Caitlyn Cobb and Justin Arnwine discuss women and Black people in poker

Lee Jones
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Posted on: March 29, 2023 11:56 pm EDT

In the first installment of this diptych, I introduced you to D.C.-area poker pros Caitlyn Cobb and Justin Arnwine. Here are the stories of how Caitlyn first started playing poker (and why she took so long to start) and why Justin wears head-to-toe Hello Kitty attire.

Justin Arnwine: In the eight years I played YuGiOh seriously (2003-2011), there were 72 “main events,” just like in the WPT. I was one of just four Black guys who won one of those. Then I got into poker, and I thought, ‘Man, four out of 72 is really good.’ How many Black bracelet winners can you name? Phil Ivey. Tony Gregg. Fortunately, though, Phil Ivey’s name and face was everywhere.

But I didn’t have anybody to show to Caitlyn to say, ‘Yeah, see – this Black woman plays poker.’ I didn’t even know who to show me, but like, Norman Chad and Lon McEachern would always praise all over Ivey, saying he was the absolute best. And nobody would ever dispute it. I mean, the guy that everybody said was the best player in the world is Black.

In YuGiOh, they always said the really good Black players were luckboxes. They didn’t come out and say it was because they were Black that they were dismissing their skill. But it was always there. It was like if you were beating a strategy game and were Black, there was a reason for it besides “being really good.”

Caitlyn Cobb: It was only when Maria Konnikova came on the scene, and said “I didn’t even know how many cards were in a deck.” did I have somebody aspirational to look at. She’s a writer, I’m a writer, and Maria doesn’t seem to be a hustler, which I’m definitely not either.

Just like Maria sweated Erik Seidel, I would watch Justin play, and some of his friends would let me sweat them too. That’s how I learned.

Lee Jones: Blunt question: why are there “no” women, or Black women in poker?

JA: Because there are no examples of success. People gravitate to things where they can see success. Why does anybody buy crypto? Because they know somebody who bought crypto and made money. If you don’t know anybody who made money in crypto, you’re never touching that stuff. Warren Buffett says it’s worthless.

Until you see somebody who looks like you do a Thing, you have no evidence that you can do that Thing.

I think that’s why there are “no” Black women in poker. For the men, yeah, there’s Ivey, but he’s playing tournaments with $25,000 buy-ins. You can have a job and make a great living, but the idea of spending $25k on a poker tournament is absurd.

LJ: Speaking of Atlantic City, Caitlyn, you just went deep at the Borgota, didn’t you?

CC: Yeah, I got tenth in the ladies event. We doubled the guarantee – we got like 180 runners, only three or four men snuck in. It was more runners than they got for the $25k guaranteed at MGM that day.

[Editor’s note: In the two weeks since we had dinner together, Caitlyn shipped a $300 event at MGM National Harbor for over $4300, and Justin finished 5th in a $2200 event at Maryland Live for over $31k.]

JA: Going back to this example idea, when you see Phil Ivey or Tony Gregg playing $10k buy-in events, and your bankroll is $10k, then that means nothing to you. It’s like you hear that Barack graduated from Harvard Law School, and you’re going to community college – what relevance does he have to you, even if he and you are both Black?

LJ: Caitlyn, do you have the idea that, within reason, if you put your mind to something, you can do it?

CC: Yeah. I’ve always thought that I could do anything if I applied myself. They celebrate Kwanzaa in Justin’s house, and one of the days is “Nia,” which means “Purpose.” We were celebrating that day, and talking about how valuable it is to have people around you who believe in you and believe you can succeed. But I’ve always been optimistic about everything.

JA: I’m not religious, but Caitlyn, when she hears that inner monologue, her faith tells her that it’s real – that there’s a bigger plan for her. It’s like Joan of Arc – Caitlyn believes that’s God telling her to go do whatever.

LJ: Caitlyn, is that accurate?

CC: Sort of. It’s not without studying, of course. I mean, faith without works is dead [King James Bible. Jas. 2:26. Ed]. So I can’t just hope I’ll be successful and not do anything. That kind of happened when I was playing the Potomac Winter Poker Open, in which I came in second for $172,000.

I felt locked in with the Universe in some way, as weird as that sounds. Going into my first Day 2, and then my first final table. There was a couple of times during the last two or three tables, I started getting really stressed out, but then a sense of peace just washed over me.

I was having such fun playing against Justin Liberto, and I ended up playing my favorite hand, Q5. Usually when I’m about to play a hand for stacks, I ask myself, “Am I okay going out with this hand?” If the answer is yes, then I do whatever I have to do. But if the answer is no, then I don’t get involved.

I was okay winning with Q5, but I wasn’t really okay with going out with it. I knew I was supposed to fold it, or maybe raise it. The point is, I was supposed to play it differently. And whether I won or not, I knew that I made a mistake playing it the way I did. But that was the only time I went against “the call of the Universe.”

Justin Arnwine discovers that Hello Kitty disarms people

LJ: Justin, you’re legendary for your Hello Kitty attire, and I’m sure you’ve had to tell this story a million times, but would you indulge me with perhaps the abridged version?

JA: I was at Maryland Live, and I’m sure I’d been playing for three or four days. I had a room, but I didn’t have any clothes. So I went to the mall,1 and everything was closed, except the kiosk where they print t-shirts and hoodies. All he had left was three Hello Kitty hoodies, in three different colors in leopard print – I bought all three.

Justin Arnwine with $11,500 in $5 chips, and one of his original Hello Kitty hoodies.
Justin Arnwine, $11,500 in $5 chips. Only $5 chips. And one of his original Hello Kitty hoodies

I came in the first day, it’s all giggles and snickers, but nobody really said anything. The second day, I wore the next one, nobody said anything. Then I went home. And I said, “Well, I don’t need this hoodie, but I bought it, so I might as well wear it.” Blue was my favorite color anyway, so I walk in wearing that one. And one of the dealers said, “Hey, I saw that you’re such a Hello Kitty fan, so I bought you this bracelet.” I put it on, ’cause I didn’t wanna be mean. So I’m playing all day wearing two things. Next thing I know, somebody’s like, “Yeah, I saw you wearing those, so I got you these socks…”

Pretty soon, it became an avalanche. Here’s the thing – the dealers at Maryland Live know me, because I tip really well. The other pros tell me I’m crazy, that I should only tip $1. But I play so tight – I may fold a dealer’s entire down. So when I do win a pot, I try to make up for it.

Anyway, I think people had this Hello Kitty stuff lying around in their house, their kids outgrew it, whatever. So they’d bring it to me. But then this thing happened…

I’d get on the elevator up to my room, late at night. And some White or Asian lady would get on too, just coming back from baccarat, with thousands of dollars in her purse. And I’d think, ‘Here comes the purse clutch, here it comes.’ But then they’d be like, “Oh! You like Hello Kitty?” The purse clutch basically evaporated.

LJ: I am simultaneously heart-warmed and heartbroken.

JA: This has been my experience always, playing in casinos. And remember, my mother is active in civil rights, and she’s given me The Talk, all of it. So the purse clutch was nothing new to me. No purse clutch – now that was new and different. I mean, I don’t expect good things when a police officer walks up to me. But now they’re like, “Hey, my niece is into Hello Kitty.”

I’m not used to a police officer or an Asian lady with thousands of dollars in her purse seeing me as an individual. If an Asian woman wears Hello Kitty, nobody notices. But a Black man wearing Hello Kitty, now I’m an individual, and I’m not confused with every other Black man with dreadlocks.

How Caitlyn Cobb discovered a career and an image

CC: I work hard to be recognized as an individual. Even when I was homeless, whatever job I had, I’d manage to make myself recognized so they’d want to promote me, or give me a better job. In 2020, I formed a Facebook group, and it ended up getting attention from Facebook itself.

I ended up working for Justin’s mom, and I worked for the National Coalition for the Homeless. So when I got into poker, Justin said he thought I could really be an influencer in this space. I’m a writer, so I could write articles.

But there’s this thing: a lot of guys look at you, and they don’t see an individual – they just see a female. So if I don’t want to go on a date with them (and of course, I’m married to Justin now) then I have no value to them.

JA: It was exactly what I went through. People saw me as a generic scary Black man. They were seeing her as a generic female. I said, “I got an idea.” Basically, we constructed her image in the same way we’d construct a 3betting range for her, starting with the tiara. People would have no choice but to see her as an individual, and not just “a female.”

CC: Now that I almost won that PWPO main event, people know who I am. I’m a person – not just a random Black woman, or a potential date. The clothes got me started, but what I’ve done in poker – that’s what’s really made the difference.

Caitlyn, Justin, and I spent over two hours at dinner. I thought I was going to chat with a couple of poker players, but instead, I learned a valuable lesson about the unseen layers of difficulty that come with being homeless. I learned how, if you’re not a White male, you have to find ways to be recognized as an individual, rather than a faceless member of this group or that.

Importantly, I got to know two lovely people a little bit. I certainly came away from the meal feeling richer, and a bit of a better person.

Roll the credits

When Caitlyn told me that she had sung in the middle of the high-limit room at Maryland Live, I told her that, before we parted for the evening, she had to sing, on-camera. She didn’t even blink – gave me one lovely stanza of Amazing Grace, right there in the MGM National Harbor hallway. Enjoy.

Caitlyn Cobb sings Amazing Grace in the halls of the MGM National Harbor Casino/Resort


(1) The Maryland Live! Casino sits across a 50′ wide sidewalk from a huge mall in Hanover, Maryland.