I set out to write a story about fashion in the sports betting world. Mostly because I could only think of three guys in the public sphere within the industry who had anything resembling their own style: Dave Sharapan, Roxy Roxborough, and Bill Krackomberger.
And honestly, what tickled me the most was the Twitter/X-love affair between Sharapan and proprietor of the Super 70s Sports handle, Ricky Cobb. Sharapan — along with his trademark look of a baseball cap and jersey — has brought Cobb’s T-shirts into the mix. As a result, he’s gotten the highest praise Cobb can give, repeatedly calling Sharapan — and again, this is high, high praise — a “sweet bastard.”
Yes. That’s the story I set out to write.
And I’m going to tell that story. It’s in here.
But there’s also a second, accidental story that came out of my conversations with this fashionisto trio.
And that one has to do with grandfathers. Who knew?
One sweet bastard
Sharapan, the “Sportsbook Consigliere,” dresses like he hired George Clooney and Brad Pitt to rob the entire Pittsburgh Pirates merch store. Flat-brimmed baseball caps. Endless jerseys. The guy is swimming in sports apparel.
“I’ve always loved the gear from the time I was a kid,” Sharapan told InGame. “There was a [sporting goods] store in Pittsburgh, called Honus Wagner. My grandfather ended up working there, and it was right around the corner from my dad’s store. So it was a big treat to go down there, to see my grandfather, to get some gear. They had everything.”
Sharapan’s collection is meticulously organized — by sport, by division, by team.
“I have 38 Pittsburgh Pirates hats,” he said, before revealing his system. “They’re organized by sports and by division. All my NL East hats are in one area. All my NL Central hats are in another area. And so on.”
Not everyone in the Sharapan household buys into his fashion choices.
“My wife loves the curved brim,” he said. “And if she gets a hold of a hat, then it becomes curved.”
And then there are the Super 70s Sports shirts — the ones that earned him the “sweet bastard” moniker from Cobb. These became part of the Sharapan brand after he fell deep into the nostalgic rabbit hole of Cobb’s Twitter feed.
“I love Ricky’s Twitter feed. It’s great,” Sharapan said. “So many of us from that time range, this age … I mean the guy brings joy to my life every day.”
That “joy” resulted in what can only be described as digital shopping tilt.
The shirts now bring almost as much attention as the hats.
“I get a comment every single time,” he said.
Who knew being a “sweet bastard” could be so rewarding?
Bow ties to order
If Sharapan is “the hat guy,” then Roxborough is “the bow tie guy.” The legendary oddsmaker often looks like he would’ve been right at home at Jay Gatsby’s parties.
In fact, Roxborough’s fashion sense stretches back that far.
“I never saw my grandfather when he didn’t have a suit and a tie on,” Roxborough said. “I mean never. Absolutely never. He just never came out of his bedroom unless he had on a suit and tie. And my father wore a suit and tie, I would say six days every week except Sunday, and on Sunday we had to wear sports jackets to dinner.”
This formality carried over when Warren Nelson, the owner of the Cal Neva, gave young Roxborough — about 30, and selling lines to Nevada sportsbooks for the first time — a fashion reality check.
“He told me, ‘You can’t be looking like a hippie. You got to look the part,’” Roxborough recalled.
Goodbye tie-dye, hello ties, in other words.
Roxborough’s fashion saga continued when he met his wife of 25 years, Alise, a fashion designer who apparently decided her husband needed a colorful makeover.
“Everything changed,” Roxborough said. “She just started putting colors together. She’s made a lot of my clothes. She designed them all. She’s sewn some, and others she sends out to a tailor. And she makes my bow ties. I never wear one that I bought at a store.”
As for the fedora he’s often sporting?
“I started adding the hat. I don’t know why. It just looked like a Las Vegas look anyway,” he said.
These days, retirement has given Roxborough license to go full peacock.
“I can go to colors you could never wear if you’re working,” he said. “I can wear racetrack clothes every day.”
The Kangol king
And then there’s Krackomberger, a professional sports bettor. And while you can spell “Krackomberger” without all the letters in “Kangol,” it’s damn close.
While Roxborough goes for the rainbow and Sharapan dresses like a walking sports memorabilia shop, Krackomberger keeps it simpler: black, blue, and — always — a Kangol.
“I’ve been wearing Kangol hats for over 25 years,” he said.
As to the “why?” Enter Grandpa.
“My grandfather wore hats every day. He wore a fedora every single day,” Krackomberger explained. “They lived in north Jersey, in Perth Amboy, and he wore a hat and would not leave the house without a hat. So I always loved hats just from my grandfather.”
As for his Kangols, specifically?
“The old milkmen and the old newspaper boys, they wore hats like this,” he said.
His hat obsession got a boost after his first ESPN appearance on Cold Pizza.
“Someone from Kangol reached out to my brother somehow,” he remembered. “They sent me a box of hats 20-some years ago. And that was that.”
But Krackomberger isn’t your average fashion influencer, happy to wear anything that’s free.
“They didn’t realize that all I wear is black and blue,” he said. “Dark black and dark blue, in fact. I gave away the pinks, the yellows.”
As to why the dark colors, and just two of them at that?
“I feel more comfortable in darker colors. I don’t want to walk around like a freaking parade float,” he said. “I’m going to stand out in a crowd with the hat. I’m not looking to stand out more.”
The grandfather effect
I’m a pretty frugal guy, at heart. I don’t necessarily need to be.
Every car I’ve ever owned was A) used and B) driven until the death of the car. Not a metaphorical death. Literally “tow it to the junkyard” death.
My home is 1,600 square feet. My wife and I could afford to buy a bigger house, but … nope. It’s fine. It’s almost paid off. Good enough. Wish we had a toilet downstairs, but whatever.
I’m a coupon clipper. I’m an online casino bonus hound. I like ordering off the happy hour menu. I get genuinely excited when peanut butter goes on sale, even if I never bought the brand before.
I could go on, but you get the picture.
Why am I like this? It doesn’t track. I grew up in north Jersey, upper-middle class, never wanted for a thing. I have friends I grew up with — still friends to this day — who had similar socio-economic backgrounds. They make twice as much money as me and live paycheck to paycheck. They drive BMWs. I drive a car that keeps me mostly dry when it rains.
So what gives?
Well, my grandpa died when I was 14. He was 90-something. He was first-generation from Russia, became a dentist, bought some apartment buildings, lived a good life. Always — always — had a wad of cash in his pocket. Like a gas station attendant.
He was born in 1895. In 1935, thick of the Great Depression, he was 40 years old, two kids, a third coming later. He learned the value of a dollar. He learned the value of a penny, for that matter.
When I was a kid, on more than one occasion, he’d grab me by my forearm and tell me to never buy anything on credit, ever. If I didn’t have the money in hand, I couldn’t afford it. Pretty simple life advice from a guy who lived through some not-simple times.
And sure, while I do have a mortgage — no getting around that — I have never carried a credit card balance. If I don’t have the cash, I don’t buy it. Grandpa would be proud.
When I mentioned the grandfather connection to Krackomberger, his response was like I’d just told him the secret to consistently hitting 16-leg parlays.
“I didn’t think of him or it until you asked me the question,” he said. “Wait until I tell my wife. That’s exactly right. My grandfather wore hats all through the 20s and 30s. He was born in 1910, my grandfather. And I was very, very close to him.”
As our conversation concluded, Krackomberger dropped this gem: “I still have some of his hats in my house.” The man keeps vintage grandfather hats as keepsakes. If that doesn’t perfectly — wait for it — cap this story, I don’t know what does.
So there you have it. Three men. Three completely different styles. All apparently getting their fashion sense directly from Grandpa’s DNA. I didn’t see that plot twist coming, and neither did they.
I relayed all this to my father, who’s turning 85 this June. I’ve got a son, just turned 16.
“Any wisdom you’ve got, impart on the boy,” I told him the other day. “Apparently, people listen to their grandfathers.”
He nodded, said OK.
I continued.
“Because lord knows he’s not listening to one word that comes out of my mouth,” I said. “And, shit, I can’t remember one thing you taught me.”
Fathers serve as guideposts and prison guards for their sons; grandfathers, as it turns out, serve as rabbis, senseis, gurus, and — clearly — fashion icons.
