'Resistance is futile': Big Law’s Trump deals face fresh scrutiny after Democrats’ midterm wins

Law firms that struck deals with Donald Trump to escape his campaign against Big Law face a fresh reckoning in Washington, as Democrats prepare to take control of Congress with greater power to investigate the agreements.

Jamie Raskin, the Democrat set to chair the US congressional committee overseeing justice and legal affairs, has said he is ready to subpoena firms that promised pro bono work for the president’s favoured causes to neutralise punitive executive orders, The Wall Street Journal reported.

‍Kirkland & Ellis and Skadden are among the firms already facing demands for documents and explanations over their arrangements with the administration from Raskin and Democratic lawmakers Richard Blumenthal and Adam Schiff.

Their party’s midterm victories will give those inquiries new teeth: control of committees, the power to issue subpoenas and a platform for public hearings when the new Congress convenes in January 2027.

Resistance, for the most part, is futile

Some of the firms now in the crosshairs have built practices helping clients navigate congressional scrutiny, and have themselves warned of its reach and consequence.

In a November 2010 memo titled: 'How to Survive a Congressional Investigation', Skadden warned that "collateral damage [from an investigation] can be devastating to a company’s business". The memo also advised clients who may wish to find a way to stop the investigation that “resistance, for the most part, is futile”.

A December 2018 Paul Weiss memo, listing then-chair Brad Karp among its authors, offered a similar warning. Discussing investigations targeting Trump and his administration, it said: “Corporations may be caught up in these inquiries - and face significant reputational, business, and legal risks - if they have ties to the administration”.

Paul Weiss subsequently became the first firm to strike a deal with Trump, with the firm agreeing to provide $40 million in pro bono advice to his administration.

Kirkland’s congressional investigations practice leader Reg Brown offered a more visceral assessment. In a June 2024 interview with Law360, republished by the firm, he said: “The risk of these matters is extraordinary.” He added: “It’s an easy place to develop an ulcer.”

Companies are already hiring lawyers to prepare for the expected wave of inquiries. Akin, Arnold & Porter, Crowell & Moring and Quinn Emanuel are among the firms engaged to help businesses assess their exposure and prepare for scrutiny, the WSJ reported.

Demands for answers

For Kirkland, the scrutiny extends beyond its $125 million pro bono commitment. In a letter dated 15 October 2026, Raskin, Blumenthal and Schiff sought answers about its alleged efforts to poach lawyers from Paul Weiss while that firm faced Trump’s executive order; its dealings with Trump’s personal lawyer Boris Epshteyn; and its provision of legal services to the Commerce Department.

The lawmakers said Kirkland had “failed to produce a single responsive document” and had declined to meet congressional staff. They challenged its reliance on attorney-client, executive and settlement privilege to withhold information.

Kirkland’s position, as described in the correspondence, is that the requests implicate confidential client information and protected negotiations with the administration. The lawmakers dispute those arguments, including whether privilege could shield details of clients, hours worked and the value of services provided.

Skadden faces questions of its own. In July, the same lawmakers pressed it over potential conflicts arising from its advice to Intel on the government’s acquisition of a 10% stake in the company, alongside reports that it advised the Commerce Department on other matters.

The lawmakers requested a "detailed explanation of how Skadden’s advising of Intel in its transaction with the Trump Administration did not constitute a violation of the Rules of Professional Conduct."

Both Kirkland and Skadden have been approached for comment and asked whether they responded by the deadlines set in the correspondence: 29 October for Kirkland and 4 August for Skadden.