The other day there was a doofus in the boxing class I was teaching (a not uncommon occurrence; to give you a gauge on these numbnuts, one of the most frequent questions I get is,
“Do you know how to box?”).
He came up to me beaming, unpromptedly eager to share his foolproof betting strategy. Apparently you can’t lose as long as you parlay the best receivers on every team to go over their receiving totals. Do the same thing with the running backs, repeat, and collect.
To be honest, he won my sympathy by declaring himself so obviously a sucker. And it warmed my heart even more to hear him say,
“I was just 9 grand in the hole but now I’m climbing out!”
A good way to tell if someone’s a consistent loser is if they’re always giving you tips or telling you about the bets they won.
Honestly, it seems like everybody in my sphere is filching these fucking betting apps for all they’re worth. I’m surprised DraftKings is still in business.
The real sharps though, all you hear from them is woe-is-me this, bad-beat that, but on the low they’re collecting their 54% and up winnings and heading right to the bank.
Listen, if your betting app is giving you boosts all the time—shit the sheer fact that the app is allowing you to still bet—means the algorithm’s pegged you as a loser. So please, spare me.
The proliferation of legal betting is shocking to me because my dad was a lifelong bookie and one of the pioneers of online sports betting; a fact which, if you can believe it, led him to being assiduously persecuted by the United States government for a decade.
My dad, Jon Rogers (aka William J. Caesar), started booking in 6th grade in Toronto, Ohio. An extracurricular interest that led him to finishing 151st out of 154 in his highschool class.
(Many people have described him to me as a “genius”, but he is a testament to the limits of universal genius. Last time I was home, there was a chipmunk in the yard and he said, “what is that?” I said it was a chipmunk. He said, “is it like a tadpole? Does it turn into a Squirrel?”
And of course, there’s the matter of him having been with my mother, a brasilian woman, for 30 years, having visited Brasil dozens of times, having two children that speak fluent portuguese, and yet not knowing a lick of portuguese himself. So, the verdict is still out on his genius.)
That operation evolved into a very lucrative one. So much so, that he got busted by the FBI in 1990. He had a tiny squad of dimwits working out of a knickknack shop in downtown Toronto; the deposition transcripts are honestly hilarious. For their case, the FBI had to prove this guy George Pekins was employee cause they were trying to get my dad with the RICO.
Here’s a brief excerpt of the transcript of the conversation between the lone employee Paul Karr, and the FBI agent:
Q: In your mind was he actually an employee who participated in the business or was he a guy who just hung out?
A: He’s got like a fifth-grade education or something like that. He’s a mongoloid type person, you know. He’s not—he can’t write or nothing.
Q: Does he actually have some kind of mental retardation or?
A: I think so. I’m not positive about it. But you know, I helped him fill out some forms to give to welfare and for the first question the answer was “none” and I wrote it in for him and I was busy at the time and I come back and he just wrote “none” all the way down.
Q: You think he suffers from some kind of emotional or mental impairment?
A: Yeah I guess, he can talk to you sorta normal but, you know, you can tell.
Q: He can’t read or write?
A: He can—scratchy.
Q: He can’t write well?
A: I don’t think he really looks at the paper.
George actually proved very helpful the day of the raid. It was Super Bowl Sunday. George always went to church wearing a big baggy suit. After church, he went over to the shop. My dad was at his house on 1314 Dennis Way hosting a Super Bowl party. He was expecting a raid. He told the guys at the shop: instead of putting the money in the cash register, stuff it in George’s suit. And if the agents bust in, he told George, just walk right out the door. The FBI raided, and he walked right out the door of the shop with 30 grand stuffed in his suit.
While my dad’s dealing with the feds at the house on Dennis Way, he hears a knock on the back door. It’s George.
“I got the money boss!”
“Get the fuck outta here George!”
George made it home safe and they had sufficient money to make the requisite pay-outs. Cause if there’s one thing the customer gotta know it’s that you’re gonna pay.
I tried booking—of course I did. And due to my lack of business acumen and faulty attention to detail, I was not very good. My biggest flub was after I got some new customers; so there was this bookie, C— L—, in town who was fucking horrible, I mean his lines were way outta wack and he’d give you the most ridiculous boosts to entice action: some player might be -120 to score a TD and he’d give it to you for +340. Me and my friend Jacob Decker ran him ragged. After he was broke, he sent me his customers.
These guys were big time idiots and obnoxious to boot. They wanted to do like $10 12-leg player prop parlays. They’d blow up my phone right before kick-off. And cause of that faulty attention to detail, I didn’t even look at what they were, I just assumed they’d lose.
One Sunday around 5pm, this dude texted me, “just confirming i hit that.”
I looked back: indeed he had hit a 12-leg player prop parlay. Fuck. I was gonna have to pay him like $2300 off that $10.
He bested me, but I wasn’t gonna let him win. I paid him $120 and I said, fuck you, if you want the rest, come collect. I cut him off and blocked his number. That’s when I knew I didn’t have it in me. My dad wouldn’t have been dumb enough to book that bet in the first place, but if he did, he would’ve paid that guy every cent.
The FBI tried to pin too much on Jon Rogers and so they lost that case. But he was dead broke. In 1994, two major things happened, he met my mother in Vegas (introduced by their mutual friend, Ron, a frequent felon who just got out of his latest bid in Missouri [I’d rather not say what he was in for] and who was just staying with my parents last month in Steubenville) and he ended up going down to Antigua. Where they’d just passed a law to encourage gambling operations to move down there.
That’s where he opened up Carib Sports. Here is my dad on November 4th, 1996, celebrating his birthday:
(He ate that whole cake, believe it or not.)
By 2001, they had over 2,000 customers, as William J. Caesar said in an interview around that time.
But that turned out to be a significant year, cause after 9/11, they passed the Patriot Act. And deep in the Patriot Act, there was an addendum about the Anti-Terrorist Financing Act.
Long story short, my pops was now a terrorist. So on June 3rd, 2004 (what my dad calls his personal 9/11), as me and my sister were getting ready to go off for first grade, the IRS raided our house on 1314 Dennis Way (how many houses have been raided by two different federal agencies in two different centuries? Can’t be too many.)
Did you know our tax agency has machine guns? My dad never needed any guns to get paid. And if that’s the way you need to collect, you might have a bit of an integrity problem.
The first offer they gave him was 20 years. His big idea was that if he was convicted, between the conviction and the sentencing, he was gonna kill himself, so that we would be able to keep all the money (he heard some Australian guy did it) and so that he could have a win over the government (a pyrrhic victory if there ever was one).
But my mom talked him out of that, and thanks to his resolve and the abilities of country-bumpkin-superstar lawyer Frank Bruzzesse (who finished #1 in his 1974 class at Ohio Northern Law School; #2 was Ben Brafman: Harvey Weinstein and Diddy’s lawyer, who very briefly assisted on my dad’s case until my dad fired him, aghast at his sleaze), Jon Rogers beat the IRS and didn’t do a second in prison.
There’s a lot more to this story obviously, but for more info you’ll have to buy my next book. For now you can check out this podcast:
In conclusion, fuck the government. Fuck DraftKings. Happy birthday, Dad.
Somehow the idea of a chipmunk being a tadpole feels lovely and reassuring
Can't wait for that next book