Betting on an NFL Sunday

The multi-story, adobe-style house is located 30 minutes off the Strip in Henderson, Nevada. Sitting on a corner lot in a gated community littered with palm trees, it's nice, but not overly extravagant.

You certainly wouldn't guess that crammed into an upstairs office inside is the three-man brain trust of a successful, high-volume sports betting syndicate.

There's a former Chicago financial trader, a former high school basketball coach from Illinois and a poker pro who doesn't even watch the games. They're regular, easy-going guys in their 30s, who make a living gambling. And they're preparing for the busiest 30 minutes of their NFL Sunday.

It's an open, informal setting, with two desks, a couch and four TVs tuned into the early slate of NFL games and the final day of the Presidents Cup. There's an oversized cutout of Tiger Woods on the wall, along with St. Louis Cardinals and Boston Celtics memorabilia. It's not really a man cave, though, not a place to chill out, drink beer and watch football with buddies. The only food out is a bucket of ice with some Red Bulls and a box of donuts. This is very much a high-stakes grind.

When I arrive on this Sunday morning, the syndicate, incorporated as Imawhale LLC, has action on everything, except the Tennessee Titans. All morning, they had tried to bet on the underdog Titans against the Houston Texans through mobile apps offered by sports books in Las Vegas.

"Every bet was rejected," says Jason Garrett (no, not that Jason Garrett) with a frustrated, yet resigned tone. "It's a good thing; they're down 24-7."

Some books will take the syndicate's action; others won't. No one in the room is really happy about it, but they all seem to understand that being limited or cut off completely is part of the bettor-vs.-bookmaker battle that decides their salary.

"We provide liquidity on the side that the public doesn't want to take," Shane Sigsbee, co-founder of Imawhale Sports, says of the books that do take their action. "So they don't view us as pariahs. They view us as liquidity providers."

Garrett and Dan Thomson, both tall, slender and wearing shorts and golf shirts, are the top traders for the syndicate. Garrett was just 27 when he left his job as a high school basketball coach in Illinois in 2013, packed up his red Mustang and moved to Las Vegas to play poker, before joining the syndicate. He's the definition of a professional gambler: a sports bettor, poker player and admitted card counter, who's listed in the vaunted Griffin Book. Advantage players know what that is: a database that they don't want their name in.

Thomson is entering his third year with the syndicate. He was playing poker out of Rochester, New York, when he decided to bolt to Las Vegas to join the syndicate. Besides his beloved Buffalo Bills, he admits that his sports knowledge is basic and that when he works from home, he doesn't even have a TV in the room. He can, however, tell you exactly how much a 1/2 point is worth on a WNBA first-half over/under.

"I'm more interested in working out formulas in Excel," Thomson says with a smile. That's the life of a true professional sports bettor."

Sigsbee is on the couch in a pink, button-up shirt, slacks and baseball hat. A Notre Dame alumnus with financial background, he started Imawhale Sports in 2012 as a side project to go along with his poker-staking business. He currently stakes 75 poker players in cash games. The poker side of his corporation is more profitable than sports betting for now, but the gap is narrowing, he says.

Garrett, Thomson and Sigsbee each bet individually and share varying percentages from the syndicate's profits. It's a 70-plus-hour-a-week job during football season and can be an absolute grind.

"We're not handicappers; we're line-shoppers," Sigsbee explains.

They do their shopping online, closely watching a few select offshore sportsbooks known to cater to sharp bettors. They know other groups are doing the same thing around town, which makes the window of opportunity to grab a preferred line just seconds-long.

"When certain offshore books that you know are sharp and move their lines first, there are books in Nevada that lag behind," Sigsbee explains. "But the secret sauce is quantifying how large the move is and is that move great enough to overcome the vig you're paying to make the bet. What we do better than anyone is we quantify the moves from a mathematical standpoint, of every derivative, of every single sport. We can tell you how much a ½-point is worth on an NFL total when it moves off of 45 to 45 and a half."

They've done it long enough that they can calculate the value on the fly, but in addition to the quick-thinking math, the syndicate's success also relies heavily on effort.

Garrett and Thomson remain focused on their monitors, staring at updating odds screen that show the point spreads at 10 or so sportsbooks, offshore and in Las Vegas. The screen lights up when a line moves, and, when the line moves at a respected book, the syndicate places a wager.

"A lot of it is just, 'Do you want to work harder than the guy sitting in front of his computer at the casino?'" Garrett says.

"It's a tough gig," Thomson adds.

"It would be easier," Garrett says, "if we all had jobs and this was just to make a little extra money on the side and we were betting $500 units, but trying to make a living, we've got to bet bigger."

Imawhale Sports is in its fifth year and growing. The first two Saturdays of this college football season were among the syndicate's best ever. They placed 100s of bets on those Saturdays and got more than $500,000 in play each day.

"Back when we started, we maybe did $2 million in volume in a year," Sigsbee says. "Now, we do $2 million in a couple weeks."

Except for the occasional baseball and preseason hockey bet, things are relatively uneventful as the first set on NFL games heads into the second quarter. As the games near halftime, the conversation dwindles. They've already bet $82,000 on the day, but in the next 30 minutes -- roughly 11:30 a.m. to noon PT -- the syndicate hopes to place nearly one third of the $250,000 it plans to wager Sunday. Halftime lines are a big opportunity.

"There's so much action coming into these books, both domestic and offshore and everywhere else [during halftimes]," Thomson says. "An NFL game line that's posted Monday or Sunday night for the next week has so much time to stabilize. Whereas these halftime markets, it's totally an unforeseen thing -- they open the doors and it's just a floodgate. Those lines fluctuate quite a bit, and anytime there's this rapid movement in markets, that's our opportunity."

During the halftime rush, each member of the team is responsible for certain types of wagers. Garrett is in charge of second-half sides. Thomson focuses on second-half over/unders. Sigsbee takes over baseball and preseason hockey.

These aren't enormous bets, but there are a lot of them. They call out the bet they're looking for and at what sportsbook:

• $600 on the under in the second half of the Cincinnati Bengals-Cleveland Browns at a Boyd Gaming book.
• $575 on the Carolina Panthers +6.5 in the second half versus the New England Patriots at CG Technology.
• $550 on under 24 Titans-Texans in the second half at the Wynn.
• $2,200 the Buffalo Bills +3.5 in the second half versus the Atlanta Falcons at CG Technology.

"How we doing?" asks Sigsbee.

"Down $4K," Garrett answers.

"It's funny," Thomson interjects, "these guys like sweating results. I very much do not look. I'd just rather grade it all at the end of the day. Guess it's the poker mindset ingrained in me: Get the money in good and don't worry about the results. In the long run, you'll win."

Garrett responds, "If I didn't sweat the games, this would be the most boring job I've ever had."

During the flurry of halftime action, Thomson's phone glitches, preventing him from logging in to his Wynn race and sports app. He debates whether rebooting his phone will cost him more money from missed opportunities than it's worth trying to get the Wynn's app up and running. He elects to not to restart and resorts to his other apps.

Sigsbee zings Garrett about the room temperature. "I didn't think that AC unit was ever going to come back on," Sigsbee jokes. "I didn't know if we were trying to save money after a rough day yesterday."

More bets come rapidly, including a $550 wager on the New York Jets +3 in the second half against Jacksonville, along with New York Islanders preseason action.

Sarcastic cheers are released when Sigsbee's $1,495 bet on under 24 in the second half of the Titans-Texans game is accepted by CG Technology. Garrett updates the running tally, telling everyone they are down more than $7,000.

College football Saturdays, when there are often 50-plus games, are much busier for the syndicate than an NFL Sunday. This week, they were down as much as $37,000 heading into the last college football kickoffs of the day and ended up down only $13,000. "It was a great comeback," Sigsbee says.

When all the second halves of the NFL games kick off, the syndicate has wagered roughly $40,000 during the 30-minute flurry. With the early London game, there was one less opportunity to make halftime wagers on the late slate.

"That's a little light," Thomson says.

Light, but profitable. By the time the first set of games end, the syndicate's fortunes have flipped, from $7,000 down to up $10,000, a solid half day of work.

This Sunday has been smoothest of the first month of the NFL season. Their odds-feed service has been dealing with recent DDOS attacks that leave the syndicate blind to the market. It's a hassle, but also an opportunity.

"The whole grid goes off," Sigsbee says. "But, here's the thing, the sportsbook managers are looking at exactly what we are. If nobody has any market to look at, it creates a pretty interesting situation. It's been happening a lot the last couple weeks."

"When we're blind," adds Thomson, "the books are blind, too. As much as it's tough for us, it also creates some opportunities."

"Big opportunities, too," says Sigsbee. "Things can really get out of whack."\

The syndicate's future, while promising, is also hazy. Legal sports betting is expected to expand outside of Nevada in the coming years and its impact on the syndicate is up in the air.

"I kind of like the current status," Garrett says. "Nevada's the only state that it's legal; I think that kind of benefits us. As long as there are people making $25K sitting behind a computer pushing buttons, we're going to be able to out-think and out-work them. I think there is some risk if it becomes legal nationwide, the whole landscape is going to change enough that we might not like the end results."

For now, the results are good, but it's certainly not the glamorous lifestyle often associated with being a professional gambler.

"When people think they want to be a professional gambler, they don't realize that this is what they're signing up for," Thomson says. "They think there's going to glitz and glory, and they're going to be some casino high-roller. In reality, this is what it looks like.

"When I meet someone, a professional poker player or sports bettor, and I ask them if they'd recommend it to someone, the guys who say, 'No. Absolutely not,' I think, 'OK, you probably win.'" http://www.espn.com/espn/print?id=20913399&type=Story&imagesPrint=off