Beyond The Outrage: A Closer Look At The DraftKings VIP Lawsuit Raising Sports Betting Alarm Bells

I am not wise. I may be smart — thank you very much — but “wise”? No. Not me.

The running joke in my house is that if reincarnation is a real thing, I’m on my third or fourth go-around, whereas my wife is a bodhisattva, on life bajillion, only sticking around this plane of existence on her way to nirvana to make sure I don’t trade the family cow for a handful of beans.

But with age comes a dollop of wisdom. (Probably osmosis.)

And one of my most wisdom-y notions is simply this: It’s never black and white. It’s always gray.

Now, some shades of gray may be bordering on midnight black or blinding white, but there’s always — always — at minimum, a hint of that gray. (Every silver lining, etc.)

This notion came to mind as I read through the bombshell lawsuit against DraftKings that dropped last Friday in New Jersey (full complaint available here). 

And what a bombshell it is: Lisa D’Alessandro is claiming her estranged husband (noted in the lawsuit by his DK username, “Mdallo1990”) racked up nearly $1 million in gambling losses on DraftKings Sportsbook between 2020-2024, stealing from her credit cards and their children’s savings accounts to fund his habit. The numbers are admittedly staggering — he went from betting less than $4K a month to $125K monthly, all on a $175K-a-year salary. DraftKings allegedly responded by showering him with VIP perks and vacation offers instead of checking where the money was coming from or offering help. According to the suit, they watched his addiction spiral while keeping the incentives flowing, even though his betting volume should have made it clear something wasn’t adding up. (DraftKings did not respond to a request for comment on Monday about the lawsuit or the underlying allegations.)

This looks ugly, make no mistake, and there was no shortage of outrage on the social media site known as X.

Clearly, this is 100-0 in favor of the plaintiff. DraftKings is guilty, the VIP hosts are guilty, burn it all down.

Or maybe not?

But is it possible that maybe it’s 80-20 here? Or 70-30? I mean, some may go as far to say 50-50. Or even … gasp! … it’s not DraftKings’ fault?

There are people out there who see it that way. 

And honestly, that tweet above makes some sense. Look at brokerage houses and their enticements to get you to sign up to trade stocks. If I do that and then lose my five-figure fortune gambling in the stock market, should they be held accountable for my actions?

I have the McDonald’s app downloaded on my phone; should I file a lawsuit if I eat that grease every day and balloon to 400 pounds because they keep offering me free French fries?

You see where I’m going with this. 

That’s a little bit of the gray right there. Personal responsibility, pure and simple. That’s not to say problem gambling isn’t a thing. Obviously, there are people out there who cannot control their gambling behavior and need help. This guy may be one of them. He also may not. We don’t know. All we do know is problem gambling is not a one-size-fits-all issue. Your problem gambling may very literally be my day at the races.

Anyway, here’s more gray:

According to the lawsuit, Mdallo1990 wagered over $12.5 million in a four-year span, and lost a little over $940K. That’s not good, but it’s also, in some regards, not exactly terrible. It’s a 7.5% hold for DraftKings, but then add in all the free bets and deposit bonuses and whatnot he was given as a VIP (from the suit: “Defendants provided Mdallo1990 with Onyx Elite level status and rewards in 2022 and 2023, which included, but was not limited to a suite of high-end Apple products [and] options for a vacation paid for by Draft Kings”) and that number goes down. Let’s call it 5%, maybe 6%. 

So it’s not like this guy was a huge loser; he was, more or less, #OneOfUs.

Theft: When, where, why

And nowhere in the complaint do we find out when those losses — and his stealing of his wife and kids’ money — occurred. In short: We don’t know if he was profitable and then went off the cliff at the end, or if he was chasing losses from the beginning. All it says in the complaint is, “Mdallo1990 stole money from his spouse, the Plaintiff Lisa D’Alessandro, to deposit with the Defendants including, but not limited to, stealing money from her credit card(s) and taking money from other accounts without her permission or knowledge” and, later, that he stole money from both his children, money that was “funded exclusively with gifts from baptism, Christmas presents, and birthday presents.”

He is accused of stealing it, but there is no timeline. Was this the end game of a desperate man, or did he start his whole gambling adventure by ripping his family off? Maybe the plaintiff’s attorney is not yet showing all his cards.

This does not absolve DraftKings, but just adds to the gray. After all, if he was winning most of the time … well, I didn’t come up with the line, but it’s not problem gambling if you’re winning, right? Isn’t that a cousin of Charles Barkley’s infamous quote, “I don’t consider it a problem because I can afford to gamble”?

Then there’s this: We don’t know how much, how often, or if at all he was making withdrawals. Was he just playing until he hit zero, and then re-upped? Or was he consistently banking his profits, and then going back in? 

We also don’t know how much money he stole from his wife and kids. It doesn’t say. But using some logic (dangerous game), how much in baptism and birthday money could there have been, and how many of his wife’s credit cards could he have maxed out? Make no mistake — if true, this is scumbaggery at its finest. But we’re talking, what, maybe a hundred grand? Two hundred grand? Certainly not enough, I would think, to cover the $12.5 million in deposits, and the guy’s salary — $175K a year, according to the suit — also wouldn’t cover it. 

Which (I think) (probably) means he was routinely withdrawing and depositing money, which would (maybe) indicate the real problem didn’t come until the end, when the horse was out of the barn.

Or as Ernest Hemingway put it in The Sun Also Rises: “How did you go bankrupt?” Bill asked. “Two ways,” Mike said. “Gradually and then suddenly.”

But we don’t know. The reason we don’t know? Too many missing details, too much gray area.

More gray? Sure, why not 

We don’t know yet what the VIP hosts said or did with the guy, how frequently they communicated, and we don’t know what the guy said or did with the hosts. Maybe there were conversations back and forth about his play. Maybe he showed them he had $10 million in the bank, and maybe it was a fabrication. Maybe, maybe, maybe. We don’t know. 

Right now, the only word we have is via a (probably and rightfully) pissed off soon-to-be ex-spouse.

Listen: We may come to find out DraftKings is the devil, sports betting is ruining the country, VIP programs need to die, and all the pitchforks and torches are necessary. But for now?

We don’t know. Too much — way too much — gray.