Daniel Chiang placed his first sports bet a few years ago.
“I remember [it] was something super random,” he told Deadspin. “It was an under, two goals on a World Cup game if I remember correctly. And I think it was like Denmark versus Finland or something? I knew nothing about either team.”
But since that bet, Chiang became obsessed with sports gambling and analytics. A few years after placing his first bet, Chiang left a career in finance to become a sports gambling expert and CEO of Line Sniper, a sports betting service that aims to better inform the casual gambler.
Early this year, Chiang put $30,000 on the Tampa Bay Rays to win the American League pennant and reach the World Series.
[Updated October 15, 2020, 10:15 pm] He stands to win $300,000.
“Everything in sports betting is similar to the equity markets,” the Wharton grad told me. “You’re always willing to buy teams or commodities if the price is right.” And the Rays future bet, according to Chiang, was right.
“We like teams that are undervalued by the market and the Rays are traditionally one of those teams,” he said. Chiang also put future bets on the Padres, Marlins and Cleveland to make the World Series. Those bets won’t cash out, obviously. But a Rays win will pay for Chiang’s other bets and then some.
Chiang says he simulated the Rays seasons “thousands and thousands” of times before he placed the January bet. After the analysis, he liked his chances. “From a full data side, it really lined up to a lot of things we were seeing,” he said.
“They had a lot of undervalued bullpen arms. They had one of the best rotations in the league.” And Chiang thought Tampa, not exactly the preseason favorites in the AL East, would be able to get into the playoffs like they did in 2019.
He “saw that they were gonna make the playoffs and then just saw how they would stack up in a series and projected out the betting lines for each price.” The price he got on this bet was “significantly better than what we were projecting out at the top.” In other words, he saw better value in the Rays than he did with the favored Dodgers and Yankees, who were knocked out of the postseason by Tampa last Friday.
But Chiang has not won his money yet. There is still time left in the series and no 3-1 lead is safe in sports. [*Now 3-2 lead]
Updated again! October 17, 2020 at 9:00 a.m. [**Now 3-3 tie!]
“I would say there’s always a little bit of nerves or a little bit of stress that everything [could] fall apart,” he tells me. “This series could easily have been three one the other way if Altuve makes two easy throws to second and first base.”
The ball can bounce thousands of different ways. Sill Chiang feels confident enough in his method that he knows it will literally pay off.
“You have to believe in the kind of the process you created,” the Line Sniper founder says. “Ultimately, if you’re making good bets and you’re making bets that mathematically make sense that over the long run, you’re going to make money.”
Chiang plans to watch today’s game in solitude with his computer at the ready to check batting averages, bullpen rotations and other baseball statistics completely out of his control.
“It’s going to make no difference on the game,” he admits. But he’ll do what he can in hopes of one more Rays win.
“I’m crossing my fingers,” he says. “If not tonight, I’ll take tomorrow as well — as long as it’s one of these three next games.”