Senate Minority Leader Charles E. Schumer D-N.Y.) delivers remarks at President-elect Trump’s inauguration ceremony. (Alex Wong/Getty Images)

Donald Trump always had a soft spot for his fellow outer-borough kid who made it big. He recalls giving Chuck Schumer $500 when the young state legislator from Brooklyn first ran for Congress — the first of several donations. Trump attended a fundraiser for Schumer thrown by hip-hop mogul Russell Simmons. And Trump entertained Schumer at parties and fundraisers in Trump Tower and at his Mar-a-Lago estate in Florida.

Trump and Schumer were never pals, but they got along fine, two power players who had never quite been accepted in the inner circle of their chosen fields, two sharp-elbowed guys who led with their mouths and won power in part by mastering the art of being in the news.

Now, as Trump enters a pivotal passage in his new presidency, champing for a big win ahead of the 2018 congressional campaign, people in both parties thought the relationship between Trump and Schumer, the Senate minority leader, might provide a path out of Washington’s political paralysis. But on Tuesday, when Schumer and House Minority Leader Nancy Pelosi (D-Calif.) pulled out of a scheduled meeting at the White House, the limits of that relationship became palpably evident. And the chances for a deal ahead of a Dec. 8 spending deadline grew that much smaller.

Schumer said he's still open to negotiating with Republicans in Congress, but any quick New Yorker-to-New Yorker agreement to avert a government shutdown and resolve the status of the "dreamers," about 600,000 young undocumented immigrants who were brought to the United States as children, appeared to be stillborn. Schumer and Trump traded snippy remarks late Tuesday. The senator called the president "a destructive force." Trump, sitting between empty chairs set behind Schumer's and Pelosi's nameplates, accused the two of being "weak on military" and "all talk . . . no action."

The connection between Schumer and Trump has already been among the most volatile, promising and surprising of many mercurial relationships in the short history of the Trump administration. On the morning after this month's terrorist attack on Manhattan's West Side, Trump tweeted a shot at Schumer, calling the diversity visa lottery under which the accused terrorist entered the United States "a Chuck Schumer beauty."

Whereupon Schumer opined that "I guess it's not too soon to politicize a tragedy." Following which Trump's spokesman, Sarah Huckabee Sanders, said the president didn't intend to blame Schumer for the attack.

The sniping continued Tuesday, when the president tweeted that “ ‘Chuck and Nancy’ . . .want illegal immigrants flooding into our Country unchecked, are weak on Crime and want to substantially RAISE Taxes. I don’t see a deal!”

That prompted Schumer and Pelosi to cancel the meeting with Trump and Republican leaders. But congressional Republicans, who grumble privately about Trump’s frequent attacks on his own party, believe Trump may yet find occasional alignment with Schumer and the Democrats — on infrastructure, illegal immigration or spending.

“If we’re going to get results, it’s going to be from those two,” said Rep. Peter T. King (R-N.Y.), a Long Islander who says Trump makes deals best when he’s at ease with those on the other side. “Trump has no patience for all that polite circumlocution of Washington. He didn’t realize how much he really is a New Yorker till he was away from the city for a few months. With Schumer, he can be a wiseguy. They interrupt each other, finish each other’s sentences. The president feels comfortable.”

Schumer has clearly been on the president’s mind. At a meeting with six members of Congress just before his trip to Asia a few weeks ago, Trump kept bringing up Schumer’s name, even though the senator was not present. “He raised Schumer’s name often, in a very personal, very playful way,” said a Senate source familiar with the meeting. “He’d talk about something he was going to do with China, and he’d say, ‘Chuck’s not going to be happy about that.’ ”

Schumer boasted to a Senate colleague, in a conversation caught by a C-SPAN microphone earlier this fall, that Trump “likes us. He likes me, anyway. . . . Oh, it’s going to work out.”

But that same morning, Trump had tweeted that "no deal was made" with Schumer and Pelosi to let the dreamers stay in the country.

President Trump meets with congressional leadership in the Oval Office on Sept. 6. Trump sided with Democrats in the meeting on a plan to fund the government for a three-month stopgap. (Bill O'Leary/The Washington Post)

Is a jocular, comfortable vibe enough to forge deals across party lines?

“Neither the president’s attempts to flatter nor his name-calling have an effect on the relationship,” said Matt House, a spokesman for Schumer, who declined to be interviewed for this article. “What drives the relationship and ultimately leads to agreements or conflict is the president’s policy proposals,” House said.

If Trump proposes ideas that “don’t violate Democrats’ values and principles,” Schumer will work with him, the spokesman said. But “if the president continues to pursue an agenda that takes us backwards, Senator Schumer will hold the line.”

Barbs and blame are routine in the Trump-Schumer relationship, not because they are political enemies — after all, Trump was a Democrat for much of his career as a brash Manhattan developer — but because of where they’re from and how they operate.

One of the roughest parts of the president’s transition from Trump Tower to the White House has been finding his new posse. A man of deeply ingrained habit, Trump, despite his TV-polished reputation for firing people, kept the same tight circle of advisers for decades. Many of those were fellow New Yorkers.

The president, who often grates against the stilted manners and glacial pace of Washington, visibly loosens in the presence of fellow New Yorkers, especially outer-borough and Long Island guys such as Fox News host Sean Hannity or erstwhile White House communications director Anthony Scaramucci, according to people who have watched such encounters.

When Trump met with congressional Republicans in the spring about health care, he told Rep. Mark Meadows (R-N.C.) that if he didn’t support Trump’s plan, “I’m going to come after you.”

“A lot of Republicans grumbled about that,” King said, “and the president said, ‘Hey, I’m kidding around.’ Those guys just don’t get that kind of language. But that’s how we are. When he’s talking to Chuck, he doesn’t have to worry about that. They both just want to get the goddamn thing done.”

Trump knows he can slam Schumer as “head clown” or “Crying Chuck” and the senator will keep talking to him. In a 40-minute meeting Trump held with at least eight officials from New York and New Jersey last month to talk about transportation projects, Schumer and Trump dominated the conversation and Trump kept reaching across economic adviser Gary Cohn to shake Schumer’s hand, according to a participant in the meeting.

Schumer talks to Trump in the Oval Office on Sept. 6. (Alex Wong/Getty Images)

Schumer and Trump share a classic outer-borough combination of tough talk and sensitivity about not being taken quite as seriously as the fancy guys from Manhattan. Both of them spend many hours on the phone, schmoozing friends and foes alike.

They also share an approach to humor that can land with a thud in Washington. At their dinner in September, the president could joshingly invite Schumer to “have some meatballs — they’re kosher,” without fear that he’d take offense, according to a guest who witnessed the exchange.

“In the old World War II movies, there was always some numbskull from Brooklyn, the straight-talking lug who everybody loved because you always knew where you stood with him,” said Jim Kessler, a former Schumer senior staffer who now works at Third Way, a policy nonprofit. “Trump and Schumer talk like that. Trump can feel like he speaks a foreign language to a lot of Americans, but New Yorkers know that language of insults.”

But two people can share a sense of which barbs are just jests and still be quite different.

“Trump is red carpet, and Chuck is the Sheepshead Bay co-op annual meeting,” Kessler said. “Trump is fine china, and Chuck is Chinese takeout. Trump’s dad was a millionaire; Chuck’s dad was an exterminator.”

Inside the White House, many advisers remain wary of working with Schumer. When Schumer and Pelosi emerged from a Blue Room dinner with Trump in September and announced that they had a deal to permit the dreamers to stay in the country, they went further than what Trump had accepted, a White House official said.

“There was a lot of warmth and feeling in the dinner,” the official said, but “Schumer and Pelosi were under such pressure to produce something that they got ahead of themselves.” Yet White House budget director Mick Mulvaney emerged from the dinner confirming that “we have the makings of a deal” with Schumer and Pelosi.

Both sides in the relationship portray the other as being captive to his base. Schumer’s camp argues that the president, left to his own devices, would hew closer to the moderate Democratic leanings he expressed most of his life. Under pressure to cater to the Republicans who put him in office, they say, he reverts to a hard line on immigration and security issues.

Trump aides, however, say it’s Schumer who can’t be flexible because his base is dead set against cooperating with the president. Even before Trump took office, protesters gathered outside Schumer’s Brooklyn home with signs that said, “Make Us Proud or We’ll Primary You. Don’t Cut Deals With the Devil.”

“They have a good rapport, but it’s a complicated relationship,” said Marc Short, the White House legislative affairs director. “If you look at confirmation of our appointments, Schumer has been as obstructionist as possible. It’s absurd. We haven’t see a lot of cooperation.”

Schumer, 67, and Trump, 71, grew up in the same New York political arena. Trump’s developer father took his teenage son with him to neighborhood Democratic clubs in Brooklyn on weekends, visiting local party chieftains whose help he might someday need. Schumer’s mother volunteered in her neighborhood and pressed her son to succeed by studying hard.

Schumer speaks to Capitol Hill journalists June 22 about the Senate’s attempt to repeal the Affordable Care Act. (Melina Mara/The Washington Post)

Schumer’s path took him from valedictorian at his public high school to a perfect 1600 on his SAT and on to Harvard and Harvard Law. He joined Sen. Eugene McCarthy’s (Minn.) 1968 campaign for the Democratic presidential nomination and soon made his own run for a state Assembly seat. Trump, never the studious type, was already devoting much of his time to the family business while he was in college.

Once Trump broke off on his own to build hotels and office towers in Manhattan, he needed political cover, just as his father had. Even in his 20s, Trump cultivated politicians, held fundraisers and invited officeholders to his many news conferences.

When Republican Tom Kean was governor of New Jersey in the 1980s, he would run into Schumer at Trump’s big parties. “Trump would make sure the rich and powerful were there, as well as the politicians he might need to get permits for his next project,” Kean said. “He and Schumer both liked to know everybody.”

Trump even put Schumer up as a prize on his TV reality show, “The Apprentice.” In 2006, contestants on the show vied for an awards package including a meeting with the senator.

Between 1996 and 2010 — when Schumer’s career was blossoming and Trump was variously a Democrat, a Republican and an independent — Trump donated $9,000 to Schumer.

They came head to head on New York issues only rarely. In 2007, they were on opposing sides of a conflict over Starrett City, the country’s largest subsidized housing complex, with nearly 6,000 apartments in 46 buildings near Jamaica Bay in Brooklyn.

Schumer sided with tenants who feared that the sale of their homes might mean huge rent hikes or even eviction. Trump, whose father had been a major investor in the complex in the 1970s, still owned about 4 percent of the property and was pleased to cash out.

Trump shakes hands with Schumer as he signs his Cabinet nominations into law at the Capitol on Jan. 20. (J. Scott Applewhite/Associated Press)

Schumer called the decision to sell disgraceful and accused the owners of trying to “maximize every nickel they can get at the expense of the tenants.”

Trump’s retort: “You can’t stop free enterprise. This is not Communist China.”

But the two men stayed on the fringes of the issue. The complex is now in the process of being sold, a deal that could produce a $14 million payoff to Trump.

In 2014, Trump and Schumer found themselves on the same side of an effort to keep the Buffalo Bills in New York. Schumer was deeply involved for months, calling owners, scouting ways to ensure that the franchise remained in Buffalo, one of the league’s smaller, more frigid cities. Trump, who put himself forward as a possible owner of the team, “never seriously pursued it,” according to a source close to Schumer.

Trump likes to do business with people who, as he sees it, can take a punch. “That’s who he is,” said the Rev. Al Sharpton, who has crossed swords with Trump and occasionally found common cause with him. “He comes from construction workers and builders, that Queens blue-collar, white-ethnic world. He built himself into a New York personality, an environment where Page Six and the tabloids mean something to him.”

Sharpton argues that Trump’s affinity for fellow outer-borough guys — and they are nearly always men — “comes out of a place with a certain racial dynamic and attitudes that are different from the rest of the country.” Trump “learned politics watching [former New York mayors] Ed Koch and Rudy Giuliani, whereas he looks at a McConnell or Ryan and he just doesn’t get that.”

The feeling may be mutual. Soon after Trump took office, McConnell emerged from a White House meeting and allowed that “I enjoyed the president and Sen. Schumer talking about all the people they knew in New York.”

Despite their common New York DNA, the president and a leader of the party that defines itself as the resistance to Trump may not be able to bridge the gulf between them.

“Trump’s dealt all of his career with the kind of bleeding liberals that Chuck represents, the union bosses he needed to get his buildings built,” Sharpton said. “But for them to make any deals, Schumer’s got to come out of the room with something to take back to Brooklyn, and Donald Trump’s got to take something back to the 21 Club. Right now, they’re in such different places that it could just end with a series of stalemates.”