WASHINGTON — The chief executive of the arms maker Raytheon, under pressure to overcome a congressional hold on major sales in the fall of 2018, wanted to sit down with one of the few people who could solve the problem — Secretary of State Mike Pompeo.
But the State Department would not schedule the meeting. So Raytheon turned for help to David Urban, perhaps the best-connected lobbyist in President Trump’s Washington.
Mr. Urban was a classmate at West Point of Mr. Pompeo and of Mark Esper, now the defense secretary, and was influential in recommending both men for administration posts.
He has close ties to Mr. Trump, who credits him with having helped deliver a pivotal Election Day victory in Pennsylvania in 2016 and recently invited Mr. Urban to fly on Marine One with him to West Point. He has a long roster of blue-chip clients, including military contractors like Raytheon, whose chief executive got the meeting he wanted with Mr. Pompeo after Mr. Urban intervened on his behalf.
It is not known precisely what Mr. Pompeo discussed with the Raytheon executive, but in a few months, the State Department had issued an emergency waiver that circumvented the congressional hold on the arms deals, allowing billions of dollars in Raytheon missiles and bombs to be sold to Saudi Arabia and the United Arab Emirates. The department did not deny that Mr. Urban arranged the meeting but said the emergency waiver — now the subject of congressional and inspector general investigations — was consistent with American national security objectives.
The story behind Mr. Pompeo’s meeting with Raytheon, which has not been previously reported, is emblematic of the outsize influence wielded in Washington by Mr. Urban and a small group of other lobbyists and operatives who backed Mr. Trump when most of the K Street establishment was keeping its distance. Those relationships became lucrative after Mr. Trump won a surprise victory on Election Day and rewarded early loyalists with key posts, continued access or both.
With Mr. Trump lagging in the polls, the lobbyists are seeking to protect that mutually beneficial relationship by working to re-elect him, underscoring the mix of politics and policy that has served them — and their clients — so well over the last three and a half years.
Consider the examples of eight lobbyists and operatives with ties to lobbying firms, including Mr. Urban, who are now assisting Mr. Trump’s campaign in various paid and unpaid capacities, like fund-raising and strategy.
Those eight have been paid a total of nearly $120 million through their firms to influence the United States government from the beginning of 2017, as Mr. Trump prepared to take office, to the end of March, according to an analysis of congressional and Justice Department filings.
The scale of those revenues is especially striking given that several of the lobbyists — including two of the top three earners, Brian Ballard, a veteran lobbyist from Florida, and Jeff Miller, an operative from Texas — had not lobbied at the federal level before Mr. Trump’s election. Mr. Ballard’s firm was paid nearly $65 million and Mr. Miller’s more than $18 million by interests for which the two men had registered to lobby through the end of March, the most recent period for which comprehensive data is available.
And while Mr. Urban has been a registered lobbyist at the federal level since 2002, his federal lobbying revenues have nearly tripled in the Trump era — rising to more than $25 million in the roughly 40 months after his swearing-in from less than $9 million in the roughly 40 months before Mr. Trump became president.
The mutually beneficial relationships between the president and the lobbyists is the latest evidence of the hollowness of Mr. Trump’s 2016 campaign pledge to “drain the swamp” by taking on the special interests, lobbyists and donors who had “rigged the system against everyday Americans.”
Mr. Trump’s political kitchen cabinet is stocked with people who are thriving in that swamp.
They include Corey Lewandowski, Mr. Trump’s initial campaign manager in 2016. Mr. Lewandowski has not registered as a lobbyist, despite advising companies with issues before the administration and also reports that he has worked with a lobbying firm founded in part by Jason Osborne, a former Trump 2016 campaign aide who has raised at least $360,000 for Mr. Trump’s re-election campaign.
Also recently added to the campaign team was Jason Miller, who set up meetings in 2017 for Wall Street executives with cabinet officials, and briefly registered this year as a lobbyist for other companies before joining the campaign’s payroll.
Mr. Urban and Mr. Lewandowski, who have not been paid by the re-election campaign committee, joined Mr. Miller in a campaign brain trust meeting last month, first reported by Axios.
Beyond the strategic advice, Mr. Trump’s campaign has also benefited from financial assistance from lobbyists who are top volunteer fund-raisers, including Mr. Ballard, Jeff Miller, Roy Bailey, David Tamasi and Kent R. Hance of Texas, a former Democratic representative who switched to the Republican Party in 1985 after leaving Congress.
They have been credited with raising a total of nearly $8 million since the beginning of 2019 for Mr. Trump’s re-election committees and the Republican National Committee, according to campaign finance filings, though they most likely accounted for far more cash raised to help Mr. Trump, since the filings only count certain kinds of donations.
There is a long tradition of Washington lobbyists and consultants in both parties assisting campaigns, which helps ensure their continued access to the corridors of power.
Mr. Trump, however, was a Washington outsider with few connections to traditional K Street power brokers, and most kept their distance from him. That has heightened the earning power of the relatively few lobbyists who publicly backed the president, whose support in some cases has won them entree into the inner circles of the Trump administration and campaign.
“This is by far the smallest number of lobbyists supporting a president in decades,” said Mr. Tamasi, a K Street veteran who began raising money for Mr. Trump in June 2016, and has raised more than $230,000 for his re-election effort and the Republican National Committee. “The market sees that limited pool of K Street support and makes advocacy business decisions accordingly.”
Mr. Bailey, who had not registered to lobby the federal government before Mr. Trump took office, highlighted his fund-raising for Mr. Trump’s campaign and inauguration in an email seeking access to Scott Pruitt, then the administrator of the Environmental Protection Agency, for a biotechnology company now known as Precigen. The company paid Mr. Bailey $180,000 in lobbying fees.
Mr. Ballard, who has known Mr. Trump for 30 years and had lobbied for the Trump Organization in Florida, has been hired by a host of major companies seeking to deal with scrutiny from Mr. Trump or his administration, including General Motors, Boeing, Amazon and the Turkish state-owned bank Halkbank.
Mr. Ballard was a leading fund-raiser for Mr. Trump’s 2016 campaign and then for his inauguration. He is a regional vice chairman for the Republican National Committee’s fund-raising operation, and was tapped last month as a co-chairman of the committee raising funds for the recently relocated Republican National Convention in Jacksonville, Fla.
Jeff Miller, who is not related to Jason Miller, had run the 2016 presidential campaign of Rick Perry, the former governor of Texas Mr. Trump later nominated as energy secretary. He helped Mr. Perry navigate the confirmation process, and registered to lobby for his first clients in Washington — including an energy company — one day before Mr. Perry was confirmed and sworn into office, then facilitated meetings for clients with Mr. Perry.
Mr. Miller has raised about $4 million for Mr. Trump’s re-election and the Republican National Committee from the beginning of last year to the end of March.
But few lobbyists consistently have more influence than Mr. Urban, who is known as the master of the subtle nudge, often delivered in private discussions. Mr. Urban declined to comment.
Mr. Trump has called Mr. Urban “one of my good friends.” And a month after the election, during which Mr. Urban ran Mr. Trump’s winning campaign in the crucial swing state of Pennsylvania, the pair were photographed watching the annual Army-Navy football game together in Mr. Urban’s private suite.
Mr. Urban had played football at West Point and, to this day, he carries an olive-drab green Army surplus backpack instead of a briefcase to many meetings. Last year, Mr. Trump appointed Mr. Urban to a position at his alma mater. The public displays of support from the president, which have included multiple flights aboard Air Force One and one last month aboard Marine One, bolstered Mr. Urban’s reputation as well-connected and raised his earning power on K Street.
The two friends he helped place in the Trump administration’s cabinet — Mr. Pompeo, who initially served as C.I.A. director before becoming secretary of state, and Mr. Esper, a former Raytheon lobbyist who served as Army secretary before becoming defense secretary — are now in positions to oversee issues of key importance to Mr. Urban’s military contractor clients.
Mr. Pompeo invited Mr. Urban, as well as the chief executives of two companies for which Mr. Urban lobbies — Raytheon and the convenience store chain 7-Eleven — to exclusive dinners in the State Department’s Diplomatic Reception Rooms.
Mr. Urban’s private conversations with Mr. Pompeo and Mr. Esper tend to focus on politics, rather than foreign affairs or national security, according to people familiar with the relationships. One of the people said Mr. Esper, in particular, has relied on Mr. Urban as a Trump whisperer, who helps interpret the president’s moods and rants.
When Mr. Trump became upset with Mr. Esper’s opposition last month to his threat to send the military to quell unrest in American cities, Mr. Urban expressed support for his former classmate, which played an important role in Mr. Trump’s decision not to remove the defense secretary, according to two people familiar with the discussions.
Other lobbyists say Mr. Urban has further raised his profile with both his clients and Mr. Trump through his platform as a paid contributor for CNN, which appears to have started regularly identifying him as a lobbyist during his appearances on its programs after drawing scrutiny for consistently failing to do so.
During a segment on the network last year, Mr. Urban suggested the possibility of a proportional military response against Iran in retaliation for the country’s downing of a crewless American drone. “If I were a betting man, I’d bet that there’d be some sort of a Tomahawk missile strike on the site that launched this,” Mr. Urban said, referring to one of Raytheon’s products. Mr. Trump had approved a retaliatory strike against Iran in that case but pulled back at the last minute.
And during an appearance this year, after praising Mr. Trump’s hard-line against Iran, Mr. Urban was asked by a CNN host whether a move against Iran might represent “an opportunity for your companies.” Mr. Urban rejected the question, praising the president for being “incredibly restrained with the use of force,” and adding “no one is looking to profiteer here.”
Members of Congress from both parties opposed the Raytheon arms sales to the Saudis, in part because of Saudi Arabia’s leading role in the Yemen war, which has left thousands of civilians dead and millions suffering from famine, and later because of the grisly killing by Saudi agents of the journalist Jamal Khashoggi.
By late summer 2018, Raytheon executives were under increasing pressure to close the stalled deals. At least one of the contracts called for onerous penalties if the company did not deliver, and executives had also already booked the sales as expected revenue, according to current and former government officials.
Thomas A. Kennedy, then the company’s chief executive and now its executive chairman, sought a meeting with Mr. Pompeo that fall, but Mr. Pompeo pushed it to lower-level officials, who met with subordinates of Mr. Kennedy that September, the officials said.
After Raytheon enlisted Mr. Urban, the meeting between Mr. Pompeo and Mr. Kennedy happened in early 2019. Mr. Urban did not attend. The arms sales later proceeded after the State Department issued the emergency declaration overriding the congressional block.
The State Department played down the meeting, noting in a statement from a spokeswoman that Mr. Pompeo meets with corporate executives “with great frequency” and has an entire bureau at the department dedicated to working with the private sector on national security matters.
“The secretary’s decisions with respect to arms sales — as with all of his actions — are made to keep America safe and undergo a full legal review and approval process,” the statement said.
The congressional and inspector general investigations into the emergency waiver and the related arms sales have put scrutiny on Mr. Pompeo. But Mr. Urban’s clout appears to remain intact.
The State Department spokeswoman said Mr. Pompeo “has known David Urban for over three decades and knows him to be an American patriot.”
Kenneth P. Vogel and Hailey Fuchs reported from Washington, D.C., and Michael LaForgia from Spokane, Wash. Eric Schmitt and Edward Wong contributed reporting from Washington, D.C.