July 16, 2026


Biglaw's Trump-Era Deals Prove Costly as Legal Battles Resume

In a stark revelation, the notion that settlements with Donald Trump might provide legal respite has been sharply debunked. According to Walter Olson, a senior fellow at the Cato Institute, engaging in agreements with the former president does not guarantee any firm the tranquility or certainty it might seek. Olson’s comments came in light of recent subpoenas issued to nine prominent law firms by the Justice Department, a move that has reopened old wounds in the legal community.

These firms, which include legal giants such as Paul, Weiss; Kirkland & Ellis; and Latham & Watkins among others, had previously brokered deals with Trump in an attempt to sidestep the repercussions of his controversial executive orders. The intent was to mitigate the legal and constitutional challenges posed by Trump's directives. However, these agreements appear to have fallen short of providing the firms with any lasting shield against legal scrutiny or the former president's capricious wrath.

The subpoenas are reportedly tied to the actions of Trump lawyer, Boris Epshteyn, who was instrumental in orchestrating these agreements. This development suggests a significant legal entanglement that could unravel much about the nature of the deals struck during Trump's tenure, questioning their legality and the ethical implications for the firms involved.

The legal battles and the scrutiny that these firms now face underscore a critical oversight in their strategy with Trump-related dealings — the underestimation of ongoing legal risks and the overarching reach of presidential discontent. As these firms navigate the complexities of these renewed legal challenges, the broader legal community will be watching closely, gleaning lessons about the risks of political entanglements in legal practices.

This turn of events serves as a cautionary tale to the legal industry, reminding practitioners that deals with high-profile political figures like Donald Trump come with unpredictable risks and that the shadow of such agreements can loom long after they are made. The unfolding legal proceedings will likely offer further insights into the dynamics of such deals and set precedents for how similar cases might be handled in the future.