Caesars Sportsbook, official partner of the New York Knicks, is now open for taking your bets, concurrent with the recent legalization of sports gambling in New York State. An AM New York post touts an NBA jersey promotion, writing:
There are 16 NBA games on the docket for this weekend. Saturday alone features six games, including the New York Knicks, who will be on the road taking on the Boston Celtics. An incredible 10-game slate is set for Sunday, giving bettors even more opportunities to qualify for a free NBA jersey. With this Caesars Sportsbook New York promo, bettors who wager $100+ in cumulative NBA bets with odds of -200 or longer can ultimately earn the NBA jersey of their choice. Once the $100 threshold is met, the user will earn a $150 gift card to the NBA store. This gift card can be used toward the purchase of a jersey.
In his ruling years, former NBA commissioner David Stern was staunchly against the legalization of sports betting. As recently as 2012, Stern joined the other major sports leagues in an effort aimed at thwarting the legalization of sports gambling in New Jersey. When deposed in the lawsuit, Stern said, “The one thing I'm certain of is New Jersey has no idea what it's doing and doesn't care because all it's interested in is making a buck or two, and they don't care that it's at our potential loss.”
Gambling was thought to be a sleazy influence, and more importantly, the leagues couldn’t see how to make much of a buck off of it. By 2014, new commissioner Adam Silver was singing a different song in the New York Times, coming out as the first major sports commissioner to back sports betting. Silver’s last words in that famous op-ed:
I believe that sports betting should be brought out of the underground and into the sunlight where it can be appropriately monitored and regulated.
In 2018, after publicly changing his mind on the issue, David Stern was less lofty and more honest:
I have changed my tune, and I now see it as ‘not negative’ — but only if the leagues receive a fee for their exclusive statistical data.
Now that the NBA is getting its taste, it wants you gambling. This represents a shift of sorts for a product once branded as family entertainment. Washington Wizards owner Ted Leonsis has gone so far as to put a sportsbook inside Capital One Arena, and the Phoenix Suns have done the same at the Footprint Center. In a Boston Globe article titled “By putting a sports book inside his arena, Ted Leonsis thinks he’s created a win-win scenario for pro sports,” the owner says,
It’s not like [sports betting] is Juul, where we created something bad and fooled people on doing it. People were doing [sports betting] and it was inconvenient. I always felt, ‘Imagine if you made it convenient and clean and managed; I bet it will grow the pie, not shrink it.’
The talk of growing the pie and “imagine if you made it convenient” runs contra other NBA messaging on this issue. In recent years, the NBA party line has been that people are going to bet anyway, so you might as well put it out in the open. There’s an element of truth to that, of course, and there’s a solid argument for sports gambling’s broader legalization as a matter of personal liberty and societal transparency. But the NBA and other leagues aren’t doing only that. They’re actively trying to create more gamblers, as we get a glimpse of in the article:
Even if the Wizards or Capitals are playing on weekend nights, Leonsis wants to use the arena’s empty seats in the daytime for patrons to watch the NFL, Premier League soccer, or cricket games broadcast on the arena’s main video screen, with betting kiosks nearby.
He still believes casual bettors need an Apple Genius Bar-type of resource to help them understand the process and make it friendlier. He also concedes that sports books, as well as esports, need to be more welcoming to families, especially women.
Families? What, are they going to open up McDonald's PlayPlaces in the book? Let your five-year-old pick one line for free? I enjoy sports gambling, but any realist understands that this can be a sordid hobby and potentially life-ruining addiction. It’s not a trip to the fucking zoo.
Leonsis tried to draw a contrast to vaping, but I believe it’s fairly comparable. All the happy talk about “clean and managed” betting is very much like vaping’s brand as a cleaner cigarette. But whatever vaping’s downsides, I don’t think many vapes are proselytized as delivering tremendous upsides. This isn’t the case with gambling, where fans are sold a vision of massive wins. And if that’s the case, they should know something: There may be wins, but there is no winning allowed. Why? Because the NBA’s new partners simply won’t allow it to happen.
At the Sloan Sports Analytics Conference, which is part festival and part jobs fair, you’re free to move about from room to room, listening in on whatever panel is taking place. It’s such a casual, breezy atmosphere for a convention devoted to an industry predicated on competition.
Many times, the panel featured a cordial conversation between high-status sports industry types. I once watched two NBA general managers exchange flowery compliments on the Sloan stage. Months later, in a private Summer League setting, one of the GMs asked me why nobody was rightfully ripping the other GM. I felt idiotically scandalized to learn that his performed admiration for a peer had been a farce. But that’s how Sloan was; resentments between rivals were choked down and sublimated for the sake of a giddy convention atmosphere. Then you’d go out at night and hear a GM sneer about Stan Van Gundy’s assumption of coaching and executive duties in Detroit, “Funny how he thinks he can do my job. I wonder what he’d think if I picked up a fucking clipboard and said I could coach!”
One guy did not play by these unspoken rules, though. At Sloan in 2013, I ambled into a ballroom, not expecting much. I’d heard of Haralabos “Bob” Voulgaris, NBA gambler and high-level tweeter, and knew he was on a panel about sports betting. I’d never heard of panel member Matthew Holt, director of race and sports data for Cantor Gaming, but figured that he and Voulgaris would have a friendly conversation, seeing as how they were both in the same industry. Wrong. Voulgaris went at Holt over his statement at a past conference that any player could place a $100,000 to $1 million bet with his company.
Apparently Cantor had cut Bob off from placing a bet, so Voulgaris decided to make a show of that rejection. "I was so excited when I heard that Cantor was going to take $100,000 on NBA bets only to find out they wouldn't take $5,000,” he said. Holt was in an awkward position. While he’d presented his business as open to all comers, he had no real rejoinder to Voulgaris’ assertions. Bob challenged, "How much will you take, Matthew? Let's go to Vegas right now." At one point, Holt said of sports betting, "I don't want to tell people how to build a model," to which Voulgaris interjected, “You don’t know how to build a model."
Bob was a “sharp,” i.e., a successful professional gambler who consistently gains an edge on the sportsbooks via observation and mathematical modeling. Officially, he was allowed to play to his heart’s content, which is why Holt refused to confess his ban. But unofficially, Bob was to be opposed at every turn. It’s common knowledge that the casino might physically expel a consistent winner, but less common knowledge that there’s a digital version of this, applied to sports gaming.
This is how I learned that the game is both winnable and rigged. Indeed it’s rigged because it’s winnable. It’s not easy to beat the book, to be sure. Years after that Sloan standoff, I did a gambling column for a spell at The Athletic and had success, but it quickly turned into a part-time job that I needed to drop. But I can say that winning is doable. Pay attention, observe closely, key in on why the lines might be weak. In another life, I could make my living this way. I fantasized about bumming around near Lake Tahoe, hanging out at the snowcapped sportsbooks, and riding all the action in between hikes through beautiful scenery. Such a life cannot exist, though, as demonstrated by a Twitter user named Spanky.



Spanky, who looks and sounds like a sharp out of central casting, has made a glorious show of his running casino bans around the country. In the above clip, a Freehold Parx casino worker tells him, “You’re not welcome,” and attempts to escort him out, but refuses to tell him what he did wrong. Once outside the casino, the worker reads the following statement:
I’m informing you that you are an undesirable and your continued presence is contrary to the interests of FR Parx, and you must leave the premises and never return. If you refuse to leave or you return, you may be arrested for trespassing.
That’s what winning looks like in this life: Getting treated like vermin, if only pest control happened via the patina of passive aggressive officialdom.
It’s a far cry from how victory is presented to the normie fan. Darren Rovell of the Action Network regularly posts peoples’ massive betting slip wins to his two million Twitter followers. “They don’t let you make $250,000 bets like that unless you’ve established a track record for losing big,” explains “Rick,” a professional bettor. Rick’s an affable recent university grad who turned his collegiate hobby into a career. “Most of my time isn’t spent on getting an edge; it’s spent on figuring out ways to get a bet down.”
This is done through proxies, usually digital, because using an on-the-ground runner like Julia Fox’s character in Uncut Gems happens to be more cinematic than practical. Rick and his small team find ways to outflank the books, but that takes time plus resources. Offshore books are a prime option. Sometimes it’s convenient to use illegal old-school bookies, employing an informal underground industry that includes side-hustling doctors, mafiosos and every character in between. Yes, it still persists outside of Sopranos episodes, despite legalization’s incursions. One reason is that you can get more flexible payment plans.
Of course, these bookies don’t want to take sharp action either. Nobody does. Even Dave Portnoy, founder of populist-pitched Barstool, rejects bets from the savvy at his own sportsbook, analogizing winners to “card counters.” He says, “Try and pick games like normal humans.” As in, try and pick games like a dumb loser.

It’s not like these books are basing these bans on some defined “normal human” standard, though. They just tend to ban big winners. Why so strict, even versus other forms of betting, though?
Voulgaris, who recently came off a run as Director of Quantitative Research and Development for the Dallas Mavericks and has since moved on to crypto endeavors, tells me:
Part of it is in the casino world, the sportsbook is a loss leader, but these online sites, they're not marketing that way because they don't have another business to upsell someone on. It's all online gambling, all online sports betting, versus land gambling.
I once talked to a guy on the business side of sports ventures. One day he met with an executive from the Las Vegas Golden Knights hockey team in a casino. The Knights had carved out a nice slice of revenue that year from one of their ventures, roughly $40 million. “You don’t seem that happy about it,” my guy said. The Knights exec shrugged and gestured towards a roulette table: “This table brought in that much over the same period.”
As Voulgaris puts it:
If you look at what a sportsbook is, you got to walk through everywhere else in the casino. And then, their fear is that if you're gambling at the blackjack table and you're a big pit loser, and now you want to place a sports bet, but you can't, you'll leave and go to a different casino. That's their fear, so they want to keep you there. So it's a loss leader, not just to get you in there, but to keep you there.
As many locales in the United States liberalize their gambling policies, the United Kingdom, where gambling has been freer, has imposed recent safeguards, including a crackdown on advertising. Voulgaris tells a story of using a front who initially bet stupidly in the UK, just to fool the books into letting him bet more.
He just blew through $40,000 right away making the dumbest parlays, and he had to actually have an interview with a counselor before they would let us bet again. That was part of the requirements that the government had it inflicted on these sportsbooks.
The efficacy of such government intervention is debatable, but it is in response to a real issue. Within the liberalized gambling rules, a large population of problem gamblers has sprung up in the UK.
It’s conventional wisdom among educated, cosmopolitan Americans that vice prohibitions are bad and don’t work anyway. The former might be true, but I think the latter is more rationalization than realism. Legalization opens up an activity to a new cohort that otherwise might never encounter it. Also, as you can see from Leonsis’ verbal daydreams, legalization enables large corporations to actively push the addictive activity on the populace.
This will “grow the pie,” as Leonsis says, but, as grows the pie, so too grows the misery. More destitution, divorces, and suicides. This would be the logical result from a large-scale boom in sports gambling. Sure, blame the sucker, but even if we place the responsibility for poor choices on the individual, there should be a recognition of what’s going to happen here, in aggregate. And yes, there’s a cohort, hell, maybe even a vast majority, that harmlessly bets for fun, as most of my friends do. Leonsis’ pie is large.
I’m not arguing that sports gambling should be illegal in most states, though I’m starting to wonder as these leagues quickly shift from “This should be allowed” to “Let’s actively increase its popularity.” What the shift represents is the change from the NBA and other sports from a form of entertainment to something more predatory. There are arguments for spectator sports as an opiate of the masses but I think there’s a better argument for sports gambling, under current rules, as a societal net negative. The fact that they don’t really let you win gives the game away. Leagues have joined forces with something parasitic, apparently glibly, and perhaps heedlessly. I asked the NBA if they knew of any guardrails in place to prevent sports bettors from gambling too much or too often; I did not receive a response.
The NBA has too much going on to worry about some suckers getting in over their skis. In the past, they could perhaps count on the organic growth of their audience. Now, they’re looking to replace dwindling fan populations with bettors in the stands. It’s about the money, obviously, not about allowing “sunlight” into America’s roofed arenas. If it was about sunlight, then the leagues and the books would tell you that you’re not allowed to really win.
It’s always been about profit for the owners, but this is a sea change from pitching sports as a positive, family friendly force. “I love this game,” was a long time ago. The action on the floor has given way to the action off of it. The NBA really wants you gambling now, which means they want you to lose.
Very important column from Ethan that outlines A) the sports leagues want you to *lose* at gambling and the casinos help enforce that, and B) they don't care if you do lose, the more the better in fact.
Are you going to read this at espn.com?? Or The Athletic for that matter?
I'm opposed to sports gambling aside from office superbowl or NCAA $5 brackets because of the ruin it brings to far too many people. That, plus we're guaranteed a Black Sox sized scandal at some point with the gambling money rolling in right now. Some NBA sixth man, looking to make a little side $$ near the end of his career will tank some shots, or an NFL kicker on the way out who figures what the heck, time to shank while I can, are likely candidates for first dibs. Established superstars with gambling problems are next in line, and then we'll see if the NFL and NBA think it was all worth it.
Great piece Ethan. As a UK resident, I’ve always found the relentlessness of ringer/athletic gambling coverage a little mad given their progressive branding.
We have 450 000 kids gambling every week and around 450 suicides per year attributed to gambling addiction. It is every where and largely resented as a parasitical influence. Gambling addiction is no joke and the increasing number of triggers is worrying. Plus the constant ads and betting chat is really dull for non gamblers.