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Alex Stein loves watching football, playing football and betting on football. That last activity has emerged as his favorite over the years, and at times it has been a lucrative pastime. He just has one problem: The Dallas Cowboys.

“It kills my fantasy team, because I always draft the Cowboys,” Stein said. “I can’t bet on other players in the NFC East because I hate those guys.”

Stein, 27, said he’s lost a lot of money because of his emotional investment in the Cowboys.

“I’m down maybe 70 or 80K,” he said. He’s not sure exactly how much, but he’s at a net loss over his years of betting. Still, he loves it. He really, really loves it. His voice is full of excitement and happiness, even when he talks about losing thousands of dollars, because he’s still talking about football. Little else seems to matter.

He’s in five fantasy football leagues (for the uninitiated, that means he has five rosters made up of players around the league, whose performances earn him points against his opponent’s roster), and he also bets on the head-to-head matches.

It may seem crazy how someone could lose so much money over fantasy matchups, but betting on football adds up. Some of Stein’s leagues require a $1,000 buy-in, and he bets on college football as well. He says his alma mater, LSU, usually makes up for a lot of the money he loses on the Cowboys.

Alex Fantasy Football

Alex Stein

Stein said he doesn’t have debt, but he also doesn’t keep detailed track of his finances. His work in reality TV (behind and in front of the camera), as well as his work as a bail bondsman and car salesman allows him a comfortable lifestyle, to say the least.

“I can’t watch a game without putting money on it. It’s boring,” Stein said. “It’s an addiction, honestly, but I don’t think it’s ruined my life.”

Stein is definitely on the extreme side, but he’s not alone when it comes tying finances with football.

Sloane T. Davis is a self-described sports junkie in Los Angeles who teams up with a friend for fantasy football strategy. They had played in leagues separately but wanted to join an expensive league a few years ago ($1,000 buy-in), so they pooled their resources.

They’ve been partners for about 5 years, and they’re currently in two leagues (the other league cost $500 to play, and in both leagues, they split buy-ins and winnings).

“We are the reigning champions 3 years in a row,” Davis said of their performance in one league. The other: “Last year we came in second because Matt Forte couldn’t reach a 1-yard hashmark.” It was a huge let-down (a couple hundred dollars’ worth). Such is the life of sports fans.

Still, her winnings allow her to live the sports-fan life she loves. Not only does she set aside money for the next season of fantasy football, she also uses the rest to watch her favorite teams, the New York Jets and San Francisco Giants. If games are west of the Rocky Mountains, Davis goes.

Those rewards don’t come without work. She and her partner have daily conference calls and discuss roster choices for hours a day, but it makes her happy, and it has paid off. Overall, Davis has won about $10,000 playing fantasy football.

Not everyone is as intense as Stein and Davis. Kurt Johnson, who owns a fitness business in Los Angeles, has been in the same fantasy football league with friends for 10 years, and he likes how it brings them together every year, even though they live across the country. It costs $100, and having money on the line keeps everyone engaged.

“It’s fun to have that component to it,” he said, noting that it comes down to less than $10 a week for the season. “Fortunately, I’m in a point in my life that $100 for a fantasy football season isn’t a big deal.”

Fantasy football even helped him pay off debt. When he graduated from college, he had some credit card debt, and he joined a big league at work. It cost $200, and a partner at the firm doubled the pot, so when he won, he ended up with $4,000. He used it to pay his debt.

Considering the impact credit card debt can have on your credit scores, that’s a pretty smart way to use your winnings. The amount of debt you have is one of the biggest credit score factors. You can see how your debt is affecting your credit score for free on Credit.com.

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Main image: iStock; Inset image courtesy of Alex Stein

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