Until the letter arrived, Ike Lee thought he had sports betting in Connecticut largely figured out.
He would bet tirelessly at off-track betting locations in New Haven, where he is a Yale medical student, capitalizing on statistical insights and slow-moving betting lines to make thousands of dollars in a game inherently slanted against bettors. When he wanted to place larger wagers, he'd drive to one of the state's tribal casinos, where betting limits were higher. He befriended employees at the various sites, studied the mechanics of the kiosks he used and embraced the puzzle of predicting sports outcomes.
Lee, 29, didn't consider himself a sports fan and rarely bothered to watch the games he'd bet on, but he could recite stats about mid-major college football teams and reel off players on Korean Baseball Organization rosters. He was hyper-competitive and willing to pursue any advantage — and saw those traits as a secret to his success.
Then, in late May, came the letter, a single-page from the Connecticut Lottery informing him he'd been banned from wagering at off-track betting sites statewide, making him one of only five people in the state on a special list of "prohibited patrons." Just like that, his days betting the way he liked to were over.
"From my perspective it was pretty much out of the blue," Lee says.
The lottery, as explained in the letter, says Lee broke rules and can't be allowed to wager further. Lee says he was never informed of the rules in question and that he's been banned at least in part because he was making too much money from betting. A lottery official says that line of argument sounds like "sour grapes."
Lee has hired a lawyer and is currently in the midst of an appeals process that appears to be the first of its kind since Connecticut legalized sports betting. It's the type of drama that likely wasn't front of mind when legislators voted last year to legalize sports betting but that inevitably comes with authorized gambling.
For someone who bets as much as he does, and who is fighting so hard for his right to continue, Lee says he's uneasy about gambling's role in society, especially now that it is authorized in so many places. He wonders what value the games really provide the state of Connecticut. He questions the state's ability to properly manage sports betting. And he struggles with his role in what he considers a morally questionable industry.
Though Lee believes he could make a healthy living on sports betting, for now he plans to graduate medical school and become a doctor.
"For all intents and purchases, I am a leech on the system," he said of his sports betting exploits. "I don't generate any social value for anyone involved anywhere. This is the most selfish professional thing I have ever been involved with, and that doesn't sit well with me."
As Lee sees it, his story is about more than just his personal ability to wager. It's about thorny questions that sports betting continues to raise in Connecticut and beyond. Who wins and loses from legal gambling? Who gets to decide? And what exactly have states like ours gotten themselves into?
Ike Lee isn't like most people who bet on sports.
Most people who bet on sports do so casually, placing a wager here or there, often just for fun. Lee does so with purpose, precision and research, seizing on fluctuations in betting odds that few others even notice.
Most people who bet on sports lose money, if not in the short term then certainly in the long-term. Lee says he has made thousands of dollars in the year since Connecticut legalized sports gambling and that betting has helped pay off his student debt.
Most people who bet on sports wager on teams and games they care about and plan to watch. Lee says he doesn't particularly like sports or care who wins.
"I'm not a sports fan," he says. "I don't have a hometown team, I don't cheer for anyone — maybe Yale a little bit, but beyond that I couldn't literally care less who wins and who loses."
Lee grew up in New York City, as a self-described "goody two-shoes" who spent most of his time studying. He attended Yale undergrad, then enrolled in medical school there in 2016, planning to be a doctor.
Not long into medical school, though, a friend urged him to try sports betting, which was illegal at the time in all but a few states but widely popular nonetheless. He began with Ivy League basketball, wagering on games and posting insights on online message boards, and found that he enjoyed it.
"It sort of made intuitive sense to me how it was just another puzzle to solve," he said. "The market gives you a 'price,' it tells you a team is favored by two or three points, and then you say, 'No, I think that's wrong.'"
Soon, Lee found himself wading deeper and deeper into the betting world, learning from people he met online and eventually hiring others to help him. He sought advantages in unlikely places, learning more about Asian baseball than he'd ever intended to know after finding odds on those games that he liked.
As most fans watch big games between highly ranked teams, Lee prefers under-the-radar match-ups where he can find an edge. In late 2020, for example, before sports betting was legal in Connecticut, he won thousands on a college football bowl match-up between Houston and Hawaii after the Houston team was slammed by a COVID-19 outbreak. (He didn't actually watch that game, of course, because, in his words, "Why would I?")
Lee won't say exactly how much money he has made from sports betting, only that he reliably comes out ahead. At one point he left school to focus on gambling, though he returned before too long.
While Lee cites profit as his chief motivation, he says self-gratification drives him as well. Whereas medical school was all about the pursuit of knowledge, sports betting came with a satisfying finality. You bet on what was going to happen, and a few hours later you were proven either right or wrong.
This, Lee said, appealed to his personality type. Brian Patt, a friend who met Lee online and talks sports with him frequently, describes Lee as "high energy." Lee himself puts it differently.
"I am kind of a New York City [a-hole]," he says. "I get very satisfied when I'm right."
When sports betting became legal in Connecticut last year, Lee happily began placing wagers at sanctioned locations. Though he'd sometimes drive to the casino to place large bets, it was easier to do so at an off-track betting site near where he lived in New Haven, operated by the lottery and its affiliated sportsbook, PlaySugarHouse. Before long, he was on a first-name basis with staff there.
Then, with little warning, came the letter.
"Effective immediately you are Ejected from all PlaySugarHouse Sportsbook retail locations," it informed Lee. "You are also prohibited from entering the premises of any PlaySugarHouse Sportsbook facility in the State of Connecticut."
According to the letter, Lee had committed three offenses, allegedly captured on video: He was placing bets "just below kiosk limits," he was utilizing multiple machines at once, and he was placing bets on behalf of other people.
Lee denies placing bets on behalf of other people. He admits betting large quantities using multiple machines ("I am really damn good at manipulating the kiosks") but says no one had ever told him that wasn't allowed. In fact, he has been unable to find any documentation of these rules he is said to have violated. The kiosks are self-service and while there is video surveillance, nobody watches over a user's shoulder.
"In my view, there's a big miscommunication from ... the CT Lottery to the good guys at Winners and Sportech who are actually trying to run the business on the ground," Lee said.
In an interview, Greg Smith, the CT Lottery's president and CEO, declined to comment on the specifics of Lee's case, except to emphasize that Lee is banned only from retail locations, not from betting online.
Speaking generally, Smith noted that Connecticut's state statute grants gaming operators such as the CT Lottery the power to designate "prohibited patrons" in instances when a bettor breaks the law, places bets on behalf of others, or is determined "to pose a threat to the integrity of gaming due to cheating or involvement in criminal activity." He said officials tend to take note of bettors who aren't behaving "normally."
"Normal betting looks like this: Somebody walks up to a kiosk, puts their money in, places their wager, walks away with their bet slip," Smith said. "It's when people aren't acting normally that things come to our attention to either look more closely, engage with the person or monitor their activity."
Because failing to act "normally" didn't seem to Lee like a reason for him to lose his ability to bet, he hired an attorney and told the lottery he wanted to appeal his ban. Months went by until finally, in early December, he appeared for a hearing in front of Smith and other officials, arguing that he hadn't intended to break any rules and that a lifetime ban was excessive and unnecessary.
As of early this week, lottery officials had not informed Lee whether his ejection would be upheld or overturned, but Lee is confident he'll be banned for good. Smith and other officials, as Lee recounts it, told him that they had broad authority to operate sports betting as they wished and that they were within their rights to bar him from retail locations.
The most significant evidence the lottery presented against him, Lee said, was a video that supposedly showed him betting on behalf of a man at the kiosk next to him. In reality, Lee insists, he was actually placing a bet for himself, as the man watched.
Prior to the hearing, Lee had told CT Insider that he no longer wanted to move ahead being interviewed and would instead let the process play out quietly. His experience in front of the lottery executives changed his mind.
"The lottery seems to be willing to use no evidence to back up to their claims as to what I am doing," he said. "It further emphasizes the point that they don't know what they're doing."
To lottery officials, Lee's story seems to be about a bettor who flew too close to sun, who attempted to exploit the system and got himself in trouble.
To Lee, it's about a quasi-public state agency abusing its power to keep from losing money. He contrasts the lottery with the tribal casinos, which publish their rules publicly and, as he sees it, better understand the cat-and-mouse game between bettors and operators.