He was born in Evanston, grew up in Winnetka (went to New Trier High School) and got his start in politics as Congressman from the North Shore, so it shouldn't be too surprising that Donald Rumsfeld developed a love for the Chicago Cubs.
He is a member of the Emil Verban Society (a group of Washington-based Cubs fans).
In the book "The Zen of Zim," Don Zimmer tells the story about the day he met Rumsfeld when the Yankees were invited to Washington.
"Roger Clemens arranged for Joe Torre, me, and a half-dozen other Yankee people to go to the Pentagon after the September 11 attacks. I remember we were sitting in the dining room where they were about to serve lunch when all of a sudden one of the Marine guards shouted 'ATTENshun!' I look behind me and into the room in walks Donald Rumsfeld, the Secretary of Defense. Everybody stiffened up. We all got in line to introduce ourselves to him, but when I got up to him he said: 'Oh I know who you are! I know you from Chicago!' He told me he lived in Chicago when I was managing there and he watched all the games on TV."
In 2003, when the Bush Administration shuffled the chain of command regarding Iraq's reconstruction, and Rumsfeld was asked why he wasn't consulted about that decision, he replied: "With the Chicago Cubs in the play-offs, we can find something more important than that."
In 2004, Rumsfeld appeared on US-99 radio (with John Howell & Ramblin Ray Stevens) and talked about his favorite team, the Cubs. Here's an excerpt from the Department of Defense transcripts:
SEC. RUMSFELD: Oh, it’s just glorious in Chicago.
JOHN: Don’t you wish the Cubs were home today? You could slide by there, see the 7th inning stretch?
SEC. RUMSFELD: I checked to see if they were. [Chuckles]
JOHN: [Chuckles] So as a Cubs fan, let’s ask you quickly about the Cubs. I now we have limited time with you, but it’s a big subject in this town. And since you’re a lifelong Cubs fan. Now we’re talking to you on Friday. We’ll replay this interview on Monday. Do you think Greg Maddux is going to win his 300th this weekend?
SEC. RUMSFELD: Absolutely. He’s due. He’s ready. [Chuckles]
We don't get into politics in this feature, we only report who loves the Cubs. Agree or disagree with him about his decisions in office, that's up to you. But obviously our former Secretary of Defense has the same disease that we have: He is stricken with "Cubsitis".
