Bill Murray won $5 off Obama playing golf, in the Oval Office, wearing a Cubs jersey

President Obama is a fan of the Chicago White Sox, and if you want to see a White Sox fan reluctantly root for the uptown rivals, watch Obama's face before saying he hopes the Chicago Cubs win the World Series on Monday's Jimmy Kimmel Live. "I am rooting for the home town team, even though it is not my team," Obama said, pointing out how happy Cubs fans are after their 108-year drought. "White Sox got their championship a little over 10 years ago, so we're feeling okay." Kimmel noted that Bill Murray "may be the premier Cubs fan of all the Cubs fans," and that he crashed the White House while he was in Washington, D.C., to accept the Mark Twain Prize for American Humor.

"He came into the Oval Office in a Cubs shirt," Obama said, "and I don't usually allow that to happen." Most people wear a shirt and tie, he said. "It was Bill Murray, so I figure, all right, no tie, but don't rub it in with the Cubs jersey on." "I'm amazed by him, because he pretty much does anything he wants," Kimmel said, and Obama illustrated that with a little story.

Murray agreed to do a small social media bit on enrolling in health care, and he and Obama "thought of a little skit, and we decided we were going to putt on the carpet in the Oval Office" into a glass, Obama said. "And he won repeatedly. I mean, he kept on hit— the glass was rigged." "That's happening a lot lately," Kimmel said. "I was a little frustrated," the famously competitive Obama said, "and what makes matters worse, then he's giving me tips about putting ... But he took money from me, and I paid him $5. So basically, the whole business was a disaster." Kimmel's only response was, "You have money, like, do you have any money with you right now?" And it turns out that was a good question. Watch below. Peter Weber

Subscribe to The Week

Escape your echo chamber. Get the facts behind the news, plus analysis from multiple perspectives.

SUBSCRIBE & SAVE

Sign up for The Week's Free Newsletters

From our morning news briefing to a weekly Good News Newsletter, get the best of The Week delivered directly to your inbox.

From our morning news briefing to a weekly Good News Newsletter, get the best of The Week delivered directly to your inbox.

Sign up