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Trump finds an unlikely partner: Chuck Schumer

Hours after Sen. Chuck Schumer delivered a hopeful speech to anxious Democrats gathered at the Javits Center on Election Night, the dealmaker was already recalibrating to his new, less powerful reality.

Schumer was not displaying any signs of shock, like many of the Democrats around him, who looked like they had been shot in the shoulder when it became clear Hillary Clinton was going to lose the race of her life. The man who long dreamed of ascending to Senate majority leader — and presiding over bill signings with the former junior senator from New York installed as a partner in the Oval Office — was already thinking about how he could shoehorn his grandiose plans into a world where Donald Trump would be president.

Democrats who spoke with Schumer that night and in the following days described him as making an immediate shift to strategizing about how to work with Trump while also identifying where he would oppose him — and trying to talk himself into the idea that the president-elect isn’t really a Republican, but a pragmatist with no apparent ideological mooring.

Privately, the soon-to-be Senate minority leader has opened up a back channel of communication with Trump and, according to Democrats who have spoken with Schumer since the election, he views Trump as someone he can try to maneuver.

Multiple sources said the two have spoken at length about legislation and appointments, in a series of phone calls that began with Trump phoning Schumer the morning after Election Day, to express hope that the two could work together.

Since then, according to a source in Trump Tower, they have spoken directly a “handful” of times, discussing policy, appointments, logistics and sometimes even just bantering about New York.

Now, as the debate within the Democratic Party rages about whether to seek common ground with Trump, or to steal a page from the playbook of Senate Majority Leader Mitch McConnell, who vowed to make Obama a one-term president and successfully blocked many of his nominees, including his Supreme Court pick Merrick Garland. Schumer seems to be leaning toward the former.

Schumer, by nature, is a dealmaker, not an ideologue — and insiders said he’s more interested in keeping open a line of conversation with Trump Tower in the hopes of holding the seats of the 10 Democratic senators up for reelection in 2018 in states where Trump won, a move designed to protect his caucus.

Trump and his top aides are, in some ways, built the same way. On Friday morning, at a breakfast hosted by the Partnership for New York City at Morgan Stanley in Manhattan, Trump’s son-in-law and top adviser Jared Kushner appeared at a back-to-back panel with Schumer, according to a source in the room. There, Kushner agreed with the New York senator that the president-elect was closer to Schumer than to McConnell when it came to infrastructure spending plans.

Schumer, for his part, said that Democrats screwed up during the election in part because they need to move closer to Trump on trade.

The open conversation and points of agreement are what give Schumer hope of finding some common ground. But with Republicans controlling 52 Senate seats to Democrats’ 48, Schumer is facing a daunting task of trying to preserve some of President Barack Obama’s legacy — including Obamacare, Dodd-Frank financial reforms, the Iran nuclear deal and climate regulations.

“He’s a hard partisan fighter who knows how to win and wants to win seats, but also wants to put deals together and get things done,” said one former Schumer aide. “He has very few permanent enemies in this town.”

While Schumer told POLITICO in an interview last month that his fellow New Yorker “is not my friend,” Schumer and his team have had more interaction with Trump’s team than almost any Democrat has to date, save for Obama. The two leaders have plans to have a face-to-face meeting in the near future, but have yet to settle on a date.

And they’re already cutting deals. Trump called Schumer seeking his advice about whether U.S. Attorney Preet Bharara would be willing to stay on, according to a source familiar with the discussions. He had seen the showy U.S. attorney dominating the pages of the tabloid newspapers with his independent investigations into the state’s top Democratic leaders, and was impressed, sources said.

Schumer acted as the go-between, reaching out to Bharara, his former general counsel, and then connecting Trump and Bharara to set up a pro forma meeting once both parties knew that Bharara would be walking the marble lobby to accept the job extension with a handshake.

In general, Democrats close to Schumer said he does not view challenging Trump directly on a daily basis as necessarily the right strategy to protect his fragile caucus — but also that he plans to push hard on confirmation hearings and be militant in his opposition to repealing Obamacare and going after Dodd-Frank.

But in terms of simply going full war on Trump, one Democrat close to Schumer said: “He will leave that to the external groups, and look for ways to work together.”

“He will start from what’s the end point and work backwards,” said the former Schumer aide. “He certainly won’t close off that type of conversation. He’ll be open to conversation. He will pick his spots and find places to stand up to Trump and fight till the last dog dies.”

Spokesmen for Schumer and Trump declined to comment.

Since the election, Schumer has been soliciting advice from longtime advisers about what the Democratic Party needs to do to rebuild, and talking out his own post-mortem with Clinton allies, on his flip phone, about what, exactly, they did wrong, according to people who have spoken with him.

And on the immediate question of how to engage Trump, longtime Democrats say there’s no easy answer.

“There will be those who counsel unrelenting warfare, who will be nervous about their relationship and will fear handing Trump victories,” said David Axelrod, a former senior adviser to President Obama. “And there is a theory that there could be wedge issues on which Trump may side with Democrats and cause disruption among Republicans.”

Schumer’s stance is, for the most part, in line with members of his caucus — even progressive Sens. Elizabeth Warren and Bernie Sanders have said they will look for opportunities to work with Trump and his administration.

Publicly, Schumer has carefully chosen moments to assume a line of opposition. He has teamed with Sen. John McCain to call for a congressional investigation into the Russian hackers’ meddling in the election. And in a statement to The Washington Post, Schumer said Trump “is rigging the Cabinet top to bottom with allies of the oil industry.”

In the interview with POLITICO last month, Schumer distanced himself from Trump, his fellow outer-borough-born New Yorker who, along with his family, has donated more than $20,000 to Schumer’s campaigns over the years.

“We never went golfing together, even had a meal together,” he said. Longtime aides don’t recall them ever working together — Schumer has close real estate friends in New York, like the Tisch family. But Trump was never part of his world, as much as someone else passing cordially through the same monied Manhattan corridors as they both went about their New York business. (In 2008, however, Schumer attended a glitzy fundraiser for Senate Democrats at Trump’s Mar-a-Lago estate in Palm Beach.)

Trump talks to House Speaker Paul Ryan every day. And his incoming chief of staff, Reince Priebus, talks to McConnell almost daily. But Trump aides also see the benefit of a channel to the Democratic minority leader. “When it comes to Washington, you can ignore the House, but you can’t ignore the Senate, and there are people around Trump who understand that well,” said a source close to Schumer.

“I have always had a good relationship with Chuck Schumer,” Trump tweeted on Nov. 20, after the two had spoken a few times on the phone. “He is far smarter than Harry R and has the ability to get things done. Good news!”

Schumer’s strategy for his party’s survival is not one that all Democrats agree with.

The fear among some progressives is that dipping in and out of fights with Trump will lead to a schizophrenic impression of the party. “Schumer’s in a tough spot because there hasn’t been this much distrust of the Democratic establishment in generations,” said Democratic strategist Rebecca Katz, a partner at Hilltop Public Solutions and a former aide to New York City Mayor Bill de Blasio and outgoing Senate Minority Leader Harry Reid. “If you leave Washington, D.C., it is much harder to find Democrats who want to compromise or seek incremental wins. Many want to fight.”

Some Democrats were also frustrated with Schumer’s more moderate pose during the campaign, which they think feeds into efforts to “normalize” him. After Reid called Trump a racist, for instance, Schumer hedged, calling him only someone who “is far too tolerant in accepting the support of racists.”

But his moderated stance, and shared home state, leave the relationship between Schumer and Trump one of the most critical in Washington, and one with the most possibility.

The two New Yorkers recognize in one another a practical dealmaker with a deep understanding of how news works — bred through years of soliciting their own coverage in the local New York City papers.

For decades, New Yorkers have watched the two master manipulators of the press share the pages of the same newspapers — Trump dominating the New York Post’s Page Six with glitz and controversy; Schumer slogging through weekly Sunday press conferences to feed the tabloid’s page two, where the paper runs the drier, policy-driven headlines.

If Schumer is driven by a desire for credit for every incremental victory — he is famous for issuing a news release on every call to a CEO he is pressuring to keep jobs in New York, much like Trump did touting the Carrier Manufacturing jobs deal — it’s because he wants to be understood as a tireless fighter for the middle class in New York; Trump’s fixation with the press, over the years, appears to have been driven more by the desire to be seen, and to be the story.

But under the broad brushstrokes that make them look like similar brash New York personalities, there are major differences at their cores: Schumer grew up in middle-class Sheepshead Bay; Trump was raised in the upscale Jamaica Estates of Queens. Schumer would never leave Brooklyn and still spends his weekends riding his bike around the borough he has lived in his entire life; Trump is now a creature of Midtown Manhattan, who rarely travels to the outer boroughs except to get to his private jet.

The common background can help — up to a point.

“In the short term, Democrats are going to expect Schumer to lead fights against some of the Trump appointees and early initiatives, such as tax cuts,” said Axelrod, “and Schumer is going to have to walk a really difficult path.”

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