President Trump and former Gov. Andrew M. Cuomo are arguably two of the most notable characters in New York City’s recent history, and their personal and professional lives have been intertwined for decades.

Born and raised in Queens, the two men have followed paths that help explain the city, its unique style of politics and the close ties between the real estate world, where Mr. Trump made his name, and government, through which Mr. Cuomo charted his rise.

The New York Times reported this week that Mr. Trump had taken a keen interest in his hometown’s mayoral race and had recently spoken to Mr. Cuomo about the contest. The former governor, who lost the Democratic mayoral primary to Assemblyman Zohran K. Mamdani, is running in the general election as an independent.

It’s not known what exactly Mr. Trump said to Mr. Cuomo, or who initiated the call. Mr. Cuomo said on Thursday that he couldn’t recall the last time he had spoken to Mr. Trump, later adding that he had not talked to the president “about the mayor’s race.”

But Mr. Trump has said publicly that Mr. Mamdani’s election would be a disaster for the city and that Mr. Cuomo should remain in the race.

The relationship between the two New Yorkers — which Mr. Cuomo jokingly characterized at one point as a “dysfunctional marriage” — has had many ups and downs. Here is a look at seven of them.

Two politically connected ‘Queens boys’

After emigrating from Sicily, Mr. Cuomo’s grandfather, Andrea Cuomo, opened a grocery store in Jamaica, Queens.

The store soon drew a regular patron, Fred Trump, a politically connected developer building homes nearby.

Mr. Cuomo’s father, Mario Cuomo, who would later serve as governor, often sat in the back as his parents worked. Soon after graduating from law school, he joined a firm that represented Fred Trump. Wayne Barrett, an investigative journalist who covered Mr. Trump’s ties to the Cuomo family closely for decades, recounted how the elder Mr. Cuomo would head to “Fred Trump’s headquarters on Avenue Z for business lunches at which Trump dished out the cheese sandwiches himself.”

Growing up in their fathers’ world, the younger Mr. Cuomo and Mr. Trump learned a particular method of transactional politics, which they practice to this day. Speaking about Mr. Trump in a podcast interview in March, Mr. Cuomo said that they were both “Queens boys” and that the president “knows the situation in New York City. It is his hometown. I think that he wants New York City to appreciate him.”

Cuomo the lawyer and Trump the client

After working on several of his father’s campaigns and then as an official adviser, Andrew Cuomo left government work and joined a law firm run by close associates of his father.

One of the firm’s clients was Donald Trump. Understanding the role politicians play in getting things built in New York City, Mr. Trump had donated to Mario Cuomo’s campaigns. Mr. Barrett reported that by the end of the 1980s, the developer was the elder Mr. Cuomo’s largest corporate donor.

Andrew Cuomo always said it was the “cheapest shot you can take at me” when people criticized him for his law work. But when he started a homelessness nonprofit, Mr. Trump donated $10,000.

Two Page Six regulars

The gossip pages of New York’s tabloids detailed the exploits of Mr. Trump and Mr. Cuomo. The men ran in similar social circles, and Mr. Barrett reported that Mr. Trump attended Mr. Cuomo’s birthday party in 1989. They spent 30 minutes in a corner talking.

The Times also reported about an encounter between Mr. Cuomo and Mr. Trump, where the future president beckoned the future governor to his limousine, saying he had “something incredible” to show him.

Inside the vehicle was Marla Maples, who would later, in 1993, become Mr. Trump’s second wife.

In 1990, Mr. Cuomo was about to marry Kerry Kennedy just as Mr. Trump was on the way to divorcing his first wife, Ivana. Mr. Cuomo’s bachelor party took place at a Manhattan bar, and Mr. Trump recorded a video testimonial.

“Whatever you do, Andrew,” Mr. Trump told the groom-to-be, “don’t ever, ever fool around.”

Sparring partners

One of the first big fights between Mr. Cuomo and Mr. Trump came in the mid-1990s. Mr. Trump was trying to develop a stretch of Manhattan’s Upper West Side, and he was seeking federal help from Mr. Cuomo, who was serving as President Bill Clinton’s secretary of Housing and Urban Development.

Mr. Trump called Mario Cuomo, then the former governor, hoping for help getting to his son. When the elder Mr. Cuomo balked, Mr. Trump snapped.

“For years I’ve helped you and never asked for a thing, and when I finally need something, and a totally proper thing at that, you aren’t there for me. You’re no good,” Mr. Trump recalls saying.

This anecdote was recounted in “How to Get Rich,” one of Mr. Trump’s books, in a chapter titled, “Sometimes You Have to Hold a Grudge.” But by the early and mid-aughts Mr. Trump had become a prolific donor to the younger Mr. Cuomo’s political campaigns for attorney general and governor of New York.

Flirting with an electoral face-off

In 2013, a band of Republicans tried to persuade Mr. Trump to challenge Andrew Cuomo in the 2014 governor’s race.

Mr. Trump was told by advisers that he could run against Mr. Cuomo and use it as a springboard to run for president. As he considered the move, Mr. Trump traveled around the state, meeting with numerous New York Republicans. He ultimately did not run.

When Mr. Trump did run for president in 2016, Mr. Cuomo instead campaigned aggressively for former Secretary of State Hillary Clinton, who previously served as a Democratic senator of New York. The tough election did not appear to mar their relationship.

“We get along very well,” Mr. Trump said that year.

A pandemic falling-out

The two sons of Queens were at the peak of their fame during the first months of the Covid pandemic. As Americans huddled in their homes fearing for their lives, televised updates by Mr. Cuomo, them the New York governor, and Mr. Trump, then the president, formed a potent split screen.

For many, Mr. Cuomo’s appearances were a balm to the chaos and misinformation that emanated from Mr. Trump — won Mr. Cuomo an Emmy Award and elevated him as one of Mr. Trump’s main foils.

Mr. Trump “says a lot of things, right? They’re not necessarily facts, they’re not necessarily true,” Mr. Cuomo said of Mr. Trump at a press briefing in Albany in July 2020. “He wants to deny the Covid virus. He has from Day 1.”

Fund-raising off a resignation

Mr. Cuomo resigned as governor of New York in 2021, amid growing anger over his handling of Covid-19 deaths in nursing homes and a slew of sexual harassment allegations, which he denied.

Cuomo “is a TOTAL LOSER, and New York, as well as the entire Country, is better off without him,” Mr. Trump wrote in a fund-raising pitch shortly after the resignation.

As he campaigned for New York City mayor this year, Mr. Cuomo was seemingly caught between bashing his longtime sparring partner and saying that their relationship would be a boon for the city, if he were to become mayor.

“I know him very well. We’ve had intimate dealings for many years,” he said in a podcast interview in April.

In the same appearance though, Mr. Cuomo said, “you have to be willing to stand up to Donald Trump.”

Publicly, Mr. Cuomo has taken a tougher stance recently against the president. He has said the White House is working to “undermine our democracy,” and he has criticized Mr. Trump’s immigration policies.

But this week he told business leaders privately, “I know, personally, he doesn’t want to fight with me.”

He added, “Personally, I don’t want to fight with him, right? So I don’t think he’s going to be eager to create a conflict with us.”