It’s easy to get an inflated sense of self when you’re running New York City, with an avid press corps chronicling your every utterance and the city’s global prominence providing a bully pulpit on topics from international terrorism to President Trump’s immigration policy.

That ego, however, has often been rapidly deflated when mayors decide — as they are wont to do — that they’d like to trade Gracie Mansion for the White House, a route littered with underwhelming poll numbers, underattended rallies and unceremonious exits long before a single vote is cast. Just ask Mayor Bill de Blasio.

Those potential pitfalls could also await the nascent candidacy of Michael R. Bloomberg, the former mayor who seemingly took the first step toward running for president on Friday, filing paperwork in Alabama to become a candidate in the Democratic primary in that state.

Mr. Bloomberg, however, comes to the 2020 campaign with an array of advantages that his failed predecessors did not have, including an enormous personal fortune, an experienced political infrastructure and a proven track record in corporate, philanthropic and policy worlds.

Yet, for all that, his only political experience is as New York City mayor. And that has been a very poor selling point for a series of contenders, including John V. Lindsay in 1972, Rudolph W. Giuliani in 2008, and most recently, Mr. de Blasio, who abandoned his 2020 dreams in September.

Still, the illusion persists, analysts say, because of the sheer size of the job and the arrogance and attitude that such a position can engender.

“Many mayors of New York City believe somehow that they are running their own country and the rest of the world should understand that,” said Hank Sheinkopf, a longtime Democratic political operative, adding: “Hubris is built into the job.”

“If they skin their knees, it’s a major story,” Mr. Sheinkopf said.

That trend line of failure for prominent New Yorkers has one notable outlier, of course: the current occupant of the Oval Office, Donald Trump, who was, until very recently, a proud New Yorker, albeit one who came to politics as a novice.

Timothy Naftali, a professor of public service at New York University’s Wagner School, said that Mr. Trump had disproved the notion that “a personality that’s successful in New York had a hard time developing a national following.”

Moreover, Mr. Naftali said that other mayors’ presidential runs each failed for unique reasons, including the poor national reputation of the city during Mr. Lindsay’s run and Mr. Giuliani’s inability to translate adoration in New York to a national audience.

“John Lindsay’s failure was not for the same reasons that Giuliani experienced failure,” he said, adding that while New York politicians tend to have deep and loyal defenders and surrogates inside the five boroughs, such provincialism often does not translate beyond the city limits.

“The secret sauce in New York mayoralty politics is not the same as the special sauce it takes to become president of the United States,” Mr. Naftali said.

Several political consultants said, however, that Mr. Bloomberg, 77, who served in City Hall from 2002 through 2013, was a special case: an outsider who had always bucked convention, including switching political parties and persuading the City Council to allow him a third term, despite term limits.

Sid Davidoff, a lobbyist and former aide to Mr. Lindsay, said that he believed that neither Mr. Lindsay nor Mr. de Blasio actually believed they could win the Democratic nomination — let alone the presidency — but “thought they should be in forefront of issues concerning urban areas.”

Mr. Bloomberg, he said, was a different case because of his wealth and broader, more prominent political portfolio since he left office on issues including public health, gun control and the environment.

“He has been in the forefront of issues of national interest,” Mr. Davidoff said. “And he’s in a much better position to really push that platform.”

Mr. Sheinkopf seconded this, saying that Mr. Bloomberg’s work since leaving office had only burnished his reputation, something he said would be amplified by money and all the political professionals that can buy.

“What’s different about this guy? He’s got $60 billion and a record,” he said, adding, “He’ll have the best people around him, and he’s loyal to his people.”

That said, no one who has served as New York City’s mayor has ever been elected president, a streak running back to DeWitt Clinton, who challenged James Madison in 1812 and lost after he could not win Pennsylvania.

Governors from New York have had slightly better luck, with four becoming president, though none has been elected since Franklin D. Roosevelt in 1932. Since then, others have tried and failed — Thomas E. Dewey in 1944 and 1948, Nelson A. Rockefeller in 1960 and George E. Pataki in 2016.

Still others have contemplated bids before deciding against it: Mario M. Cuomo’s vacillations were so well known that people called him Hamlet on the Hudson. More recently, Mario’s son, the current governor, Andrew M. Cuomo, has been mentioned as a possible candidate. Like his father, he has demurred.

For current New York politicians, the news of Mr. Bloomberg’s interest in the nation’s top job has been met with both skepticism and support.

Speaking at a conference in Puerto Rico, the New York attorney general, Letitia James, said she welcomed the former mayor into the race, praising his work on gun control and on women’s rights, though she wondered if his candidacy would hurt Joseph R. Biden Jr.’s chances.

As for why Mr. Bloomberg and other New Yorkers keep dreaming of Washington, Ms. James was certain of the answer.

“What is it about New York?” she said. “New York is the center of the universe.”

J. David Goodman contributed reporting from San Juan, P.R.

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