At long last, Mike Bloomberg is experiencing the scrutiny that traditionally accompanies the prospect of electoral success. So far, the damaging information gathered by journalists and opposition researchers who’ve gone spelunking through Bloomberg’s past fits a pattern: The former New York City mayor’s record on issues related to race and gender is, to be charitable, unenlightened.

When asked about the claim that New York City’s controversial stop-question-and-frisk program disproportionately targeted minority neighborhoods, the then-mayor made no effort to disprove the claim. Indeed, he insisted that minority neighborhoods were not targeted by law enforcement enough. “[I]t’s not a disproportionate percentage of those who witnesses and victims describe as committing the [crime],” Bloomberg said in 2013. “In that case, incidentally, I think we disproportionately stop whites too much and minorities too little.”

“Ninety-five percent of your murders, murderers, and murder victims fit one M.O.,” Bloomberg added in 2015. “You can just take the description, Xerox it, and pass it out to all the cops. They are male, minorities, 16 to 25.”

Bloomberg’s racial antagonism is not limited to issues of crime and justice, either. He has also weighed in on socioeconomic issues that he imagines pertaining to black Americans. “There’s this enormous cohort of black and Latino males aged, let’s say, 16 to 25, that don’t have jobs, don’t have any prospects, don’t know how to find jobs, don’t know that the—what their skill sets are, don’t know how to behave in the workplace, where they have to work collaboratively and collectively,” the mayor told PBS in 2011. Bloomberg also bizarrely blamed the end of the discriminatory practice of “redlining”—a Depression-era routine in which federal agencies limited the capacity of banks to underwrite home loans to lenders in certain neighborhoods, de facto segregating them by race—for the collapse of the mortgage market in 2008.

Bloomberg’s cultural illiteracy is not limited to race. The 78-year-old businessman has been accused of speaking “crudely about women all the time.” Bloomberg privately settled a lawsuit in which it was alleged that he told one of his employees to “kill it” when he was informed of her pregnancy. He’s dismissed the issue of transgender rights as a debate centered on the notion that “some guy wearing a dress . . . can go to the locker room with their daughter.” There is even a book, The Portable Bloomberg, produced by Bloomberg L.P.’s former chief marketing officer for the candidate’s 48th birthday, which is replete with quotes from Bloomberg that stretch the bounds of decency—not just in our enlightened age but even in 1990 when that record was compiled.

These are not manufactured issues. Bloomberg’s facility for reckless rhetoric and noxious generalizations could eventually consume enough media bandwidth to overcome the avalanche of money he’s poured into his candidacy’s paid media campaign. But it isn’t just the candidate’s benighted conception of what constitutes not just social enlightenment but basic propriety that could scuttle his campaign. His penchant for being a jerk about it would do that.

Outside the hermetic confines of progressive social-media networks, the general public (Democratic primary voters included) is more forgiving of a nearly 80-year-old’s conception of what constitutes socially conscious thought. Cancel culture, while formidable, is survivable. Infractions against modern standards of civil discourse and even basic decency are often forgiven, but only so long as the offender expresses some measure of genuine contrition. Here, Joe Biden’s experience is instructive.

From the earliest days of his campaign, Biden’s opponents unleashed a barrage of attacks on the former vice president’s multiplicity of sins against progressive social orthodoxy. His critics held him responsible for what they perceived to be Anita Hill’s mistreatment during Supreme Court Justice Clarence Thomas’s confirmation hearings. They claimed his willingness to work with the segregationists in his party was evidence of racial intolerance. They speculated that Biden’s intimate behavior around women represented a cardinal sin against the post-#MeToo era’s codes of interpersonal conduct. They insinuated that Biden’s invocation of “gay bathhouses” to describe the LGBT lifestyle exposed latent bigotry. But none of this had any effect on Biden’s support in national polls. What eventually did undermine his viability was something much more conventional: losing in the early states where his base of support was critically underrepresented.

What distinguishes Biden from Bloomberg is the latter’s apparent inability to evince sincere remorse. What Biden’s critics never fully appreciated was the extent to which the former vice president weathered these controversies not just because his habitual misstatements earned him the benefit of the doubt but also because of his willingness to own up to mistakes. Biden spent the better part of the last year apologizing for his conduct. And while Bloomberg has confessed to harboring some “regret” for the “unintended pain” stop-and-frisk caused his constituents, the conspicuously recent timing of his apology after years of stridently defending the practice betrays the apology’s insincerity.

Like Biden, Bloomberg’s relatively strong performance among African-American voters both in this primary race and during his tenure in office as New York City’s mayor suggests a willingness to look past his penchant for indecency and racial antagonism. Like Biden, Bloomberg is not going to be undone because he’s not woke enough. But there is a liability here, and it won’t be neutralized by being irascible and defensive. If Bloomberg cannot summon some sincerity, the efforts to highlight his chronic boorishness might work in a way the attacks on Biden did not.

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