WASHINGTON, DC - SEPTEMBER 06:  U.S. Senate Minority Leader Chuck Schumer (D-NY) (L) makes a point to President Donald Trump in the Oval Office prior to his departure from the White House September 6, 2017 in Washington, DC. President Trump is traveling to North Dakota for a tax reform event with workers from the energy sector.  (Photo by Alex Wong/Getty Images)
Schumer, Trump embrace in Oval Office picture
01:45 - Source: CNN

Editor’s Note: Errol Louis is the host of “Inside City Hall,” a nightly political show on NY1, a New York all-news channel. The opinions expressed in this commentary are his own.

Story highlights

Errol Louis: No surprise that Schumer and Trump made deal on debt ceiling. The two go back -- are dyed-in-wool NY dealmakers

Louis: Republicans who expected Trump to box out Democrats just got a wake-up call

CNN  — 

President Trump’s abrupt and unexpected decision to cut a deal with Democratic legislative leaders Sen. Chuck Schumer of New York and Rep. Nancy Pelosi of California – an agreement to fund disaster relief and avoid a showdown by increasing the national debt limit – shocked Republican leaders.

But the deal should have come as no surprise, particularly to those who know something about Trump and Schumer: the two have a relationship that goes back decades. And despite their occasional political differences, the Republican President and the Democratic senator have a lot in common.

Both are dyed-in-the-wool big-city operators who came of age in the hothouse of New York politics, a place where trading favors and making, breaking and cutting deals – the bigger, the better – is all in a day’s work.

The two men, born five years apart, were both raised in New York City, and both made their names in politics early on.

Schumer attended James Madison High School, the same remarkable public school as Supreme Court Justice Ruth Bader Ginsburg, Sen. Bernie Sanders and ex-Sen. Norm Coleman. Immediately after graduating from Harvard Law, Schumer ran for a seat in the state legislature and won at age 23.

Around the same time, Trump first made his mark by cutting a deal with New York City officials to convert an ailing hotel, the Commodore, into a glass tower reborn as the Grand Hyatt. As the New York Times later noted, “The project set the pattern for Mr. Trump’s New York career: He used his father’s, and, later, his own, extensive political connections, and relied on a huge amount of assistance from the government and taxpayers in the form of tax breaks, grants and incentives to benefit the 15 buildings at the core of his Manhattan real estate empire.”

Thus began Trump’s career of wheeling and dealing with government officials – including Schumer. Trump and members of his family have donated over $80,000 to Schumer over the years. In fact, at the time he began running for president, Trump had given more to Schumer than to any other US senator. “I’ve known Schumer for many, many years,” Trump said during the campaign. “And I have a good relationship with him.”

That relationship was strained to the breaking point during the early months of the Trump administration. When Schumer teared up at a press conference denouncing Trump’s ban on travel from a handful of majority-Muslim countries, calling the measure “mean-spirited,” Trump openly mocked him.

“I noticed Chuck Schumer yesterday with the fake tears,” Trump said. “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.”

The two have also clashed over Trump’s appointments. Schumer, a master of parliamentary procedures, has blocked or delayed dozens of confirmations, drawing condemnation from the White House.

Despite the ups and downs of their tumultuous relationship, Trump and Schumer share a love of the political game: a deep satisfaction from wheeling and dealing.

Trump, enamored of the rush of negotiating, famously tweeted in 2014: “Deals are my art form. Other people paint beautifully or write poetry. I like making deals, preferably big deals. That’s how I get my kicks.”

Schumer has a similar reputation. “I’ve had a good experience working with Chuck Schumer. I think he’s a guy who likes to get things done, he likes to make deals,” is how Sen. John Thune, an arch-conservative lawmaker from rural South Dakota put it in 2015. “I think he’s a guy we can do business with.”

As far back as 2011, Schumer was teaming up with Republican Sen. Lamar Alexander of Tennessee to bring Republican and Democratic lawmakers together for social meetings at a room inside the Capitol dubbed the Inner Sanctum – a way to create personal relationships and make bipartisan deals easier.

Republicans who expected Trump to box out Democrats and play a traditional GOP game of threatening to block spending – or even risk shutting down the government – just got a wake-up call.

In Schumer the President may have discovered the hometown former pal who loves deal-cutting just as much as he does.