× Expand Esteban Whiteside

There’s a sad, unfunny because it’s too true, New Yorker cartoon by Paul Noth that has circulated steadily since it was published in 2016. In it, two sheep are looking at a campaign-style billboard of a wolf, with the slogan, “I am going to eat you.” One sheep says to another, “He tells it like it is.”

The cartoon gets to a weird duality about President Donald Trump. On one hand, he’s a liar: News organizations tracking his false claims reached a count of 15,413 by the end of last year. On the other, Trump can be uncomfortably truthful, as when he admitted to NBC News’s Lester Holt that he fired James Comey from the FBI because of the Russia investigation, or when he recently began firing government officials because they testified against him in his impeachment trial.

But the billboard also makes me think of Michael Bloomberg, whose 2020 campaign for president is getting renewed attention.

This week, audio clips surfaced in which the former New York City mayor essentially called minority neighborhoods crime-ridden and the young men who live in them criminals, and lamented the loss of the racist policy of redlining, which prevented African Americans from buying homes and building wealth until a 1968 law banned the practice. As I watched the clips spread and people respond to them, I felt like the rest of America was becoming acquainted with the Bloomberg I’ve long known.

Lawyers and officers used to joke that these defendants were arrested for “POP,” which meant “pissing off police.”

My first job out of college was as an investigator for the Civilian Complaint Review Board, an independent mayoral agency that investigates complaints of police misconduct. I worked there from 2002 to 2004, the first two years of Bloomberg’s tenure as mayor. It was the beginning of the heyday of stop-and-frisk, the practice that was found unconstitutional in 2013. In that case, the federal judge found that the New York Police Department used indirect racial profiling to stop black and Latino New Yorkers who wouldn’t have been stopped if they were white. Bloomberg defended the practice as late as last year, until he began apologizing for it in November.

The New York Civil Liberties Union has shown that the city’s police have stopped and questioned people more than 5 million times since 2002: at the height of stop-and-frisk in 2011, about 685,000 people, overwhelmingly black and Latino, were stopped. The NYCLU survey found that 90 percent of those stopped were completely innocent. Another analysis, by the Center for Constitutional Rights, found that while whites were stopped less often than blacks or Latinos, stops of white suspects were more likely to result in the seizure of a weapon, probably because they were more often based on truly suspicious behavior—that is, actual probable cause.

In 2012, The New York Times conducted a series of interviews with people about what it felt like to live under stop-and-frisk. These pervasive and abusive stops led to arrests of people even when the frisks turned up nothing. In one interview with the Times, a young man named Tyquan said that, if he demanded to know why he’d been stopped, the officers would respond, “If you’re going to talk back, we’re going to take you in. If you’re going to ask questions, we’re going to take you in.” He said he was stopped four or five times a month because he was often with friends, outside. “If you’re with a lot of people, you’re a suspect automatically,” he said. Eventually he felt that the only way he could get away from cops was to stay home. Which sounds a lot like being in prison.

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The CCRB cases I remember the most, and still think about, are these stop-and-frisk cases, and similar ones in which police officers stopped someone, overwhelmingly a young black man in a Brooklyn or Queens neighborhood, on the slimmest pretext. Sometimes, these men were chatting with their friends on the sidewalk, and an officer told them to move along because they were blocking pedestrian traffic, even when that traffic didn’t exist. At other times, the cops stopped and searched men who were standing and chatting too near a car, on the unfounded assumption they might be stealing it.

The worst involved those with kids. Someone on my investigative team had a case once in which a boy, I believe he was 13, was stopped inside his own apartment building and asked for identification. He was on his way to visit a friend in his own building. The stop was an allowed practice. Police officers had permission to patrol inside apartment buildings owned by the New York City Housing Authority, or any other privately owned building where the landlords invited them in. Which made it hard for this kid to simply visit a friend without a run-in with police. I’ve thought about him a lot over the years, and the ways his encounters with abusive authority may have shaped and changed the trajectory of his life.

On other occasions, I visited housing authority buildings and gone to the surveillance rooms that NYPD officers used to monitor residents. There were public spaces in these building complexes, courtyards and dilapidated playgrounds. But if anyone lingered too long, they were shooed away by police. What was the point, then, of the public spaces? What does it mean to have a home where the police can stop you any time?

For thousands of black and Latino New Yorkers, all this led to an oppressive feeling of living in a police state, of being constantly watched. Stop-and-frisk did lead to some arrests. Often, the charges were a constellation of such misdemeanors as disorderly conduct and resisting arrest; lawyers and officers used to joke that these defendants were arrested for “POP,” which meant

Esteban Whiteside

“pissing off police.” Whether guilty or not, any arrest traps the defendant in the complicated, time-consuming world of court hearings and trials. Often, just the accusation of wrongdoing is enough to lose a job or a home in public housing. Any arrest can lead to a downward spiral that’s hard to get out of.

What frustrated me most was that we could never do anything about these cases. The CCRB was tasked with investigating officers who had violated police procedure. But officers who stopped-and-questioned young people of color, and sometimes put them in jail, weren’t violating procedure. That was the procedure. That’s what Bloomberg admitted in the audio clip of the Aspen Institute question-and-answer session that surfaced this week.

Stop-and-frisk is a policy that led directly to the mass incarceration of black and brown men and women, one that has decimated communities and separated children from their parents. It is family separation by another name, happening on a slow, daily schedule in many American cities instead of in crowded facilities at the border. Bloomberg did not invent this policy, but he was a champion of it; in power he enacted it. The police practices under Bloomberg’s NYPD harmed people. One of the most heartbreaking stories was that of Kalief Browder, who was held at Rikers Island for three years without a trial, where he was abused and depressed. He committed suicide in 2015.

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The Bloomberg administration’s violations of the Fourth Amendment rights of New Yorkers are no less serious than Trump’s unconstitutional practices. If the images of young Latino immigrants in cages at the border trouble you, there is no reason to vote for Bloomberg. If Trump’s dismantling of any sense of justice in this country troubles you, there is no reason to vote for Bloomberg. Bloomberg treated communities of color as inherently criminal, and that broke families apart and traumatized children.

Ultimately, most of Bloomberg’s shortcomings as mayor stem from his philosophical and governing commitment to policies that perpetuate racial inequities. Stop-and-frisk was the most obvious, but as mayor he also failed to stem the loss of affordable housing in the city, and presided over one of the most segregated school districts in the country.

But unless there have been radical changes in the way Bloomberg thinks about power, I’m not sure the practical effect of his administration would be dramatically different from a Trump administration for many minority communities.

Bloomberg has risen in some polls recently, as in my home state of Arkansas, where he leads the Democratic field by 1 percentage point. He’s spent advertising money here and visited, focusing on issues like climate change. This has filled a vacuum: voters know almost nothing else about him, and no other candidates have a similar presence in the state. He touts his technocratic performance as (a Republican, then an independent, and fundamentally conservative) mayor of a large city as a beacon of hope, a mid-way choice for people who don’t like Trump but who fear the Democrats are moving too far left. Anyone is better than Trump, the thinking goes, and we shouldn’t nitpick little differences between candidates who promise to oust him. I have many Bloomberg-curious friends.

A Bloomberg candidacy would appease people most upset about the obviousness of Trump’s racism, the way he wields it with uncomfortable candor, the unseemliness of it. But unless there have been radical changes in the way Bloomberg thinks about power, I’m not sure the practical effect of his administration would be dramatically different from a Trump administration for many minority communities.

Electing Bloomberg is simply putting the wolf back in sheep’s clothing. Should he become the Democrats’ nominee, it would show too many people learned the wrong lessons from Trump’s years: It would put a veneer of respectability back over the deep, structural problems this country has. Those problems would still be there, destroying families and building pressure on many Americans, waiting to erupt.

Bloomberg has better positions on some issues, like gun control and climate change. As a billionaire philanthropist, he has campaigned for action on these causes; that is the role he should continue playing. On stop-and-frisk, he needs not just to apologize but to atone, and he needs to do that regardless of his campaign. The Democratic field is wide and varied. Bloomberg should stay out of it, where he belongs.