonds, or the jack of hearts.

She used to sit behind me and watch me play. One of the only Omaha tournaments I ever played – the Poker Players Championship – I won. The last hand, she didn't even know I had won. I had a set of fours, the dealer is pushing the pot to me, and the TD came over to shake my hand.

Caitlyn said, "Who won? You or her?"

LJ: So you got to an ophthalmologist?

CC: Yeah, I got to the ophthalmologist, and she said, "I can give you 20/20 vision." I was all, "What?" And it turns out I'm kinda color-blind, even though that's usually in men.

That's why it took me so long to start playing. I'd sit and watch Justin play for hours, and people would say, "When are you going to start playing?"

Coming In Part 2: Caitlyn's journey from the rail to the table, and Justin's journey to becoming a walking Hello Kitty advertisement.


(1) You owe it to yourself to listen to the full audio podcasts – think of this piece as a trailer for them. Also, if you didn't know about the Thinking Poker Podcast before... you're welcome. The the titles below are clickable links.

Caitlyn Cobb interview
Justin Arnwine interview , part 1
Justin Arnwine interview, part 2

(2) There is a debate over the use of the word "homeless." I believe it's vital to be sensitive to how an individual wants to be addressed (particularly personal pronouns). But homelessness, whatever you call it, is such a blight on our entire society that I don't want to take our eye off the ball for a single moment to argue vocabulary. Here is a good summary of my feelings about "homeless" vocabulary and semantics.

(3) This is a gross understatement. Barbara Arnwine is a legendary civil rights lawyer. You can (and probably should) read more about her.