It’s not as if there was no approach available for a candidate like Bloomberg to take. He might not have the charisma or practiced on-camera moves of a longtime politician, but he certainly had options, and even strengths. I suspect that anyone who watched that debate with experience as a political operative—myself included—had a sense of what Bloomberg had to bring to this first debate.
Fundamentally, the challenge for Bloomberg was to seize the terrain of the debate; not just to acknowledge an error on stop and frisk, but to acknowledge that he (like many men of his generation) was all too comfortable with talking about women that was unacceptable—not just now and then. He had to know that lame assertions that he put women in positions of influence would not come close to answering the years of insults and crude jokes—but that was exactly the defense he offered. He had to know that simply asserting that he was the only one to build a business—true as that is—may not exactly be a line to set hearts beating faster in the Democratic primary. He had to know that every answer had to be shaped by a common theme: I’ve said and done things I am not proud of; I share with everyone on this stage a record of things I’m proud of and things I wish I’d done differently—but if you judge me by what I have done, and by how much Trump fears me, I am the right person to run.