Cathie Black and her husband, Tom Harvey
Mayor Bloomberg doesn't mind picking a fight. But after nine years in office, he should have learned to pick his battles.
He has famously tried - and failed - to build a West Side football stadium, charge tolls into lower Manhattan and turn the Kingsbridge Armory into a huge shopping center.
There was no shame in those losses, though. No matter what you thought of them, they were legitimate ideas with solid backing that deserved a hearing.
Trying to put a magazine executive in charge of the city schools is a different story.
Bloomberg may have been the only person in New York who didn't see a downside in naming Cathie Black to be schools chancellor.
"He was thinking about an out-of-the-box candidate who would carry on Joel Klein's legacy and be sort of a maverick," said consultant George Arzt, a longtime student of New York mayors.
"I'm sure in his mind he thinks that this is right for the city," Arzt said. "But there were no other candidates interviewed - and it showed."
Even Black's supporters knew a boarding-school mom with a corporate résumé would be a tough sell, no matter how strong a manager she is.
Bloomberg's inner circle could have told him that - had he bothered to tell them about Black before he made up his mind.
"He went into this by himself, and in fact it was revealed that the emperor had no clothes," said Baruch College political scientist Doug Muzzio.
The mayor's team could have quietly reached out to state Education Commissioner David Steiner to see how he would react, or to at least give him an early heads-up.
Instead, the aides who get paid to build support for his controversial ideas - like lifting the charter school cap or extending term limits - were playing defense from the start.
Public school parents understood the problem of a boss with no experience, and 62% of them told a Quinnipiac University poll they didn't want Black.
Bloomberg thinks he knows better - but six of eight experts on the state education commissioner's panel agreed with the parents.
Three years ago, the mayor said, "I have always joked that [the difference between] having the courage of your convictions and being pigheaded is in the results."
The results are in. As he looks to salvage Black's nomination, he should look in the mirror, too.