The stop-and-frisk apology video offers one kind of playbook. “I know I can’t change history,” he concludes, “but what I can do is learn from my mistakes…” He then promises an ambitious campaign to “right the wrongs of institutional racism wherever they exist.”

Judged rhetorically, Bloomberg’s statement about stop-and-frisk ranks pretty high. He does not report to the favorite passive tense of many politicians: “mistakes were made.” He does not apologize “to those who may have been offended.” It’s a presentation that uses words like “mistake” or “wrong” more often in two and a half minutes than Bloomberg has likely used in any given six-month period of his life.

In some circumstances, this video, combined with the army of endorsements from black mayors, House members, and other officials, might have been enough. But as a candidate heading into his first big public moment, it’s hard to imagine it will protect him on the debate stage.

For critics like New York Times’ columnist Charles Blow, Bloomberg’s more recent apologies ring hollow. “No amount of Democrats’ anti-Trump fear and panic will ever erase what Bloomberg did,” Blow writes. “Democrats have a field of fascinating candidates. Many have some crime and justice issues of their own, but nothing approaching the scale of Bloomberg’s racist policy.”

It's safe to assume that Bloomberg’s opponents will try to force some of these issues once he's on the same debate stage with them. Elizabeth Warren has already weighed in on another problematic Bloomberg statement, when he suggested that the end of racially discriminatory “redlining” helped lead to the 2008 financial meltdown: “[Bloomberg says] that crisis would not have been averted if the banks had been able to be bigger racists," she said at a town hall in Arlington, Virginia. “And anyone who thinks that should not be the leader of our party.”

His record with women is another place he'll need to practice the art of the fast backwards walk. What emerged from decades of comments—some of them gathered in a short book prepared by a Bloomberg worker—reveals an approach to women right out of “Mad Men” and “Liar’s Poker.” When he talks about the Bloomberg terminals that were the source of his immense wealth, he jokes that it can even perform oral sex, “which puts a lot of you girls out of business.” He suggests that women line up to give a colleague oral sex as a wedding present. He “quips” that “if women want to be admired for their brains, they’d go the library instead of Bloomingdale’s." Whether he actually did tell a pregnant employee to “kill it”, there are a host of comments which show that he regarded pregnancy as a burden to his business, and made little or no effort to accommodate expectant mothers.

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So far, Bloomberg's apology effectiveness seems mixed. On the law-and-order front, Bloomberg has one significant asset that often makes the difference between riding past a mistake and collapsing under its weight: forgiveness and support.

Even as the story of Bloomberg’s comments surfaced, he was winning the support of members of the Congressional Black Caucus, like New York’s Gregory Meeks; from the executive of Wayne County, Michigan; a host of present and former Mayors, like Philadelphia’s Michael Nutter. On Friday, pollster and strategist Cornell Belcher signed on to the campaign. Bloomberg’s foes may believe (with reason) that many of these endorsements are a quid-pro-quo payback for years of political and philanthropic dollars that have flowed from Bloomberg to campaigns and causes, but it is hard to imagine that Bloomberg’s foes will aim that kind of charge at major figures in the Democratic Party’s key constituency.

So when (not if) Bloomberg’s newfound contrition on this issue is challenged, it will be a simple matter for him to argue: “if all these African-American leaders can accept my apology and support my campaign for President, that’s a more eloquent answer than any I could offer.”

Less clear is how that will go down on the gender front, where the case against Bloomberg is based on long patterns of behavior and not just a single policy. The Bloomberg campaign has already posted a response akin to the stop-and-frisk strategy: a video of women who have worked in his company for years and praise him for empowering and respecting women.

Viewers are entitled to a hearty dose of skepticism here. The African-American politicians who embrace Bloomberg’s campaign may well have been influenced by his financial support of their policies and politics. But they at least are not in his direct employ.

Moreover, there’s a common thread that runs through many of Bloomberg’s comments: It’s a sense of arrogance, of privilege that does not to concern itself about the consequences of his behavior. You can see that in the just-revealed comments about the simplistic demands on farmers, compared with the work of the present that demands more “grey matter.” (He says he was talking about farmers of the distant past.)

Right now a regiment of current and former political operatives are conjuring up notions about “how Bloomberg will respond.” But I’m not sure the playbook offers much guidance here. It is possible that the sheer volume of Bloomberg’s messages, and the support of constituencies wounded by his comments, will be enough to override the storm—especially if there is growing condition that Bloomberg is a) the only one who can stop a disastrous Sanders nomination and b) the only one who can beat Trump.

It may be, however, that Bloomberg will have to offer up something very different: a frank acknowledgement that he has behaved like a jerk for much of his life. When the first questions come during the debate—and they will certainly be the first aimed at him—he may have to roll out some humility, language like “judged by my words and some of my deeds from another time, I would not deserve your vote.” He may even have to recognize that his enormous success, and his enormous wealth, blinded him to the impact those words and deeds had on others.

He may also decide to employ a piece of political “judo”, turning a weakness into a strength. It would be both accurate and perhaps even appealing to hear a candidate say: “I am not a warm guy who wears emotions on his sleeve. What I try to do is to figure out what needs to be done to make life better—for the victims of gun violence, for all of us threatened by climate change, for an economy where there are not enough roads into a decent job. I will not always agree with your ideas; and yes, I’ve been too dismissive, too arrogant with what I’ve said about those I’ve disagreed with. But take a look at what I’ve done.” (And should Sanders or Warren assail the idea that an enormously wealthy candidate should represent the party, there are nine initials that should answer that criticism: FDR, JFK and RFK, three figures of great wealth and privilege who are still among the most revered of Democrats.)

I don’t know whether it is in his character to speak such words as a matter of conviction rather than as a matter of strategy. And maybe the specter of the current president, whose arrogance and narcissism are boundless, makes Bloomberg’s liabilities pale by comparison. But with first debate just hours away, and with Super Tuesday almost upon us, the capacity of Bloomberg to eat a large helping of crow could well be the most important question of the campaign so far.