Why K Street is now living in fear of Trump’s retribution campaign

Donald Trump’s attempt to jawbone Microsoft into firing former Biden DOJ official Lisa Monaco as a top D.C. operative has put K Street on high alert about who they hire.

Much of the private sector is paralyzed by Trump’s broader efforts to leverage the might of the government to bend companies to his whims. But that pressure is magnified in government affairs shops across Washington, where corporations are desperate to curry Trump’s favor and avoid his wrath.

“Anything that comes across my desk now is like, ‘What Republican can we hire? And is the Republican MAGA?’” said Jeff Forbes, a founding partner at the lobbying firm Forbes Tate Partners. The job market is so precarious in the Trump era, he added, that it’s been tough for even moderate Republicans to get land a big influence job in Washington, let alone Democrats.

In a town where political connections to whomever is in power amount to currency, it’s not unusual for corporate lobbyists to cycle out of prominent roles when their party loses power.

But “to have a target on your back because of past political affiliation in what has traditionally been a very nonpartisan area is a totally new dynamic,” said one veteran Democratic consultant.

Facebook parent company Meta, for example, has gone all-in on Republicans, elevating the company’s longtime emissary to the right, Joel Kaplan, to head up its policy operations. Meta also added longtime Trump ally and Ultimate Fighting Championship CEO Dana White to its board, and teamed up with conservative anti-DEI crusader Robby Starbuck to root out ideological “bias” from its AI infrastructure.

To some tech industry watchers, there were signs from the start that Microsoft was aware of how hiring Monaco might play in the current climate.

Monaco, who served as Biden’s deputy attorney general and oversaw the department’s various inquiries into Trump’s alleged election interference and mishandling of classified documents, was announced this summer as Microsoft’s president of global affairs.

The company announced her arrival in tandem with the news of a promotion for one of the company’s most prominent Trump alums, former Trump trade official CJ Mahoney. One Silicon Valley player, who like others in this story was granted anonymity to speak candidly about sensitive conversations, suggested that the move from Microsoft signaled “they probably knew there was some risk there.”

Months earlier, Monaco was among more than a dozen Democratic figures who had their security clearances revoked by Trump. Then last Friday, the president went even further.

“It is my opinion that Microsoft should immediately terminate the employment of Lisa Monaco,” Trump wrote in a post on his social media platform, calling it “unacceptable” that Monaco might have access to “highly sensitive information” as part of her role, “especially given the major contracts that Microsoft has with the United States Government.”

Microsoft has yet to comment publicly on Trump’s demands. But Laura Loomer, the conservative activist who has spearheaded the ouster of scores of members of Trump’s administration for insufficient loyalty, didn’t mince words as she took credit for bringing the tie to Trump’s attention. “Are you going to comply?” she asked in a post on X, tagging Microsoft chief executive Satya Nadella.

Microsoft has been awarded more than $2.7 billion in government contracts since the 2020 fiscal year, according to federal spending data, which gives an administration more leverage in these kinds of situations.

“This administration rewards companies that demonstrate political loyalty, and when it comes to federal cloud contracts, Oracle’s CEO, Larry Ellison, is in the catbird seat,” tech consultant Niki Christoff noted.

Nu Wexler, an industry consultant whose resume includes stints at Facebook and Google, said that Microsoft is somewhat more insulated from political pressure compared to other tech giants given that “their products are already deeply embedded in federal systems.”

This isn’t the first time Trump or his allies have tried to engineer the ouster of someone perceived as a foe — even in the private sector.

In August, Trump demanded the resignation of Intel CEO Lip-Bu Tan, before reversing himself days later and leveraging it into a financial stake in the company.

And in April, Chris Krebs, a top cybersecurity official during Trump’s first term, stepped down from his role as chief intelligence and public policy officer at the cyber firm SentinelOne. His move came after Trump revoked security clearances held by Krebs and the firm. Krebs was fired for contradicting Trump’s claims that the 2020 election was stolen.

And it didn’t take long after Biden’s former Defense Secretary Lloyd Austin launched his consulting shop Clarion Strategies this summer to experience MAGA’s pressure campaigns.

When Austin’s firm signed defense contractor General Dynamics, Loomer seized on its hire of a firm “founded by rabid Trump haters” and elevated the matter all the way to Trump’s Defense Secretary Pete Hegseth. Loomer eventually reported that she had received personal assurances from senior leaders at General Dynamics that the contract with Clarion had been scrapped.

Still, there aren’t many former Biden officials of Monaco’s standing working in-house for corporate giants.

Biden’s first White House chief of staff, Ron Klain, is the chief legal officer at Airbnb, but the short-term rental giant does much of its advocacy work at the state and local level. And it doesn’t have nearly the level of exposure as Microsoft does with its role as a top federal contractor.

That has some advisers to corporate America treating Monaco’s case as an outlier.

“I think Lisa's probably in a one-of-one kind of situation,” one Republican on K Street argued. “The president and his team have a naughty list of people who were involved in … whatever you want to call it, Russiagate, or whatever,” added the lobbyist. “It's a pretty short list.”

But there have been other pressure campaigns that have targeted Democrats for much less.

In one, Shelly O’Neill Stoneman stepped down from her role as the top lobbyist at defense and aerospace giant Lockheed Martin weeks before Trump was sworn into office. Her move came after Breitbart highlighted several of her old tweets expressing political positions held by much of the Democratic Party.

Among the messages that put O’Neill Stoneman on the chopping block were ones praising the Biden administration’s move to allow transgender people to serve in the military; discussing the merits of diversity and referring to the Jan. 6 attack as an “insurrection.”

A Lockheed spokesperson reiterated that, “as we shared at the time, Shelly resigned for personal reasons.”

Earlier this month, the defense giant announced its new hire to fill O’Neill Stoneman’s role — Robert Head, a former chief of staff to former GOP Rep. Kay Granger. And in June, Lockheed brought on Jalen Drummond, a former White House spokesperson in Trump’s first term, to serve as vice president of corporate affairs and international communications.

Washington’s influence industry is watching closely for how Microsoft responds to Trump’s threats regarding Monaco. It’s the latest manifestation of a threat that’s been hanging over corporate America since Trump’s first term in office, but has only escalated during his second presidency.

“This will be a very interesting test for Microsoft and other companies at where they draw the line,” said one political consultant who works with tech executives in Silicon Valley.

“At a certain point, these executives will have to question, ‘Can we let this guy tell us how we run our business or not?’”

Since soon after Trump’s win in November, Washington’s consulting class has been advising clients to scrub their websites or other outward-facing media to remove anything that could attract unwanted attention — including references to things like diversity, equity and inclusion initiatives, climate change or immigration.

Corporate America is still searching for the best way to stay on Trump’s good side, which has largely amounted to a combination of trying to stay under the radar while being vocal about wins that could reflect well on Trump.

That caution has trickled down into lobbying hires as well.

“A lot of companies are being extremely careful and selective about who they hire, who they put forward” for jobs in their D.C. offices, according to the Democratic consultant.

It’s more important than ever for companies to weigh how regularly a prospective hire might be interfacing with the Trump administration or external stakeholders, the consultant noted.

“It's really had a very, very chilling effect,” they said.

Jessie Blaeser contributed to this report.