Having worked on Michael Bloomberg’s first campaign for mayor in 2001 as a policy adviser, I have an appreciation for the difficulties the super-rich face when seeking public office. Motives are questioned. Folks wonder if they’re bored and looking for a new toy to play with. And the capacity for empathy is questioned. Folks not only worry that someone so wealthy won’t be able to relate to everyone else, but also that said person won’t give two hoots about the poor and will govern against them. But as we’ve seen, Bloomberg’s Big Apple mayoralty has been a success.

Which brings me to Mitt Romney. He’s not nearly as wealthy as Bloomberg. But he’s by far the richest man in the hunt for the Republican nomination for president. Unlike Bloomberg, who had no political experience when he first ran for mayor, Romney has had plenty. He was governor of Massachusetts, where Bloomberg was born and raised. He ran unsuccessfully for the U.S. Senate in 1994 and the GOP crown in 2008. Both were good training grounds and laid the foundation for Romney’s incredibly disciplined campaign. A discipline that seems to have escaped his mouth, which has a bad habit of feeding the negative and out-of-touch impressions of him.

Dana Milbank zeroes in — as we all have — on Romney’s “I like being able to fire people” banana peel. Yeah, yeah, yeah, when read in context, Romney makes a lot of sense. Unfortunately, because he’s shown a willingness to cut and paste with impunity, no one’s going to care. Damage done.

But there are other examples.

June 16. Tampa, Fla. Coffee shop

“I should tell my story,” Romney said. “I’m also unemployed.” He added, “I may be unemployed for longer than I’d like.” (As reported by the New York Times and TownHall.com)

Aug. 11. Des Moines. Iowa State Fair

“Corporations are people, my friend,” Romney said.

Some people in the front of the audience shouted, “No, they’re not!”

“Of course they are,” Romney said. “Everything corporations earn ultimately goes to people. Where do you think it goes?” (As reported in The Post)

Dec. 10. Iowa. GOP debate

“Rick, I’ll tell you what, 10,000 bucks?” Romney said. “$10,000 bet?”

(As reported in The Post)

Jan. 8. Rochester, N.H. Rally

“I know what it’s like to worry whether you’re gonna get fired,” he told about 600 people in an opera house. “There were a couple of times I wondered whether I was going to get a pink slip.’’ (As reported by the Boston Globe)

Bloomberg never tries to pretend he’s not rich, much to the annoyance of many. But in discussing his legendary philanthropy, the mayor has often said that he’s been more successful than anyone has a right to be. Bloomberg has never forgotten his humble roots. Perhaps that’s Romney’s problem. There’s nothing humble about the former Massachusetts governor’s roots.