Cigar Aficionado

Finding Fortune in Fantasy Football

Football fans turn their fictitious hobby into real money

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."

Rainey concurs, explaining that it takes more than a single, high-priced superstar to succeed at fantasy football. "One good guy having a great day will not help you. Tom Brady will not win your fantasy football league," he says. "You need five or six solid guys and one great guy." A key strategy going in is to understand the fellow team-owners in your league. "They might be die-hards who will go for certain players under any circumstance. If a certain type of guy's favorite team is the Indianapolis Colts, he will get Peyton Manning no matter what." He won't win fantasy football, but, says Rainey, "He also won't be rooting against Peyton."
That said, there are times when two key players are enough, especially if they're purchased at the right price. Such was the dream scenario for Jason Conn. "What worked out nicely for us was that the draft happened on a Saturday, two days after the first game of the season, and Chris Johnson [a running back with the Tennessee Titans] didn't do well on Thursday,"
explains Conn. "Because he had a disappointing first game, we were able to get him cheap and we picked up Andre Johnson [a wide receiver with the Houston Texans] in an earlier stage of the draft. By the end of the season we had the No. 1 running back and the No. 1 wide receiver. We needed Chris in order to win, and we got him because other people overvalued the long-term meaning of his performance in just one game."

Before Dustin Ashby ran a big-time fantasy football league, he was a serious participant. While he no longer competes, he has been paying attention with the unbiased eye of an outsider. He's noticed at least one trend that should be exploited by all fantasy participants, regardless of how seriously they play the game: "The NFL has moved to a more prolific passing attack. I think that there were 11 quarterbacks throwing for over 4,000 yards last year. That puts a premium on receivers. The thought-leaders in our format understand that, and they recognize the importance of picking versatile players who catch the ball."

The other thing that Ashby emphasizes is recognizing players "who are likely to be targets." By this he means that a winning fantasy team needs more than star athletes. It needs players who will get many minutes on the field and a lot of opportunities to rush, catch and score. "Maybe a wide receiver didn't put up 1,000 yards, but he got a lot more opportunities last year than he did the year before. Well, then you can predict that he will get even more opportunities this season. Lee Evans, on the Buffalo Bills, is a good example of that. Who else will catch the ball for Buffalo?"

Shawn Childs, a winning fantasy player who competes in 25 fantasy leagues during baseball season and is running teams in 15 fantasy leagues this NFL season, finds his edge in selecting under-the-radar pros and, just as importantly, minimizing his risk. For starters, he does his research and keeps sentiment out of the process. "Jonathan Stewart, the running back from Carolina, went early in a lot of drafts, but I see him as a player who's coming in off of an injury and I think there's a good chance that someone else can replace him in the lineup," opines Childs who finished second in the 2008 World Championship of Fantasy Football's $25,000-buy-in league. "I see him as a player to avoid."

More than many of his competitors, Childs views fantasy football as a moneymaking enterprise. It's something that he enjoys, but it also needs to be profitable in order for him to continue doing it. He acknowledges that at the higher levels, winning comes down to exploiting tiny edges, having a bit of luck, and putting in the time. "Depending on your lifestyle, you may or may not be able to do it," he says. "Between baseball and football, I get busy on 40 Sundays per year. " He hesitates for a beat, then adds, "In life everybody needs an outlet. For me this is a distraction with money at stake."

On the night of September 9, after the conclusion of this season's first NFL opener with the Minnesota Vikings opposing the New Orleans Saints, Chad Schroeder launched into a frenzy of wheeling and dealing for a season's worth of players. He had a dozen drafts to conduct during the long weekend in Vegas and, over the course of this season, he is managing 130 different fantasy teams, trying to turn a profit on his investment of approximately $145,000.

Clearly, he is not your casual fantasy football fanatic. Schroeder is a professional sports bettor. He has seen value leak out of his chosen area of wagering and recently turned to high-stakes fantasy football. These days, he estimates, half of his income derives from the fantasy leagues, which, he points out, require more than their share of work. "I go through every team, every week. It takes 10 to 20 minutes per team, and I have over 100 teams," says Schroeder, who was one off from winning a $1 million fantasy football prize two years ago. "Then I'm looking for free agents and putting in appropriate bids on them. Those run on Friday; if you don't have a backup plan by Friday night, you're not going to have one for Sunday. And Sunday mornings get completely chaotic when I need to solidify my starting lineups."

In addition to the $145,000 he has riding on league play, Schroeder makes as many side bets as he can nail down. Generally, he believes that he has an overall edge and plays fantasy precisely because he can take advantage of people who view it as recreation. "At minimum, there are usually three or four people in a given league who don't know what they're doing," he says. "Even if the other seven or eight do know what they are doing, the dead money creates an edge. Plus I know that I will do a better job than other people at picking up free agents. I've spent a lot of time doing this and I have gotten a lot of experience. I've developed a better feel for players who have value."

That said, Schroeder and the wiseguys of fantasy football all acknowledge that it's anybody's game. Even the dead-money players can end up with lifelines. As with any competition between professionals and hometown champs-fantasy football, at its highest level, most definitely qualifies as that-some guys come for the challenge and an opportunity to see whether or not they really are much better than the office-mates and neighbors that they routinely trounce in their home leagues. Whether competing in an organized league or a high-stakes operation of their own devising, they get opportunities to swing for big bucks while making like pro team owners. And they actively participate in a game that they love. "Before fantasy football, I couldn't have told you the second wide receiver on Seattle," acknowledges Ashby. "But now I, and, surely most of the guys in the league can, and there's financial value in knowing that. Playing fantasy football gives you a reason to care."

Michael Kaplan is a Cigar Aficionado contributing editor.