A Politico Playbook breakfast event in Chicago on Wednesday got real awkward, real fast, when host Mike Allen asked Mayor Rahm Emanuel about a very sensitive and timely subject.

I’m talking, of course, about the Emanuel's plan to take a family trip to Cuba this holiday season.

What, you thought I was talking about that whole cop-charged-with-murder, police-chief-fired thing?

Nope. What set off Emanuel was a seemingly innocuous inquiry from Allen, Politico’s chief White House correspondent and Playbook author, about world travels and why he picked Cuba this year.

“Well, first of all, thanks for telling everybody what I’m gonna do with my family,” Emanuel replied, sarcastically. “I really — you just had a private conversation with me, and now you decided to make that public. I really don’t appreciate that, for one. I really don’t.”

Emanuel went on to give a thoughtful response about the purpose of travel — namely that his children “get to be exposed to other cultures, other parts of the world.”

But he quickly returned to his displeasure with Allen: “This year — if my wife doesn’t kill me now because of what you just did — we will take our kids to Cuba to be exposed to that culture, in the same way they’ve been to India and the same way they’ve been to Uganda, Kenya, Zambia, Chile and Vietnam and Laos. I can’t wait — can you give me your cell number? Because I’d like you to listen to Amy.”

“Uh, I apologize for that,” Allen responded.

“I don’t know if you know this,” Emanuel added. “It’s not going to work.”

Okaaay ... lots to digest here.

Emanuel is under a lot of pressure these days, so maybe we should cut him a little slack for being short-tempered at the moment (or rather, more short-tempered than usual). But come on. Allen didn’t spill the beans on something super private here, and Emanuel hasn’t treated the destinations of previous family vacations like state secrets.

Also, Emanuel kinda dissed his wife, suggesting she will be furious and possibly homicidal when she finds out that the Cuba trip is public. He asked Allen to take the punishment for him and warned him that no amount of explaining will get him off the hook. What's up with that?

Then there’s this little twist: Just a couple days ago, Allen felt the need to defend himself after Gawker published an old e-mail in which he offered Chelsea Clinton pre-approval of the questions for an event much like the one in Chicago on Wednesday.

“I said I'd agree to the questions in advance,” Allen wrote in Monday’s Playbook. “I have never done that, and would never do that. Politico has a policy against it, and it would make for a boring event. As you know from attending our events (or can tell by clicking on any of the videos on our website), they’re spontaneous, conversational and news-driven. Without stunts or grandstanding, we challenge guests to address newsworthy topics, and to be original, relevant and revelatory. A scripted back-and-forth would be a snore.”

Well, the exchange with Emanuel sure didn’t look scripted, and it certainly wasn’t a snore. In a weird way, it might actually be the best thing that could have happened to Allen this week. After the Gawker thing, he risked looking too friendly with Democrats. The sit-down with Emanuel — President Obama’s former chief of staff — was anything but friendly.