Lately we’ve been engaging in the pastime of cataloguing celebrities who travel to Cuba. Here’s another.

Rahm Emanuel is the kind of political professional whom even his own friends don’t particularly care for. A longtime fixture of that grubbiest of all American political machines, the Cook County Democrats, he’s brash, rude, obnoxious. (Pick your synonym.) And yet, thanks to his native wiliness and (increasingly) his high-level connections, he’s moved from triumph to triumph.

Born in Chicago, Emanuel attended Northwestern, worked on the 1992 Clinton campaign and then in the Clinton White House, made over $16 million for four years’ work at an investment bank (despite having no background whatsoever in banking), and was a director of Freddie Mac during a major scandal. (According to ABC News, he and his fellow board members “misreported profits by billions of dollars in order to deceive investors,” thereby helping to precipitate the world financial crisis of 2008.) After spending six years in Congress (where he was head of the Democratic Congressional Campaign Committee), he was appointed Obama’s first chief of staff, then ran successfully in 2010 for mayor of the Windy City – a position he now holds.

When Emanuel took over the reins of power in Chicago, the city was a nightmarish mess. He hasn’t helped. The toddlin’ town remains notorious around the country, in fact the world, for its high crime level – and, in particular, its gang killings. Its public education system is a scandal and an embarrassment. Its bond rating has sunk to near-junk bond level. Most recently, Emanuel has faced mounting criticism for his incompetent handling of the judicial aftermath of a police shooting that took place in October of last year. Incompetence, indeed, seems to have become a hallmark of his tenure. 

But he doesn’t seem fazed by any of it. After five years of spectacular failure in the job of mayor, he clearly hasn’t learned humility. On the contrary, one gets the distinct impression that he’s already working on his next step up the career ladder. A Senate seat? Perhaps even the presidency? “What you see in Rahm Emanuel is what you get, and what you get is raw ambition,” wrote Chicago author Joseph Epstein earlier this year in an acid profile of the mayor. Some public servants actually do think of themselves as servants of the public. Not Emanuel. This guy, observed Epstein, “is in business for himself.” Another pol in his current position might at least try to tamp down the insolence, lose the swagger; alas, the worse things get for Emanuel, the more often he seems to dial his legendary arrogance up to a 10. 

Case in point: at a breakfast event in early December, Mike Allen of Politico spent almost an hour interviewing Emanuel in front of an audience. Then Allen happened to mention something that Emanuel had told him backstage: this year, the mayor and his family were planning to spend the holidays in Cuba. Why Cuba? Allen asked.

It seemed a relatively innocuous question. But instead of immediately answering it, Emanuel launched into Allen, expressing his irritation at the reporter’s disclosure. “Well, first of all, thanks for telling everybody what I’m going to do with my family,” Emanuel said. “You had a private conversation with me and now you decide to make that public. I really don’t appreciate that, for one, I really don’t.”

“I’m sorry,” Allen replied. “I didn’t know that wasn’t known.”

After upbraiding Allen a bit more, Emanuel got around to responding to Allen’s query. He wants, he said, to expose his kids “to other cultures, other parts of the world, and one of the things that we want is for our children to know that the world has people of different faiths, different backgrounds, with different ways of living and coping with similar situations.” He noted that he and his wife, Amy Rule, had previously taken their children to Uganda, Kenya, Zambia, Vietnam, and Laos.

Aha! This list of Emanuel family vacation spots explained everything. Obviously, Emanuel likes to take his children to places that are even more horribly governed than the city of Chicago – places with even higher crime rates, lousier schools, crummier economies, more broken-down infrastructure, and more outrageous levels of government corruption, graft, malfeasance, and all-around venality. Get it? This way they’ll actually return home thinking that their father’s done a terrific job in Chicago. Kind of touching, isn’t it?