At a public forum in early December, embattled Chicago mayor Rahm Emanuel gave the political world a glimpse of his notoriously short temper. Veteran Politico reporter Mike Allen had made the unpardonable error of revealing the former White House chief of staff’s plan to take his family on a winter getaway to Cuba. Emanuel, under fire for his handling of a video of 17-year-old Laquan McDonald being shot to death by Chicago police, tore into the unsuspecting journalist. “Well, first of all, thanks for telling everybody what I’m going to do with my family,” Emanuel said, leveling his icy glare at Allen. “You had a private conversation with me and now you decide to make that public. I really don’t appreciate that.”

It was classic Emanuel, blunt and bullying, and it had its intended effect. Allen was left to sputter; the audience was in no doubt about Emanuel’s status as Top Dog. The only thing missing from the awkward moment was the mayor’s legendary profanity. But the exchange raised an obvious question, at least for those outside of the mainstream media: what is a high-profile, office-holding, professional politician in the middle of a potentially career-ending crisis doing vacationing in—of all places—Cuba?

You don’t have to be on the left to be curious about Cuba. If you’re the kind of person who travels the world for sport, the long-forbidden island nation surely leapt to the top of your must-see list when Barack Obama opened up relations with the Castro regime earlier this year. For better or worse, Cuba is a legitimate tourist destination. But most Americans don’t have the money or the time for a holiday in the sun, much less a sightseeing trip to a brutal Communist dictatorship. Seven years after the financial crash, average Americans are only now seeing their wages and home values start to grow. In violence-plagued Chicago, 35 percent of respondents to a recent survey said they aren’t building wealth by either saving or investing. A 2015 Brookings Institution report showed that Chicago’s recovery has been much slower than that of most other cities.

Politicians are entitled to vacations, but smart politicians take smart vacations. When Rudolph Giuliani was mayor of New York City, he often escaped to the Hamptons on the eastern end of Long Island—near enough to get back to deal with an emergency. His successor, Michael Bloomberg, a billionaire, spent weekends at his home in Bermuda, but rarely took longer trips unrelated to his job running the city. The reason for a mayor to keep his vacations local is no more complicated than Murphy’s Law. In large cities like New York or Chicago, something always goes wrong when you least want it to.

Now, Emanuel’s worst nightmare has come to pass. Protests against his handling of the McDonald killing intensified during the Christmas holidays. Over the weekend, Chicago cops shot and killed two more people, described by the New York Times as “a 19-year-old man with possible mental health problems and a . . . 55-year-old bystander.” An already on-edge city now moves closer to full-scale revolt against its political leadership. In an attempt to head off criticism, the absentee mayor proposed—from Cuba—changing the way cops are trained to deal with the mentally ill. That proposal won’t satisfy critics. On Monday, Al Sharpton called for Emanuel’s resignation. Emanuel’s spiraling troubles with Chicago’s black community could soon lead the media to turn against him. And that might encourage President Obama, the one man in America who could conceivably throw Emanuel a political lifejacket, to distance himself from his former chief of staff.

Famous for advising the president that he shouldn’t let “a good crisis go to waste,” maybe Rahm Emanuel should heed instead the Obama administration’s foreign policy mantra: Don’t do stupid stuff. Of course, Rahm being Rahm, he might prefer the wisdom in its original, saltier version.

Photo by Scott Olson/Getty Images


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