I Tried to Get Rich Playing Fantasy Football

I don't care much for sports or gambling, possibly because all that was ever on in my house growing up was football or World Poker Tour, and no one wants to like what their parents think is cool. My father is the kind of man who always tries to start never-ending Texas Hold 'Em games at Christmas and will tear up contemplating the accomplishments of great thoroughbred racehorses like Zenyatta (whose racing record I can now recite from memory). In my extended family, celebrations like wedding anniversaries are normally celebrated at a dog track in Rhode Island.

If my clan's traditions seem odd to you, walk into any bar with a TV this fall and witness the crowds of bros of all ages and genders moaning, cheering, and praying over yet another football season. Some of them are powered by hometown pride or pure love of sport, but it's no secret that nothing spices up the experience of watching three hours of large men falling down like gambling. And these days, gambling often means daily fantasy sports (DFS).

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If you've never heard of DraftKings or FanDuel, congratulations, you don't own a TV. The two DFS sites offer people the chance to draft real players onto an imaginary team, watch as the players compile stats like the number-generating machines they are, and then win or lose money based on their performances. The hook is that unlike regular fantasy sports, DFS games are won or lost in the course of a single day, making them the crack cocaine to regular fantasy's marijuana. (The sites make money by taking a percentage of everyone's entry fee.) Like all gambling-based ventures, DK and FD highlight the people who have won thousands of dollars playing these games, the idea being to make it seem as if sitting around, drinking Bud Light, and fiddling around with your phone on the Lord's day might be more financially beneficial than going out and doing errands.

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We're in a DFS boom not too dissimilar to the online poker boom of the 2000s. The difference is that the authorities have been quicker to crack down on potentially shady practices. Last month, a DraftKings employee won $350,000 on FanDuel, prompting an investigation by the New York State Attorney General's office and a class action lawsuit over insider trading. Additionally, the FBI has launched a probe into both DK and FD.

Controversy aside, as someone who has involuntarily absorbed a basic knowledge of both sports and betting through osmosis and who also likes eating nachos more than cleaning, I figured it might make sense to see if I could win at fantasy sports and be like the people in the commercials who claimed their lives were changed by a few taps on the app. Plus, I'm still looking for anything I can invest in that will eventually yield a Playstation 4.

As one commercial for FanDuel promised, I could make money if I was "smarter than the average fan," and have you met an average sports fan lately? I figured it wouldn't be too tough.

I was very, very wrong.

To play DFS successfully, you have to have a working knowledge of all 32 NFL teams, each with more than 25 starting players apiece, making for a ridiculous amount of data to manage.

"It's eminently possible for a novice competitor to win big money on DraftKings or FanDuel—if the contest were limited to two or three NFL games," Jay Clemons, a fantasy guru who has written for Sports Illustrated and FOX Sports, told me. "But it's rather difficult to pull off the feat, when accounting for a full or near-full slate of NFL outings on a typical Sunday."

Clemons likened the whole experience of playing fantasy to a "crapshoot," and conceded that predicting NFL games on a week-to-week basis is pretty much impossible for mere mortals.

"Otherwise, the so-called fantasy experts at various Web sites would be spending all their time in Las Vegas—capitalizing on that knowledge—with no desire to share their findings with a free audience," he explained.

That doesn't mean there isn't an insatiable appetite out there for articles breaking down fantasy sports. (Clemons himself writes 17 stories per week during the NFL season.) When I headed to RotoGrinders.com, a site which boasts, "If we can't help you build better lineups, no one can!" it felt like my eyes were on fire. There was an almost-seizure-inducing amount of sportsball-related content, and I knew I had no hope of sorting signal from noise.

So, ultimately, I logged on to DraftKings, dropped in $50, and tried to "go with my gut," which meant just picking out players I'd already heard of. After a few minutes of this, though, I realized that I only knew football players who had been accused of domestic abuse or rape, which meant my team was basically the Mon-Stars from Space Jam and not a team with any potential to win. I then re-jiggered things a little bit by looking at sports book odds online and seeing which teams were expected to crush the competition and drafting players from those squads.

Eventually, a male coworker could not bear to see me do this, grabbed my computer, and fiddled around with my team until his eyes glossed over—all behavior I would have taken to suggest a serious gambling addiction had I not previously observed DFS bros in the wild. Anyway, for all of his passion, it turned out he was no wiser than I was. Had I not given over the reigns to my team and had kept my original QB, I would have ended up in third place rather than sixth and become $50 richer. That's like, 1/8 of a PS4, dude.

To be clear: I'm pretty sure this is how gambling addictions start.

In gambling parlance, I was a "fish" as opposed to a "shark." According to data from Sports Business Daily, in the 2015 baseball season, 91 percent of the profits on DFS sites went to just 1.3 percent of the players. That same tiny percentage of users also paid 40 percent of the entry fees.

You see, despite what the ads on TV tell you, the only people winning at this game are entering a ton of money into it, playing hundreds of contests at a pop, and are really fucking good.

Take for instance David Kaplen. He was super into fantasy sports 15 years ago—long before the DFS boom—and realized he was gifted at it. He started playing 15 to 20 season-long games every year, in every sport, and honing his skill alongside a restaurant job that he described as dead-end when I spoke to him on the phone.

Kaplen started fiddling with FanDuel when it came along and soon came to a crossroads. "I put it down on paper: 'What do I make every day that I go into the restaurant, and what can I make every day on average playing this game right here,'" he told me. "The numbers were a lot closer than I would have thought, so I went, 'Let's give this a shot.'"

Today, he's a full-time DFS player. When two sports are in-season at the same time, Kaplen spends five to six hours a day studying stats. Every week, he builds 15 to 20 of the best NFL lineups he can, and enters all of them into whatever contests strike his fancy, which usually include the million-dollar tournament and ones with $300 buy-ins.

Because he plays so much, and studies so hard, he's able to make it work.

"I think a lot of people see the advertisements and they think that it's somewhat realistic to go in and win a million dollars for $20," he explained. "And it doesn't work like that. What that will end up doing is draining you financially."

He said that it's not about hitting a home run, and that it wasn't too far off when the CEO of DraftKings compared the game to playing the stock market.

"The guys putting the most money out there right now, if you listen to what they say in interviews, the return on their money is about 8 percent," he continued. "It's not like a get-rich-quick scheme, they put that money back in. And that's some nice steady growth right there."

DraftKings and FanDuel raked in $60 million the first week of September, according to Bloomberg Businessweek, but that figure is expected to taper off as the NFL season continues. After all, people like me are gonna realize (or remember) that they hate gambling—or aren't good at it—and stop. Others will hear about the scandals surrounding the sites and figure they're safer sticking to regular fantasy sports.

Undoubtedly, though, people will still sign up. And it's hard to wrap my head around why—surely they must know that they won't be able to beat the house and the pros in the long-term.

"I think it starts with with the fact that Americans love gambling in general, and gambling appeals to the possibility that anything can happen," Dr. Timothy Wong, the co-director of UCLA's Gambling Studies Program, told me. "But the thing with daily fantasy sports in particular is that they combine so many things that Americans not just love but are passionate about—sports, big jackpots, competition, digital technology, beating your friends, claiming you did really well at any activity versus others."

He went on to say that gambling tickles a part of our brains that responds to potential rewards and allows us to play into a fantasy—for lack of a better word—that we're special and can beat the odds.

I told him that I understood what he meant, because I was only a few points away from winning without putting in any effort, and that I was so close I might actually be gifted at guessing.

That's when Wong explained the near-miss phenomenon, something very familiar to gambling researchers. He said that the feeling of almost winning can release more pleasure chemicals than actually winning. "That's what draws a lot of people to come back, to say, 'Well I was so close, maybe if I just keep going I can get there,'" he said. "But gambling doesn't work like that."

Although listening to the pro Kaplen talk about quitting his job and playing fantasy full-time was just as intoxicating as the ads DraftKings and FanDuel use to entice players, I realized that my chances of becoming a pro fantasy player were just as much of a long-shot for me as becoming a pro athlete.

"If you're playing in a contest that includes an entire weekend of games, the chances of anyone nailing the so-called perfect lineup may be akin to winning the 'Daily 5' drawing of a state-run lottery," Clemons, the fantasy writer, said. "In other words, you're better off being lucky than good."

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