Anthony Weiner (R) greets a man while courting voters outside a Harlem subway station a day after announcing he will enter the New York mayoral race on May 23, 2013 in New York City. Weiner is joining the Democratic race to succeed three-term Mayor Michael Bloomberg after he was forced to resign from Congress in 2011 following the revelation of sexually explicit online behavior. (Photo by Mario Tama/Getty Images)

The morning after announcing his run for mayor via video, Anthony Weiner’s very first campaign stop was in Harlem, shaking hands with commuters at a subway stop on the corner of 125th Street and Lenox Avenue.  Weiner’s choice of kickoff location reveals a great deal about New York’s minefield of racial and ethnic politics – and serves as a reminder of Weiner’s past missteps.

The crush of reporters who swarmed around Weiner focused, almost without exception, on the juicy story of how Weiner resigned from Congress in disgrace two years ago, shortly after a conservative website exposed his odd habit of sending raunchy messages and photos to women he’d met online.

It’s an undeniably fascinating storyline, and it’s unclear whether New Yorkers are ready to forgive Weiner and accept him as a candidate for mayor. A recent poll suggests half of city voters don’t think he should even bother to run, but the 8.3 million denizens of the Big Apple are famously tolerant of strange behavior and oddball characters; the sheer density of the place demands a live-and-let-live attitude.

Money is only part of the battle

In a Democratic primary that will likely draw only 700,000 voters, my guess is that Weiner will get a fair hearing  and mount a plausible effort.  His campaign has more than $4 million in funds left over from the days before he quit Congress, and could receive more than $1 million in matching funds.

But money is only part of the battle.  Weiner is running in city that is now mostly non-white. Bruce Gyory, a top political consultant, estimates that black, Latino and Asian New Yorkers will cast more than 58 percent of the Democratic primary vote in September, meaning any white candidate who hopes to win must make inroads in those communities.

That won’t be easy.  Weiner is battling candidates for mayor that include Taiwan-born John Liu, the city comptroller and Bill Thompson, the black former comptroller who nearly beat incumbent mayor Mike Bloomberg four years ago, winning 80 percent of the black vote and 65 percent of Latinos.

Liu and Thompson remain solidly anchored in those communities, and another contender, Bill de Blasio, is white but married to a dynamic, high-profile African-American woman.

Bottom line: it will take more than a visit to Harlem for Weiner to pull a significant portion of the black vote.

“The Jesse Jackson incident”

And then there’s Weiner’s “Jesse Jackson” incident from long ago, little-known to most journalists but still a source of grumbling among older political operatives.

Back in 1991, during Weiner’s first bid for political office – a successful effort that made him the youngest member of the New York City Council – his victory was marred by a controversial, anonymously distributed and racially-tinged political ad.

The time was just weeks after an explosive race riot in the Crown Heights section of Brooklyn had led to fierce criticism of David Dinkins, the city’s first black mayor.  Weiner, a 27-year-old political aide, was locked in a tough race against two better-known rivals, one of whom, Adele Cohen, was backed by a coalition of liberals and unions.

Weiner distributed 10,000 flyers warning voters not to support Cohen, who was tagged as part of a “David Dinkins/Jesse Jackson Coalition.”

It was an unfair smear, appealing to the worst fears of a mostly-Jewish district, and the flyers went out so close to election day that Cohen had no chance to respond. (And, for what it’s worth, she had never met Jesse Jackson and was not a close ally of Dinkins.)

Weiner won in a squeaker, finishing 195 votes ahead of Cohen.  He immediately apologized for the dirty trick, sending a note to Cohen that said, in part: “I made a mistake that cannot be undone. I’ll have to live with it. I’m sorry you do as well. I hope that in time I will have the opportunity to redeem myself to you and to the many others who are rightly angry with me.”

That wasn’t good enough for the New York Times, which blasted the young councilman in an editorial, titled “Smears and Fears,” for “hit and run tactics” and “coarse appeal to racial fears in his mostly white district.”

Trying to make up for a mistake

More than 20 years later, Weiner remains sorry. “I sent a mailer in an election 22 years ago that I should not have. I apologized at the time and have worked very hard my entire life to fight for issues that bring people together,” he told the New York Post.

Weiner went on to rise from the City Council to Congress. Cohen has never forgiven him. “I don’t think a person of his character should be mayor,” she told the Post.

In 2005, Weiner – perhaps mindful of the 1991 furor – dropped out of a contentious race for mayor rather than press for a recount and possible runoff against Fernando Ferrer, a more senior Puerto Rican Democrat who went on to lose to Mike Bloomberg.

Weiner’s dropping out was seen as an act of political statesmanship that would create goodwill among Latino power brokers if and when he made another run.  He will no doubt try to call in that favor this fall.

In 2006, Weiner deftly executed a similar maneuver, endorsing a Jamaican-American candidate, Yvette Clarke, over a Jewish rival in a tough congressional race. That didn’t erase the 1991 debacle, but it won Weiner some black allies. He built on the effort by hiring a talented black political consultant, Camille Joseph, as a senior campaign aide.

Weiner re-emerges from his two years in the political wilderness with some signs of rust. Local media noted that his campaign website features a skyline of Pittsburgh, not New York, and one of his staunchest backers from 2005, the firefighters union, says they won’t even consider backing him again.

And most important, in a city where all politics is tribal, Weiner must try to deepen his ties to a skeptical black electorate.