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'Emotional roller coaster' ride ends & Rays bettor wins $300K on AL pennant [UPDATED]

Tampa Bay is going to the World Series.
Tampa Bay is going to the World Series.
Image: (Getty Images)

This story has been updated

Gamblin’ man Daniel Chiang made a bet in January that put him in a position to win $300,000 on a $30,000 wager if the Tampa Bay Rays got to the World Series. After taking a 3-0 lead in the ALCS against everyone’s favorite nemesis, the Houston Astros, it looked like money in the bank, but the ’Stros actually came back to tie it and send it to Game 7.Chiang sent us an email after the game:

“Never a doubt, kidding. This game in many ways encapsulated the emotional rollercoaster that this series has been for me. When they pulled Morton after throwing a fantastic game that was definitely a nerve racking and a very Tampa Bay Rays decision.

I can definitely say I’m relieved that the series is over and that the Rays were able to pull it out. I think the most difficult things to do that I’ve learned in sports betting and trading is sticking to your guns when it feels like things are turning against you. Often times it doesn’t work out but ultimately it put me in the best position to succeed and luckily on this occasion it worked out!”


On Thursday, we spoke to Chiang about why he picked the Rays to win the AL pennant, long before the shortened 2020 Major League Baseball season.

Chiang was confident in his bet but, in the back of his mind, he knew there was still time for the wheels to come off.


No series lead is safe, as Chiang and every sports bettor knows.

“I would say there’s always a little bit of nerves or a little bit of stress that everything could fall apart,” he said on Thursday.

That was just 48 hours removed from the lifetime it probably seemed to him as he actually watched the wheels come off.

Today, the series is tied 3-3, and heading into a decisive seventh game tonight. We caught up with Chiang again to see how much he’s sweating.


“As you can imagine sitting up 3-0 in the series I felt pretty good about [it, but] as the games have ticked by, the nerves have certainly ticked up,” Chiang told Deadspin via email.

Chiang had options to hedge his bet throughout the series, but he’s refused to play it safe. “So far the single most frequent question that I’ve been asked by people is: you surely hedged earlier in the series when the Rays were up 3-0, 3-1 and potentially even 3-2? The quick and direct answer to that question has been a resounding NO.” Chiang has not hedged a single dollar in the series. He still trusts his instincts and analytics from January.


“I always try to have the math, data and analytics guide our decision making to the best of our abilities with the knowledge that ultimately good analytical decisions is the path to long-term success,” he writes. “Hindsight in sports betting is always 20/20 and saying that you had a crystal ball that ‘knew’ the Astros would come back in the fashion they did would be disingenuous.”

For someone who could win (or lose) thousands of dollars tonight, Chiang sounds relatively calm, if not … excited? That’s betting baseball, Suzyn.


Also for the first time ever he’ll be live tweeting his thoughts and his in game thoughts and analysis @linesniperhq.

“Heading in to tonight, I plan to have maintain the same routine as usual, watching the game in solitude,” as if that will help the Rays. “Fingers crossed for tonight and hopefully those Tampa Bay Rays bats heat up.”

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