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As political donors, the Chicago Cubs' owners swing for the fences

Rick Newman
·Senior Columnist

Baseball fans probably hope they can escape presidential politics during this year’s World Series, which starts Tuesday night between the Chicago Cubs and the Cleveland Indians. It just so happens that the Cubs, however, are owned by one of the country’s most politically active families—with millions in donations to both sides of the aisle.

The Ricketts family purchased a 95% stake in the Cubs in 2009, when the Tribune Co. decided to sell the team. Joe Ricketts, 75, is the founder of the online brokerage now known as TD Ameritrade (AMTD), which just announced plans to purchase rival Scottrade, for $4 billion. Ricketts, a self-made billionaire, isn’t involved in running the Cubs, but his money largely financed the purchase of the team.

Ricketts is a long-time megadonor who has given at least $32 million to Republican candidates and causes since 2010, according to a Yahoo Finance analysis of federal data. But a dismal winning percentage of late has kept him out of post-season play. Ricketts and his wife Marlene initially supported Wisconsin Gov. Scott Walker in the current presidential race, donating $5 million to his super PAC last year. (They got most of that back after Walker dropped out in September of 2015.) While supporting Walker, the couple also spread their bets around, making smaller, five-figure donations to super PACs supporting Jeb Bush, Ted Cruz, Marco Rubio and Lindsey Graham.

As their preferred candidates fell to Donald Trump in the primary elections, Joe and Marlene Ricketts became the biggest donors to an anti-Trump super PAC called Our Principles, which tried to stop Trump while Cruz and John Kasich were still in the race. Once that effort failed and Trump became the nominee, pressure mounted on the Rickettses to get behind the Republican candidate. In September, they finally agreed to contribute $1 million to a group supporting Trump.

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While Joe Ricketts isn’t directly involved with the Cubs, his four children—Tom, Pete, Todd and Laura—are all board members, with Tom being the club’s chairman and day-to-day chief. Tom is the least politically active member of the clan, with less than $100,000 in political donations since 2010. The biggest recipient has been Major League Baseball’s political-action committee, which donates to both Republican and Democratic politicians who favor its interests. Tom Ricketts’ wife, Cecilia, donates occasionally as well, with her biggest contribution, $7,800, going to a group called Winning Women that supports pro-choice candidates of both parties.

Laura Ricketts, the third of the four Ricketts kids, is the political opposite of her father. She’s a Hillary Clinton fundraiser who has given more than $2.2 million to Democratic and liberal causes since 2010. Her biggest gifts have gone to L Pac, which donates to candidates supporting gay rights. She’s also given $200,000 this year to the Hillary Victory Fund, a pro-Clinton super PAC.

Pete Ricketts, the oldest of the four kids, is the governor of Nebraska, where Joe and Marlene raised their family. That makes him the only Ricketts kid not living in Illinois. He’s a reliable donor who has given $434,200 to dozens of GOP candidates since 2010. (His wife, Susanne Shore, has given $6,700 to Hillary Clinton, according to federal records.) Todd Ricketts, the youngest child, is a bike-shop owner and CEO of a political group called Ending Spending, which was founded by his father and mostly supports Republican candidates seeking to rein in the federal budget.

The owners of the Cleveland Indians, the Dolan family, play small ball compared with the free-swinging Ricketts. Larry Dolan, an 85-year-old retired attorney, bought the Indians in 1999, and his son Paul is now CEO. The Dolans and their spouses have donated only about $160,000, combined, to political candidates and causes since 2010. Nearly half of that money went to the MLB PAC. Other modest Dolan donations have gone to Ohio politicians including Gov. John Kasich and Sen. Rob Portman, both Republicans, and Sen. Sherrod Brown, a Democrat. As people in any sport know, there’s more than one way to win.

Rick Newman is the author of four books, including Rebounders: How Winners Pivot from Setback to Success. Follow him on Twitter: @rickjnewman.