On Wednesday, Donald Trump came to Washington. It was not his first visit.

Trump plays the political outsider. “Washington is broken,” he declared in Iowa in January as he positioned himself to run. But he has been a Washington insider longer than almost any of his rivals.


Since the 1980s, he has lavished both parties with money. He’s employed D.C. lobbyists and aggressive tactics to influence politicians and further his business interests. He’s become comfortable enough with Washington to buy a nearby golf course and develop a hotel on Pennsylvania Avenue, blocks from the White House, in conjunction with the federal government.

Even as he rails against corruption in American politics, his long history with Washington and lobbying raises questions about his promises to change the system of influence-peddling he has participated in for decades.

“I don’t fault him for having to work within the system that he’s dealt,” said former Republican Rep. Chris Shays, who met with Trump a decade ago over the businessman’s efforts to expand gambling in Connecticut. “I’d fault him for implying that somehow he’s different, because there’s nothing different about him.”

Veteran Republican lobbyist Charlie Black, whose old firm Black, Manafort, Stone and Kelly represented Trump for over a decade, called Trump’s anti-Washington, anti-lobbyist rhetoric “ironic.”

“I like the guy, but he’s never been allergic to lobbyists before this year,” Black said.

The New York developer first employed Washington lobbyist Roger Stone, a veteran of Richard Nixon’s and Ronald Reagan’s presidential campaigns and partner of Black’s, as early as 1980, according to Stone’s recollection.

Stone said he views Trump’s political contributions tied to lobbying efforts -- on everything from the height of his buildings to slots for his planes at Washington’s Reagan National Airport and tribal recognition for would-be Native American casino operators -- as a necessary part of doing business.

“It’s not that there’s a quid pro quo, but they don’t even listen to you unless you’re a donor,” said Stone, who left Trump’s presidential campaign last month under disputed circumstances but continues to support his candidacy and maintains that Trump’s wealth gives him an independence that makes him more likely to reform the political system than his rivals.

A Trump spokeswoman did not respond to multiple requests for comment.

In 1987, Trump’s status as a Washington insider was cemented when Democrats decided they wanted a piece of the then-Republican developer’s money and his Reagan-era, rich-guy swagger. Democratic Speaker of the House Jim Wright visited Trump in New York and asked him to host the Democratic Congressional dinner, the DCCC’s largest fundraising event of the year.

Then-Sen. John Kerry ‑- architect of the Iran deal Trump came to Washington on Wednesday to condemn and whose bicycling hobby Trump regularly mocks – called Trump to ask him consider hosting the dinner.

''He sees Trump as an independent thinker who can put this thing together,” explained a Kerry spokesman at the time.

The Democratic wooing was not in vain.

By 1993, when Democrats took control of the White House, Trump’s allegiance had shifted with the political winds, and he paid $15,000 for a table at the dinner. That year he gave $5,000 to the defense fund of Democratic Rep. Dan Rostenkowski of Illinois after U.S. Attorney Eric Holder indicted him on corruption charges (Rostenkowski would plead guilty and later received a pardon from President Bill Clinton).

Also that year, lawmakers from Nevada arranged for Trump to meet with Democratic Speaker of the House Thomas Foley (Wright had resigned the speakership amid an ethics investigation) and various committee chairmen in an effort to limit the rise of Native American-run casinos, including one proposed operation in New Jersey, which threatened Trump’s gambling interests in Atlantic City.

In 1995, Republicans regained control of Congress and Trump began giving them a significant portion of his political contributions again. That year, Trump implied that his influence was behind an effort by House Republicans to impose corporate incomes taxes on Native American gambling businesses – saying he had talked to Ways and Means Committee members about the issue, but declining to name names.

Democrats on the committee nicknamed the measure the “Trump amendment,” the New York Times reported at the time.

Trump also regularly dispatched his D.C. lobbyists to deal with state-level interests, and sometimes found himself under investigation. In 2000, Trump, Stone and their associates paid a $250,000 fine to the New York state lobbying commission, the largest ever levied by the body at that point, for failing to register lobbying activities after they secretly funded a campaign to undermine the gambling ambitions of Mohawk Indians in the state.

They did not admit wrongdoing, and Stone said he believes Trump would have prevailed on first amendment grounds if he had not decided to settle.

Trump eventually concluded that he could not beat the Native American gambling industry, so he decided to try to join it.

A onetime opponent of expanding federal tribal recognition – he famously said some groups seeking that status “don’t look like Indians to me” during congressional testimony in 1993 – he helped finance efforts by Connecticut’s Eastern Pequots to gain recognition in 2004 in the hopes of getting a piece of any future tribal gambling business.

Shays, who opposed expanding gambling in Connecticut and Trump’s efforts to circumvent congressional power over tribal recognition by going straight to the Bureau of Indian Affairs, met with Trump in the mogul’s New York offices to discuss the matter.

“He came across to me as someone who’s dealt with a lot of politicians,” said Shays, who described Trump as “very pleasant.”

Trump evidently felt positively enough about the culture of Washington to purchase a golf course in northern Virginia in 2009 and rebrand it as “Trump National Golf Club, Washington, D.C.”

In 2011, Trump attended the White House Correspondents’ Dinner, where President Obama and comedian Seth Meyers made him the butt of many of jokes.

Though he did not appear to enjoy the ribbing, he was still game to do business with the Obama Administration.

In 2012, Trump won a contract from the General Services Administration to develop a luxury hotel at the Old Post Office Pavilion, a marquee property in the heart of D.C., despite competition from global hospitality empires – a feat he often touts on the stump.

Trump’s upset stunned the other bidders, according to a person familiar with the bidding process. “Hilton is one of the biggest hotel companies in the world. Marriott, Hyatt competed. It didn’t make sense. This is a taxpayer asset. You look at the record of bankruptcies and failures,” said the person, referring to the four times Trump has declared corporate bankruptcy.

But as Trump bragged recently about his ability to get the government to favor his business interests, "Nobody played the game better than me. I was the king."

Stone said Trump’s active participation in a system that demands contributions in exchange for political favors should not set a higher bar for him to convince voters that he is the man to reform Washington. “It’s certainly no higher a bar than for any of the other guys on the stage who’ve been gorging on contributions all these years.”