“I think he has challenges, but he has, I think, made a more-than-expected attempt to deal with the challenges,” Rev. Al Sharpton told POLITICO, noting endorsements like Columbia, S.C. Mayor Steve Benjamin and other black leaders who were early endorsers. “I don’t know how much it will work, but I can say he’s put more of an effort in it than I would have thought.”

Bloomberg flew here to attend Sunday services at Vernon Chapel AME Church before delivering the most sweeping and anticipated address of his young campaign: A plan to increase job opportunities and home ownership in black neighborhoods and invest $70 billion in struggling areas across the country.

His pitch, which takes its name from the Greenwood section of Tulsa known as “Black Wall Street” that was destroyed in the race massacre of 1921, was designed to tackle the systemic bias keeping many African Americans from advancement—as he put to parishioners at the church — “righting what I think are historic wrongs and creating opportunity and wealth in black communities.”

Michael Bloomberg greets the Rev. Robert Turner during a service at the Vernon AME Church in Tulsa, Okla., on Sunday. | Sue Ogrocki/AP Photo

Bloomberg’s strategy of skipping the first four voting states — underwritten by his vast fortune — has given him a wide-open playing field in areas with large black populations to try to define himself to voters, many of whom have stuck with former Vice President Joe Biden. In the speech Sunday, the billionaire who made his fortune on New York’s Wall Street went even further to acknowledge his white privilege.

“As someone who has been very lucky in life, I often say my story would only have been possible in America — and I think that’s true,” Bloomberg said, as hundreds filled the Greenwood hall and spilled into an overflow room. “But I also know that my story might have turned out very differently if I had been black, and that more black Americans of

my generation would have ended up with far more wealth, had they been white.”

“Instead,” he said, “they’ve had to struggle to overcome great odds, because their families started out further behind, and excluded from opportunities — in housing, in employment, education, and other areas.”

Bloomberg’s plan calls for one million new black homeowners and 100,000 new black-owned businesses in the next decade. Banks would need to update their credit-scoring requirements while he’d also create a Housing Fairness Commission funded with an initial $10 billion.

Organizationally, the event was a show of force for Bloomberg in a red state where Democratic activists and supporters said they’ve been starved to have in someone who could take on Donald Trump. Several prominent black political and business leaders were on hand from across the country, with Chicago heavyweight John Rogers Jr. introducing the former mayor and telling POLITICO that he’s made his endorsement: “I’m with him all the way,” Rogers said.

“This is a first down. It’s a good play. It wasn’t a touchdown, but he’s moved the ball down the field,” said Jarrod Loadholt, an Atlanta-based Democratic consultant. “Democrats writ large don’t speak meaningfully to economic opportunity when it comes to communities of color,” he added, contending that candidates tend to focus primarily on “safety net issues.”

But the degree to which stop and frisk has dominated negative assessments of Bloomberg has only magnified the issue as his Achilles heel in the Democratic primary. Mark Thompson, a veteran radio host and NAACP activist, dismissed Bloomberg’s recent attempts in recent weeks to move beyond the issue as an “utter misreading of the room,” given the party’s progressive streak.

“You can’t say ‘I’m sorry’ in 2020 when you haven't said ‘I’m sorry’ over the past decade,” Thompson said. That would split the Democratic coalition. Even progressive whites would not keep their progressive bonafides.”

Sharpton and others vociferously criticized his criminal justice record when he was mayor, including stop and frisk policing and his stance on five teenagers wrongly convicted of raping a woman in Central Park — now the subject of a documentary that underscores how the law enforcement system impacts young black and Latino men.

“You can’t say ‘I’m sorry’ in 2020 when you haven't said ‘I’m sorry’ over the past decade." Mark Thompson, a veteran radio host and NAACP activist

The Central Park rape took place before Bloomberg was elected to office. His administration fought a civil lawsuit alleging racial discrimination and he defended the police, though he did not disagree with the decision to vacate the convictions. Shortly after announcing his presidential campaign he was asked about the case and replied, “I've been away from it for so long, I just really can't respond because I just don't remember.”

“Mike Bloomberg has baggage — stop and frisk and the Central Park Five," Sharpton said. "But Joe Biden has the crime bill and Bernie Sanders voted for it.”

Maya Wiley, who once chaired the Civilian Complaint Review Board in New York City, was circumspect about Bloomberg’s apology for stop and frisk, given his insistence the practice was necessary to drive down crime during his dozen years in office. He’s been forced to answer questions about it in nearly every big national TV interview he’s done of late.

While Bloomberg is responsible for reversing course, under extensive political and legal pressure, he never publicly acknowledged the change, allowing his successor and chief critic, Bill de Blasio, to exaggerate his own role in the reform.

“He obviously had to apologize. He has not done it well enough to win over the black vote, certainly not the black vote in New York, who has experienced firsthand what stop and frisk meant, and how harassing, humiliating and abusive it was with very little need or impact on crime,” Wiley, who previously served as de Blasio’s City Hall attorney, said.

“He doesn’t really understand just what black people are concerned about in enough of a personal way to be relatable,” she added about Bloomberg. “And I say that not because I don’t think he is trying, but because I don’t think he understands.”

In his Tulsa speech, Bloomberg again expressed regret for using stop and frisk in his determination to halt gun violence. “As I have said, I was wrong not to act faster and sooner to cut the stops and I’ve apologized to New Yorkers for that — for not better understanding the impact it was having on black and Latino communities.”

Bloomberg also took pains to draw on the experiences of black Americans, using the massacre to illustrate centuries of injustice: More than 6,000 were arrested during and after the brutal episode — all of them black, while no white people went to jail. While it was one of the most painful sagas in American history, Bloomberg admitted he’d never heard of it until traveling to Tulsa recently to help underscore the point that so many mass killings of African Americans between 1917 and 1923 were never taught in high schools and colleges.

He tells the story of his father donating to the NAACP, telling a young Bloomberg that “discrimination against anyone is a threat to everyone.”

“I didn’t know it at the time, but when my parents moved to the house I grew up in, the owners wouldn’t sell to them,” he said. “They didn’t want a Jewish family in the neighborhood. Luckily for us, our Irish lawyer was willing to buy it and transfer it to my parents. But if my mother and father had been black, we would not have been so lucky. And we would not have grown up in that neighborhood.”

Bloomberg’s courtship of black voters comes as Biden holds onto a commanding and seemingly unshakable lead among them. A Washington Post-Ipsos poll conducted earlier this month found Biden the clear frontrunner, at 48 percent. That’s more than double Bernie Sanders’ 20 percent. Bloomberg stood at just 4 percent. Particularly problematic for Bloomberg was his negative rating among respondents: When asked whom they would not consider for the nomination, he came in second to long-shot contender Tulsi Gabbard.

Loadholt said he remains skeptical Bloomberg could move the needle enough to compete in the primary. “There are some voters — African Americans — who will like Michael Bloomberg,” he said. “But does this get him to 15% in Alabama, where he can get some delegates?”

Bloomberg is grounding his broader appeal in anti-Trump fervor and arguments about his potential electability in November — both areas where Biden has so far excelled with black voters. Still, Bloomberg’s spending, now upward of $250 million alone on advertising, has helped him rise modestly with voters overall in national polls and created a dynamic that’s hard to ignore, said Adrianne Shropshire, the executive director of BlackPAC.

With such a massive premium on winning, voters could be swayed by a candidate that’s able to use Trump-like tactics to defeat him.

“Part of the reason why there is that support for Biden is he’s the ‘scrapper from Scranton,” Shropshire said. “Bloomberg is a New Yorker, too. Bloomberg knows how to use those New York City machine politics as well. And there is some sense he can defeat Trump because he understands what New York in the street politics is about — and, because he has the money.”

