There’s probably no man alive better suited to put Donald Trump on the couch than that other self-promoting “Bonfire of the Vanities” character who dominated the tabloids in the 1980s: Al Sharpton.

The two men are very different politically, of course, but they are — to an extent both quietly admit to friends — salt-and-pepper, Queens-Brooklyn doppelgängers. Back in the 1980s, while Trump was struggling with his casino business but prospering on the front pages of the Post and Daily News, Sharpton was a 309-pound street preacher who wore velvet tracksuits, gold rope chains and a Trump-like ambition to eventually gain real power.


Now, at half his ’80s weight and with tons less political baggage, Sharpton has succeeded in reinventing himself as a TV personality and a first-among-equals African-American community leader with President Barack Obama’s ear — and an iPhone full of emails this week from supporters of Hillary Clinton and Bernie Sanders begging for his endorsement before the South Carolina primary.

Sharpton has no intention of pulling the trigger immediately, though that could change if Clinton blows out Sanders in South Carolina this week; eight years ago, he took his time in “backing” (but not officially endorsing) Obama over Clinton in the primaries, claiming caustically that “Hillary Clinton has never done nothing for us” — a reference he says was meant to refer only to his organization, the Harlem-based National Action Network, but that others interpreted as a broader rebuke of her attitude toward blacks.

But he’s nothing if not acutely conscious of his leverage, and thinks it would be stupid (he uses the word “pre-emptive”) to throw away the influence he currently enjoys.

“Will I endorse sooner or later?” he asks. “Yeah.”





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But, as we sat in Sharpton’s small MSNBC office in Rockefeller Center for the latest edition of Politico’s “Off Message” podcast, the reverend’s mind was very much on Trump, whom he sees as a menace, but an amusing, familiar menace: a fellow outer borough hustler who’s not quite a friend, but certainly not an enemy.

“I think what he has said has been biased and bigoted, but I don’t know if Donald Trump is really a bigoted guy,” says Sharpton when asked about the reality star’s comments on Mexicans and Muslims.

And Sharpton knows exactly who the GOP front-runner reminds him of — and it’s not Benito Mussolini or Huey Long or George Wallace — it’s a black guy, a motor-mouthed, sprout-haired boxing promoter who befriended Sharpton and brought him into the glamorous, big-money world of Atlantic City prizefighting three decades ago.

“The best way I can describe Donald Trump to friends is to say if Don King had been born white he’d be Donald Trump,” says Sharpton with a broadening smile. “Both of them are great self-promoters and great at just continuing to talk even if you’re not talking back at ’em.”

The 61-year-old civil rights leader then launches into a crazy story. King and Trump were friendly, and King suggested the brash developer court Sharpton, in part to improve his relationship with Mike Tyson, who was close to the preacher at the time.

“Don King had me fly with him and Trump to Atlantic [City] in Trump’s helicopter, and it was one of the most memorable things in my life to sit on that big, black Trump helicopter … both of them talking nonstop, not listening to each other,” he recalls. “And I’m sitting there. It was probably the longest ride … I ever was on. Both of them shut me up. I haven’t been quiet since.”

When I ask Sharpton whether he actually likes Trump, he shrugs. “I mean, I don’t like what he’s doing. But I don’t dislike him. He’s the kind of personality that is hard to dislike. He’s entertaining, let’s put it that way. You’d have to be a New Yorker to understand him.”

And that’s when he gets to his keenest observation — the best assessment of Trump’s deepest motivations I’ve yet heard, and one that Beltway pundits who don’t understand the tangled psychological geography of the five boroughs miss: Trump may have been born with millions and erected huge buildings that bear his name, but he still feels the resentment of a gaudy, new-money outsider who has decided to burn down a Yankee establishment that always viewed him as a garish, grasping joke.

“Donald Trump was a Queens guy,” says Sharpton, who hails from Brooklyn’s Brownsville, the city’s toughest neighborhood, a collection of housing projects jammed hard between Queens and the Jamaica Bay swamps — and the scene of an all-out crack war in the 1980s and ’90s.

“His father was a successful real estate guy, but they were Queens guys. They were outer borough [and] had to break into the big Manhattan aristocracy. He was an outsider — rich, but an outsider. He was not part of the Manhattan elite. So, he always had this outsider feeling — us against them. So, in many ways, when I read people talk about, ‘Well, do you have a billionaire as a populist?’ He does feel like he’s one of the guys who was shut out.”

Then, in a hint of a kindred spirit, Sharpton says: “On the other side of the coin … I was shut out because of race. He was shut out because of geography and a number of other things. [It’s an] unforgiving environment, and a city that could easily swallow you up. Easily.”

Every time I write about Sharpton, many of my old friends in the New York press criticize me for not grilling him on the scandals of the past: the Tawana Brawley affair, his tax bills, allegations (which he denies) that he incited a deranged protester to start a deadly fire at a Jewish-owned clothing store in Harlem. But Sharpton’s come a long way, and Obama has elevated him as the pre-eminent leader of the black community, a role that he’s played with obvious relish during the 2016 primaries.

In the past couple of weeks, both Democratic candidates have met privately (and inconclusively) with him. Sanders sat with Sharpton in a window seat at Harlem’s legendary soul food eatery, Sylvia’s, even though the reverend is on a ridiculously Spartan diet consisting of four wheat toast slices and, a couple of times a week, fish. Clinton met with him, along with other civil rights leaders, at the offices of the National Urban League on Wall Street.

People close to Sharpton say he likes Clinton, and is probably inclined to endorse her — but he doesn’t quite trust her, wants to see how her sputtering campaign performs, and is intent on exercising maximum leverage on the issues he cares about most: community policing, sentencing laws and urban economic development. When I turn off the tape recorder, he says, “The minute you endorse, you become a surrogate and I want to be an advocate.”

Yet, as a black Brooklynite who grew up in the most racially combustible era in the city’s history, Sharpton is a little more skeptical of Sanders, who grew up in the same all-white, Jewish and Italian neighborhood in southern Brooklyn my family occupied for three generations. When I mention that I’ve been trying to get Sanders to talk on the podcast (so far unsuccessfully) about how growing up there influenced his racial views, Sharpton nearly jumps out of his chair.

“That conversation would tell me what he’s really — [what he] knows and is comfortable with about race. … I think Sanders has a good background,” he says. “But coming from New York, again, I want to know where, at home, you can show me your sensitivity to race in New York, where I know was a cesspool for bigotry, particularly in [those] years.”

On one hand, he gives Sanders a pass for citing the Wall Street plutocracy as the source of racial evils, and thinks the Clinton campaign’s attack on the Vermont senator as a color-blind, single-issue candidate goes a little too far. “I think that it’s — I won’t say ‘manufactured,’ but I think it’s exaggerated,” he says. “My argument to Sanders — which he has dealt with now — was that, if you close all the big banks and everything is brought down, that still doesn’t make us equal, given the race gap in employment, given the race gap in wealth and property ownership. You’ve got to address race.”

He’s far less forgiving of Sanders’ recent suggestion that Clinton has been “hugging” Obama in an effort to win over black voters. “I think that a lot of people resented that,” he said. “[Y]ou can’t use certain terminologies without people saying, ‘Well, wait a minute, now. They were working together through some tight stuff.’”

When I ask him whether Clinton “gets” race, he says, “I think she’s familiar with it. She worked for Marian Wright Edelman as he marched for Dr. King, and I think that her husband and his Arkansas background and living more with blacks, they were more ‘accultured.’ But comfort and culture is two different things.”

Truth be told, Sharpton gets a little yawn-inducing when he chats about this pair of basically acceptable liberals who have been diligent about paying their respects to him. Inevitably, the conversation swings back to Trump and a recent conversation he and Sharpton had after the GOP front-runner had watched the reverend’s describing as racist Trump’s comments about the Mexican government shipping America its rapists.

“He called me and said, ‘Why are you saying that?’” Sharpton told me. “I met with him, and I said … the birther stuff, the Mexican stuff is racist. [He said,] ‘You’re calling me a racist.’”

Sharpton shot back by telling Trump he’s never hit him with that label, but added, “That’s what you’re running on, and you’re getting endorsements from outright hate groups.” The exchange was tense, but respectful, he says.

Yet the very fact that Trump cared what Sharpton thought of him — coupled with the developer’s recently semi-softened rhetoric on health care (he’s vaguely promised to create a new system that would ensure nobody “dies on the street”) — is significant. And the reverend thinks Trump will ultimately ditch the wilder elements of his platform, just as he would say or do anything to get a building built or a Mike Tyson fight booked.

Trump, in Sharpton’s eyes, is “the kind of guy that adjusts and tries to deal with whatever he has to deal with, as he says, to make a deal. There’s no doubt in my mind, if he wins the nomination, that Trump will move to the center.”

