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Finding Fortune in Fantasy Football

Football fans turn their fictitious hobby into real money
Michael Kaplan
From the Print Edition:
Jim Belushi, November/December 2010

Last December 27th, as the NFL season neared its completion, the Dallas Cowboys confronted the Washington Redskins. It was a big match-up for Dallas. Winning this game would clinch a playoff spot. It was also a major four quarters for Jason Conn and nine of his friends and relatives. Far from the Skins' FedEx Field, Conn and his guys watched the action from inside a finished basement in Ohio. But they didn't really care whether or not Dallas made it to the play-offs. On some level, they didn't even care about the game. Still, the guys had $300,000 riding on quarterback Tony Romo putting in a stellar performance.

Conn and his investors bet serious money, but rather than banking on a team winning, the group of friends place their bucks on individual players and create their own teams. They partake in a scaled-up form of fantasy football-in which you put together a theoretical team, compete against other theoretical teams, and get points by having players who gain yardage via passing or running-with six-figure sums hanging in the balance.

"Before the Dallas game began, we trailed by 12 points," says Conn, referring to fantasy points. "But we still had two guys in the running and the other fantasy team was done. Nevertheless, I have to say that it got very quiet inside the rec room."

Then the game began and Dallas quarterback Tony Romo-one of Conn's key players-flitted in a four-yard touchdown pass. Jell-O shots in the Dallas Cowboys colors were passed around and quickly consumed. The $300,000 first-place prize loomed and, in short order, Team Conn accrued the points to seal their win. Bottles of champagne were promptly popped; Cohiba cigars got clipped and lit; a long night of celebrating ensued. "It went beyond the money," says Conn. "There were 10 of us, and the $300,000 was split evenly. It came to $30,000 per person. But it's great to know that we went up against the best fantasy football guys and beat them. We reached the pinnacle of fantasy football."

Fantasy Football is a huge U.S. pastime, and its 22 million annual participants are finding out how hard it is to put together a winning lineup every Sunday. But Conn ranks among an elite group. Guys in his circle risk as much as $25,000 per team with the hopes of finishing first and taking home enough money to finance the off-season.

Dustin Ashby co-owns World Championship of Fantasy Football, a primary facilitator of the big-money leagues. He takes an innocent obsession and turns it into a high-flying event that he likens to the World Series of Poker. But Ashby has competitors: Fantasy Football Players Championship allows for exceptionally flexible lineups. Another fantasy organization, National Fantasy Football Championship, holds live drafts in eight cities across the United States. runs fantasy football competitions that resolve in a single day (as opposed to a season), and you can multi-team, buying in as often as you like over the course of a single game day. Operating in a less commercially driven but no less competitive
environment, a dozen or so high-stakes poker players take fantasy football to the next level by putting together their own league. It can be as cutthroat as a high-stakes hold'em game in Bobby's Room at the Bellagio.

The poker league's buy-in is $5,000. But that entry fee pales next to the side action. FullTilt pro Erick Lindgren has been known to wager as much as $500,000 in ancillary propositions. He and fellow poker stud Daniel Negreanu once had an ongoing weekly bet in which they each pitted one of their players, heads up, against the performance of the other guy's player. "My biggest bet was for $25,000 against Erick," says World Series of Poker bracelet-winner Gavin Smith. "It was a must-win for league [meaning that if neither guy's team finishes first for the season, no money changes hands] and Erick wound up winning. That year didn't work very well for me. My team came in third or fourth, but it wasn't enough."
Even poker stars with shallower pockets get in on the action. Nick Rainey, who's become a runaway success on the online tournament circuit, has been competing in the poker players' fantasy football league for the last three years. "I'll maintain four or five side-bets in which my team goes up against the teams of other guys," says Rainey, acknowledging that he used to think fantasy football was irredeemably goofy. "Now that I'm doing it, though, I find it really interesting. It creates a whole new way of watching a day's worth of football games."

Fantasy football grew out of old-school rotisserie league baseball, beloved by stat junkies who enjoyed placing valuations on minutiae of the game. Initially, this sports-betting derivative was indulged in by friends and coworkers. Then, as the Internet blew up, so did the spread and breadth of fantasy sports. While basketball and hockey leagues are up and coming, football has proven to be an especially popular iteration, largely because the game's schedule is more controlled. That makes it more manageable for people who have things in their lives that go beyond theoretical teams. "It definitely gets a bit excessive," acknowledges champion Jason Conn, who's first draft for this season kicked off in late August. "I purposely gave my share of the $300,000 in winnings to my wife." Is this payback for all the time he devotes to fantasy football? Conn quickly adds, "I figure that it will give me carte blanch to go Las Vegas for the fantasy football drafts."

When it comes to fantasy football, regardless of the level at which you engage, the draft is of utmost importance. The more sophisticated leagues apply an auction approach. With this method, each team receives a certain amount of draft dollars (say, $1,000) and they can spend that much on bidding for players who will comprise a team. For the savviest team owners, this element of the process presents one more opportunity to find an edge. "Let's say I have no interest in owning Drew Brees," says Gavin Smith. "Maybe I'll bid him up a little bit anyway and hope that somebody jumps in and gets Brees for more than what he wanted to pay. Sometimes, though, you get stuck with a player you can't use. But, often enough, it leaves opponents with less money in the later stages."

This is particularly useful for Smith, as he explains, "My player-buying strategy is to wait until later in the draft. Then I get more marginal players for less money. The top three or four running backs always go for inflated prices. Same with the top quarterbacks. I let other people grab those guys and I wind up with a more balanced team at the end."

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