A newborn Trump-Dem fellowship? It’s complicated.

President Trump and Senate Minority Leader Charles Schumer Chuck SchumerVideo of Lindsey Graham arguing against nominating a Supreme Court justice in an election year goes viral Graham signals support for confirming a Supreme Court nominee this year Pelosi orders Capitol flags at half-staff to honor Ginsburg MORE (D), two New Yorkers with a long and checkered history, joined forces this week on a high-stakes fiscal bargain that shoved aside the wishes of Trump’s Republican allies.

The two party leaders — both Big Apple power-brokers known as sharp-elbowed dealmakers — have sparred throughout the year, trading shots over a host of issues.

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But in a move that stunned Washington, the pair, joined by House Minority Leader Nancy Pelosi (D-Calif.), united on Wednesday to secure a short-term deal to fund the government, raise the debt ceiling and provide aid to the victims of Hurricane Harvey — a proposal initially opposed by Senate Majority Leader Mitch McConnell Addison (Mitch) Mitchell McConnellMomentum growing among Republicans for Supreme Court vote before Election Day Trump expects to nominate woman to replace Ginsburg next week Video of Lindsey Graham arguing against nominating a Supreme Court justice in an election year goes viral MORE (R-Ky.) and House Speaker Paul Ryan Paul Davis RyanKenosha will be a good bellwether in 2020 At indoor rally, Pence says election runs through Wisconsin Juan Williams: Breaking down the debates MORE (R-Wis.).

Trump and Schumer built on the nascent alliance by agreeing to seek reforms that would altogether eliminate the need for Congress to hike the debt ceiling — yet another proposal opposed by the president’s Republican allies.

And on Thursday evening, the pair met again as part of a larger group of New Jersey and New York lawmakers gathered at the White House to discuss funding for the Gateway Program, a multibillion-dollar proposal to tunnel a rail line beneath the Hudson River.

Rep. Pete King (R-N.Y.), who attended the White House meeting, said there was “very good chemistry” between Schumer and the president, predicting this week’s negotiations are a sign that Trump, after largely ignoring or insulting the Democrats for months, is ready to start reaching across the aisle for the sake of winning legislative victories.

“For me, it goes beyond that particular deal. It’s the president sending a message that he’s going to work across the aisle to get things done. He’s not going to allow any small factions to dominate the Congress,” King told The Hill. “Reagan did it with Tip O’Neil; Eisenhower did it with LBJ. I mean, that’s government.”

Yet the hot-and-cold relationship between the president and top Democrats leaves plenty of open questions about how well they’ll work together moving forward.

Trump’s relationship with Schumer stretches back decades, to the mid-1990s, when the Manhattan billionaire first started funneling money to Schumer’s campaigns — donations that have totaled thousands of dollars over the years. Trump’s campaign largess has benefited Pelosi, as well. In the 2006 cycle along, Trump donated $20,000 to the Democratic Congressional Campaign Committee, helping the Democrats win control of the House that year — and making Pelosi the first female Speaker in the country’s history.

After his election in November, Trump praised Schumer’s intellect — “he is far smarter than Harry [Reid],” Trump tweeted — and his “ability to get things done.”

“I have always had a good relationship with Chuck Schumer Chuck SchumerVideo of Lindsey Graham arguing against nominating a Supreme Court justice in an election year goes viral Graham signals support for confirming a Supreme Court nominee this year Pelosi orders Capitol flags at half-staff to honor Ginsburg MORE,” Trump said.

But relations quickly soured after Schumer, newly tapped as Democratic leader, began attacking Trump’s plans to repeal ObamaCare. In a notable tweet, the president characterized Schumer as the Democrats’ “head clown.”

But in the rough-and-tumble world of New York politics, such attacks are simply a routine part of negotiations, according to area lawmakers.

“We can brush off insults in ways that aren’t personalized, and I think it’s clear that Schumer and Trump were able to do that,” said Rep. Hakeem Jeffries (D-N.Y.), who represents parts of Brooklyn. “Both of them have been hard on each other, but were able to come together and reach an agreement and that is a typical thing that happens in New York: hardball tactics in negotiation still yield an agreement.

“[We] don’t take it personally,” he said.

King, who represents parts of Long Island, agreed.

“Being from New York, neither one of them takes that stuff seriously,” he said.

Pelosi also praised the Big Apple connection; Schumer, she said, “could speak New York to the president.”

Yet Pelosi also sounded a cautionary tone, saying that while she hopes to work with Trump on immigration, tax reform and infrastructure, Democrats won’t sacrifice their ideals to do so. She warned, in particular, that the Democrats will oppose any tax-reform proposal that showers heavy benefits on the wealthy.

“[We’re] always hopeful that we can find common ground, which we have a responsibility to do,” she said. “If we can't find it, we stand our ground.”

There are risks for Democrats cutting a deal with Trump, a mercurial president largely despised by the Democrats’ liberal base.

“Our base is so riled up about Trump that any agreement of any kind, like this, will have to be very carefully presented [to constituents], because it’s not that they want dysfunction, but they have zero trust of this president,” said Rep. Gerry Connolly Gerald (Gerry) Edward ConnollyJudge issues nationwide injunction against Postal Service changes House panel advances bill to ban Postal Service leaders from holding political positions Shakespeare Theatre Company goes virtual for 'Will on the Hill...or Won't They?' MORE (D-Va.).

With that in mind, a number of lawmakers are already skeptical that the fiscal agreement heralds a new era of bipartisanship.

“The president is completely transactional. He’s not wed to them, he’s not wed to us, he’s wed to himself and whatever his agenda dictates at the time,” said Rep. John Larson (D-Conn.), who was quick to note that Trump and the Republicans simply didn’t have the votes to pass the debt-limit proposal on their own.

“If he did, do you think he’d be talking to us?” Larson asked.

Ryan and McConnell both downplayed Trump’s deal with the Democrats, arguing the president wasn’t bucking the Republicans so much as he was seeking to demonstrate bipartisan cooperation in the aftermath of Hurricane Harvey and facing the threat of Hurricane Irma.

“The president made it really clear, and what he was aiming for in that meeting yesterday was a bipartisan moment, while the country is facing two horrible hurricanes,” Ryan said Thursday.

Democrats, though, were caught off guard by Trump’s willingness to take their side at the expense of the Republicans. As they tried to weigh the significance of the agreement, many were still stunned by the president’s abrupt turnaround.

“A whole lot of them are still in a state of shock,” said Rep. Emanuel Cleaver (D-Mo.). “Some people are going to be taking treatment with their psychiatrist later on today, and some of the others are thinking this is some kind of a nightmare and we're going to wake up and find out that that didn't happen.”