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Chuck Schumer and Donald Trump.
The most intriguing relationship in Washington is finally getting interesting.
President Donald Trump's decision to shun his own party and strike a deal with Senate Minority Leader Chuck Schumer, and House Minority Leader Nancy Pelosi surprised both Democrats and Republicans.
The trio made an agreement to tack on a three-month suspension of the federal debt ceiling - and a continuing resolution to fund the government through early December - to a bill that would also include money for Hurricane Harvey relief.
That agreement, which was reached between the three during a White House meeting with Democratic and Republican congressional leaders, flew in the face of what House Speaker Paul Ryan and Senate Majority Leader Mitch McConnell were advocating for, though McConnell later said Democrats were too quick to celebrate.
It also brought to the forefront that aforementioned relationship between Schumer and Trump.
It was a relationship many were curious to see play out following Trump's shocking victory last fall. As The Washington Post noted in November, "the dynamic to watch" play out in the Senate "could actually be between Trump, the self-described master negotiator," McConnell, and Schumer.
Shortly after his victory, Trump praised Schumer, a fellow outer-borough New Yorker, as someone with whom he "had a good relationship," saying he is "far smarter" than the man he was succeeding as Senate minority leader, Harry Reid.
"He is far smarter than Harry R and has the ability to get things done," Trump tweeted. "Good news!"
It wasn't the only time last year Trump talked up his ability to work with Schumer.
Last January, Trump told MSNBC's "Morning Joe" that, if elected, he would "be able to get along well with Chuck Schumer."
"I was always very good with Schumer," Trump said. "I was close to Schumer in many ways."
One way, at least on paper, happened to be Trump's past donations to Schumer's campaigns.
Schumer happened to be the sitting member of Congress that Trump personally donated the most money to, according to Federal Election Commission filings. Over the past three decades, Trump donated roughly $9,000 directly to the New York Democrat's campaign. Three of Trump's children - Eric, Donald Jr., and Ivanka - donated a combined $6,800 to Schumer. Jared Kushner, Ivanka's husband and a White House senior adviser, donated $4,000 to Schumer.
"I mean, I've contributed to Schumer, I contribute - I've known Schumer for many, many years," Trump said last year. "And I have a good relationship with him. The fact is, that I think it is time maybe that we all do get along."
And at last year's Al Smith dinner in New York, Trump joked that Schumer "used to love me when I was a Democrat."
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Mike Pence, Trump, and Schumer.
For his part, Schumer has worked to downplay any appearance of a relationship between the two. But going into the Trump presidency, he did leave the door open to making deals on issues where Democrats found themselves closer to Trump's outlook than they did congressional Republicans.
"He was not my friend," Schumer told Politico last fall following Trump's election. "We never went golfing together, even had a meal together. He's called me, we've had civil conversations a couple of times. But I've got to see what he does."
"When we can agree on issues, then we're going to work with them," Schumer said last fall. "But I've also said to the president-elect on issues where we disagree, you can expect a strong and tough fight."
That tough fight is exactly what ended up happening. Instead of starting his presidency working on a campaign pledge such as increased infrastructure spending, an area where he could find common ground with Schumer and Democrats, Trump's first legislative item was replacing the Affordable Care Act, President Barack Obama's signature legislative achievement. Schumer found himself among those leading the Democratic Party's opposition to the Republican healthcare effort, which eventually failed in the Senate and was subsequently quashed.
Schumer too was outspoken about the multiple ongoing investigations into Russian interference in last year's presidential election. At least one of those investigations is probing whether members of the Trump campaign worked with Russian officials to influence the election. And Schumer was at the frontlines of battles against Trump's travel ban, his nomination of Supreme Court Justice Neil Gorsuch, and, more recently, in denouncing the president's comments on the racist attacks and white nationalist protests in Charlottesville, Virginia last month.
Within the first few days of the Trump presidency, it became clear that any possible working relationship between the two would be virtually non-existent.
"I noticed Chuck Schumer yesterday with the fake tears," Trump told reporters in January about a video of Schumer tearing up alongside Muslim refugees as he was denouncing the president's travel ban. "I'm going to ask him who was his acting coach, because I know him very well. I don't see him as a crier."
"If he is, he's a different man," he continued. "There's about a 5% chance it was real. But I think they were fake tears."
But that all appeared to take a turn - however brief it may be - with last week's deal.
In its aftermath, Trump was speaking in glowing terms about the deal and his partners in it, "Chuck" and "Nancy." He told reporters that he thinks "you are going to see a much stronger coming together," and that the deal signaled that more bipartisan action could be on the way.
"I think we will have a different relationship than we've been watching over the last number of years. I hope so," Trump said. "I think that's what the people of the United States want to see. They want to see some dialogue."
Trump too appeared to bask in the coverage of the deal, which was given positive reviews in both pro-Trump and mainstream outlets. As Schumer told The New York Times, Trump called him to boast of the deal's reception in the press.
"He said, 'This was so great!'" Schumer said. "Here's what he said: 'Do you watch Fox News?' I said, 'Not really.' 'They're praising you!' Meaning me. But he said, 'And your stations' - I guess meaning MSNBC and CNN - 'are praising me! This is great!'"
Highlighting Trump's sentiment regarding the cable coverage, Jesse Ferguson, a Democratic staffer who was a top spokesperson for the Clinton campaign, told Business Insider that the deal itself hasn't changed much in the relationship between Trump, Schumer, and other Democratic leaders.
"In the end, Donald Trump doesn't have an allegiance with anyone other than Donald Trump's ego," he said. "So, if you want to get something, this deal is the latest proof that if you want to get Donald Trump to do something, show him that he will be praised on cable news for it, and he will do it."
"That's always been the reality of Trump," he continued. "And so I think what is going forward, it's a reminder that the legislative strategy focused on the policy merits is never the way to win this White House's support. A legislative strategy focused on throwing a ticker-tape parade for the president is far more likely to be successful."
But Ferguson said he continues to "hold out hope" that Trump will be able to work with Democrats to pass a massive infrastructure passage, something that could be a product of a productive Trump-Schumer relationship.
"Democrats will get to create jobs and rebuild America's infrastructure, and we'll just have to let every bridge and every road be named after Donald Trump in order to get it passed," he said. "I don't think that's anything new. That's been true the whole time."
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Schumer.
At an Oval Office meeting with New York and New Jersey leaders the day after the surprise deal was struck, Schumer and Trump engaged in what longtime Republican Rep. Peter King of New York described as "a love-in."
"He and Chuck - both of them would interrupt each other at times - and they'd go back and forth and Chuck would say something and smile and the president would look at him and smile," King told CNN. "This went on for the whole - let's say the meeting was around 40 minutes or so? It was almost like a love-in at times."
Calling the deal "a good moment" that he would like to see continue, Schumer joked that he believed Trump was "a little tired of the partisanship, too, even though frankly he caused some of it."
Speaking to the Times, Schumer said the White House may be "learning, either instinctively or intellectually, that just embracing the hard right isn't going to get them very far."
Many Republicans, particularly strong supporters of Trump, have framed the deal as a "warning shot" at Republican leadership. Trump, they say, is tired of nothing getting done, and this deal provided him with the chance to both get something through Congress and send a message to his team.
"It will serve as a warning shot," Barry Bennett, a Trump campaign adviser, told Business Insider. "Pursuit of perfection is not an excuse for failure. Congress had an 8% approval rating even including their friends and families. We are in charge of everything. We best figure out how to drive."
Matt Mackowiak, a Republican strategist and president of the Potomac Strategy Group, told Business Insider that the "unpredictable" Trump's "recent alliance with Schumer was born more of a desire to get a win than to achieve a specific policy victory."
He noted that the three-month delay on the debt ceiling and the spending bill "will be quickly forgotten."
"What matters is the end game in December," he said. "Trump thinks this deal was good for him and now I suspect Schumer and Pelosi are proposing other deals. The details matter and the President needs to focus on the specifics or his coalition will fracture. Congressional Republicans were forced to swallow this recent deal due to the inclusion of the Harvey relief money, but there is no guarantee they will sit on their hands the next time, particularly if the deal is a policy loser for conservatives."
And Democrats aren't all dancing as a result of the agreement.
"President Trump is transactional, capricious, and terrified of failure - he's both manipulative and vulnerable to manipulation," Jesse Lehrich, a Democratic operative who worked as a Clinton campaign spokesperson, told Business Insider. "There's no reason leaders Schumer and Pelosi shouldn't continue looking for areas where they can work with the president, but they should proceed with great caution and distrust."
"This is a man who sees in others nothing more than temporary utility, and he takes joy in publicly humiliating those who no longer serve a purpose for him, especially if he feels they've wronged him," he continued.
But as Schumer acknowledged, the pair do have their New York roots to fall back on in any setting, something that some believe gives the Democratic leader a leg up on Ryan and McConnell when all are in the process of negotiating with Trump.
"The one thing we have is we're New Yorkers," Schumer told the Times. "We're pretty direct, and we talk right at each other."
Ferguson, however, thinks that aspect is oversold.
"Relating with Donald Trump is much more about ego than accents," he said. "I don't think it matters whether you're talking in a Kentucky, a midwest, or a New York accent - if Mitch McConnell offered to rename the RNC building after Donald Trump, the president would suddenly be far happier with Mitch McConnell's leadership."