Which One's The Crackpot? Which One's The Lesbian? Know Your Rickettses, The Politically Active Cubs OwnersS

The newspaper headlines make it seem like the Chicago Cubs owner is up to no good. "Cubs Owner Ricketts' Anti-Obama Ad Proposal Risks Stadium Growth." "Report: Emanuel 'livid' with Cubs owner after soliciting Jeremiah Wright attack ad proposal." Sounds like this Mr. Ricketts has really vexed some folks.

But wait a second! Tom Ricketts, the Cubs' chairman, seems like a cool guy. He rides the train, like working folks do—why would he try to smear Barack Obama with a race-baity message that didn't work back in 2008?

As people who read past the headlines probably already know, it isn't Tom Ricketts trying to smear Obama but his father Joe Ricketts, who founded Ameritrade, the online brokerage, and made the family fortune. The family shares 95 percent of the Cubs, but they don't exactly share politics. Meet the Rickettses!

Joe Ricketts, patriarch: Seventy-year-old crackpot. Born in Nebraska, but he lives in Wyoming now, on a big ranch where he raises bison. He founded Ameritrade in 1975 and retired from the company last year. He's since thrust himself into The American Film Company, a production company that aims to make historically accurate movies. He also funded the Ending Spending Fund, a dumb-sounding organization that spent a lot of money in hopes of vanquishing Harry Reid in 2010, and he is now financing the super PAC that considered tossing the Reverend Wright shit at Obama again. (The proposed ad—since abandoned—was a tour de force of unintentional hilarity and featured both negro-baiting and gay-baiting.) He's also thrown in with Deb Fischer, the Palin-endorsed Tea Party hotcha gal who's running for Ben Nelson's old Senate seat in Nebraska. Joe has no involvement in the day-to-day operation of the Cubs, nor is he on the team's board of directors.

Tom Ricketts, scion: He's the oldest of the Ricketts kids and turns 49 next week. He's the chairman of the Cubs. He earned his B.A. and M.B.A. from the University of Chicago (all the Ricketts kids went to U of C). While there, he fell in love with the Cubs. The love grew even deeper—he once lived across the street from Wrigley and met his wife in the bleachers. Now he lives in the suburbs, in Wilmette, while running the Cubs and an investment bank, Incapital. According to OpenSecrets, he has one political donation to his name in the 2012 cycle—a $5,000 donation to the Major League Baseball commissioner's office.

Laura Ricketts, renegade: Laura's 44. She's on the board of the Cubs. She's the only girl in the Ricketts clan, the only lawyer, and the only open homosexual. She's a big fundraiser for Barack Obama, and she gave over $30,000 to the Democratic National Committee earlier this year. She founded a site called EcoTravel.com, which apparently exists but won't load on my computer, and also sits on the board of Lambda Legal, an advocacy group for gays, lesbians, bisexuals, and transgender people. She lives in Chicago. She's distanced herself from her father's plan, but Joe says his opposition to Obama has nothing to do with social issues.

Pete Ricketts, the suck-up: Pete's 47. He, too, is on the board of the Cubs. In 2006, he ran for one of Nebraska's U.S. Senate seats as a Republican, spending over a million dollars of his own money. He lost. Badly. He captured only 36 percent of the vote, while running on a fiscally and socially conservative platform. During his campaign, he spoke out against gay marriage. Asked to explain his views in light of his sister's sexuality, he would only say: "I love my sister. I disagree with her on this issue. What more is there to say?" Pete is the son who followed most closely in his father's footsteps: He worked at Ameritrade (as COO); the other Ricketts started their own ventures. Pete's also the only one to have been especially active in Republican politics. After his father left the board of the conservative American Enterprise Institute, for example, Pete joined it. He's on the Republican National Committee. He's stayed in Nebraska, even though the other kids have decamped for Chicago.

Todd Ricketts, the cool one: Todd's 42, the baby of the family. He's on the board of the Cubs. He lives in Chicago. He jokingly called himself "the rebellious one" because he didn't attend University of Chicago for undergrad—he went to Loyola University—and he dropped out of U of C's Booth business school before he finished his MBA. But as far as Ricketts siblings go, he's got cultural cred. He did an episode of Undercover Boss. He owns some bike shops and picks his kids up from school on a bike. He's on the Ameritrade board, but he's only on one committee. He gave a little money to three Republicans—Mitt Romney and Illinois Reps. Bobby Schilling and Adam Kinzinger—but he hasn't run for office.