Fantasy Football Gets Real With Insurance, Lawyers

When you manage a league in the fantasy sports world, you might consider hiring a lawyer, or buying some insurance in the real world.

While pen-and-paper fantasy sports became popular among fans in the early ‘80s, ESPN introduced the first Internet fantasy baseball game in 1995. Today, the fantasy sports industry is worth approximately $1.2 billion, according to market research firm IBISWorld, as more than 270 businesses make money off the “dream teams” managed by Average Joe sports fanatics. And it’s not all fun and games when it comes to fantasy companies, as insurance brokers and lawyers – and even trophy makers -- are finding a spot in the market. “We came up with the idea when Tom Brady got injured in 2008,” says Henry Olszewsky, a vice-president of Intermarket Insurance who runs For players who drafted Brady high that year – and made sizeable investments to enter the league – their chances of winning became pretty much zero. “I looked at a similar kind of policy that professional franchises use to ensure their players, so if you have a Tom Brady, you pay him $100 million, and $40 million is guaranteed. If he breaks his leg, he’s still guaranteed that money, so the franchise takes out policies against catastrophic injury,” says Olszewsky. For a fee of 10% of the costs of entering a league, insures a roster’s top player(s). Injured players or those with a high risk of getting injured aren’t available for insurance. Last year, Olszewsky estimates his company insured 2,000 policies for fantasy sports investments, with the majority of policies covering investments between $300 and $500. If insured players get injured and miss nine or more games, policyholders are paid the full sum of their investment. And while Olszewsky says is just “holding on for now” when it comes to profits, he’s not the only one who sees dollar signs in fantasy insurance. This year, Aran Insurance co-owner is launching Fantasy Player Protect, which offers insurance for a fairly flat fee between $12 and $18 a player. “Each player is priced separately, and the insurance policy is on the number of players you insure,” says Tim Kenny, a co-owner of Aran Insurance. Like, Fantasy Player Protect will pay out sums to policyholders whose insured players miss nine or more games. Since launch in mid-August, Kenny says their site has received more than 50,000 hits, with several thousands of people registering as users.By-the-Books Approach to Fantasy Disputes And where there’s a need for insurance, there’s also room for lawyers. Enter “I began resolving fantasy disputes for friends around the beginning of 2001 while I was in law school,” says Baruch University law professor Marc Edelman, an attorney who practiced at Skadden Arps. As word of mouth about his fantasy sports legal expertise spread, Edelman decided to launch a website to accept disputes, which range from arguments about fantasy leagues’ constitutions to spats about trades. “I would say that on a good year, I settle between 50 and 100 disputes,” says Edelman, who charges $15 for a single dispute. “I’m a professor, so it’s not intended to make a substantial amount of money.” To weigh in on a fantasy-sports dispute, Edelman views the league’s constitution as a contract. But when there’s not enough detail to decide based on the constitution alone, he says he turns to fantasy-sports precedent, looking back at the decisions he’s made over the years. “I wanted to come up with case law precedent for resolving disputes in fantasy sports … As a professor, I do a wide range of consulting, including in the fantasy sports world,” says Edelman. There’s a Trophy for That Just like real sporting tournaments, many fantasy leagues are now awarding winners impressive trophies for their accomplishments. Dave Mitri, a fantasy sports fan himself who started playing fantasy football in 1990, says he made his first trophy as a joke for his fantasy-league friends. “I was going to art school, and I thought it would be funny to sculpt the trophy. I also won it the first year, and wanted to rub it in,” says Mitri, who runs “It was a really large guy sitting in a recliner, and my friends went crazy for it,” says Mitri. “Once the Internet came about, I thought I should maybe sell these things online.” The trophies cost as much as $399, with the cheapest models selling for $79. Mitri makes them in Brooklyn, where he sculpts the 12-inch souvenirs out of resin and hand-paints the figures for a bronzed finish. One of the most popular figures, he says, looks like the Heisman trophy, but instead of the football, the player is holding a six-pack and a remote. “It speaks to what guys do when they’re watching football,” says Mitri. Tom Harkins, who runs, says perennial trophies are extremely popular at his site, which made more than $100,000 in revenue last year. “They love the history of the league, and with a perennial trophy … it records the champions every year,” says Harkins. He says he built more than 1,300 trophies last year, which range from $5 to $500. “The best decision I ever made was to launch this site,” says Harkins.