Will Leitch is the editor of Deadspin, our sister sports site, and his book God Save The Fan is now available at bookstores everywhere. He makes a cameo appearance here discussing why rich techies should avoid the world of team ownership.
Recently, I traveled to Dallas to interview Dallas Mavericks owner Mark Cuban for GQ magazine. (Stupidly, I mentioned my day job, as editor of Valleywag sister site Deadspin, at the beginning of the interview. I once posted about Cuban getting a lap dance from a friend, in what I thought was a clearly joking manner. Cuban was not amused and spent most of the interview accusing Deadspin of being the Inside Edition of sports. So that was fun.)

At one point, I asked Cuban about his interest in buying the Chicago Cubs. I already knew what his answer would be; I'd recently spoken to baseball sources for a story for New York magazine that made it clear Cuban, no matter how many billions he had, would never be allowed into the grey-haired old-fashioned clique of baseball owners. The guy has no chance. But, if just to promote himself as a tilter toward windmills, he stayed strong.

Don't count me out yet. Don't count me out. All [baseball owners] have to do is call other NBA owners, and there are NBA owners who are part owners of Major League Baseball teams, who see me in the meetings. They know me beyond what the media write and how websites like Deadspin characterize me. They know that I contribute as a partner. I hope, along with the money, that that's the important thing.

Frankly, you and I have a better chance of owning the Chicago Cubs than Mark Cuban does, and Cuban knows this. The only reason he's enjoying his time as owner of the Mavericks is because, ultimately, he wore down the rest of the owners to the point that they agreed with him. (It helps that he was pretty much right about everything he was initially criticized for.) But the NBA is the least old-school chummy chummy sports league there is; they have a team that is owned by casino magnates, for crying out loud. Cuban is finding that the world of sports ownership is essentially attempting to join a club that will not have you as a member.

In our world of social networking and high-definition television, Mark Cuban is the 1,000-pound gorilla in every room. But in the boardrooms of professional sports, he's just this punk Internet new money kid who doesn't understand how proper decorum and deals get made. And Mark Cuban is almost 50 years old! He's old enough to be Mark Zuckerberg's dad!

Cuban's hardly the only one to run into an old-money, new-money fight in the sports world. Paul Allen had his own issues after buying the Portland Trail Blazers and the Seattle Seahawks, and Research In Motion CEO Jim Balsillie has run into nothing but brick walls with his attempted purchase of the Pittsburgh Penguins and continued moves to try to move the Nashville Predators to Hamilton, Canada. These are new thinkers, with new ideas and new ways of doing business. This is not how professional sports operate, so they are shunned as radicals, or rejected all together. Most often, their idealistic notions of "changing the game" are crushed under the unceasing inertia of The Norm. Owning a sports team doesn't turn out to be nearly as fun as they thought. What is new and different must be crushed. This is why Mark Cuban will never own the Cubs, no matter how much money he waves in front of the Tribune Corp.

Every sports fan has daydreamed of falling into sudden riches, buying their own sports team and running it on their own whim. Now, all three of those things are equally unlikely; money just isn't enough anymore. The engines of finance and technology are driven by innovation; sports runs away from it, terrified. Mark Cuban will never be the next Ted Turner unless he changes his last name to Selig.