In October 1973, a young Donald Trump, then 27 and eager to establish himself in Manhattan real estate, met Roy Cohn, a controversial New York lawyer known for representing figures ranging from mobsters to celebrities. The meeting, which took place at the exclusive Le Club restaurant, marked the beginning of a significant professional and personal relationship that would influence Trump's approach to business and politics.
At the time, Trump and his father faced a federal lawsuit accusing them of discrimination against Black applicants seeking housing in their properties. Seeking advice, Trump reportedly asked Cohn how to respond. Cohn’s blunt counsel was to fight the charges aggressively and make the government prove any wrongdoing, a tactic that resonated with Trump and helped shape his combative style.
Cohn had built his reputation as a ruthless attorney during the postwar Red Scare, serving as chief counsel to Senator Joseph McCarthy. He mastered the art of relentless attacks, denying allegations without conceding any ground, and dominating headlines while leaving little paper trail. These tactics would later become hallmarks of Trump’s own public and legal strategies.
Born into a privileged New York family, Cohn excelled academically and began his legal career at a young age, leveraging his father’s connections. He played a central role in the high-profile espionage trial of Julius and Ethel Rosenberg, who were convicted and executed for passing atomic secrets to the Soviet Union. Despite the widespread shock over Ethel Rosenberg’s death sentence, Cohn remained unyielding and famously declared he would have carried out the execution himself.
Cohn’s principles—never showing regret or doubt and never apologizing—defined his approach throughout his career. His involvement with McCarthy’s aggressive anti-Communist investigations helped destroy the careers of numerous officials before the senator’s own downfall during televised Army-McCarthy hearings in 1954. Despite multiple instances of lying under oath, Cohn evaded prosecution.
After returning to New York, Cohn cultivated relationships with prominent media figures and clients, including representatives of all five of the city’s mafia families. For decades, he escaped legal consequences despite several investigations into his conduct. Cohn’s personal life became more openly secretive after inheriting a townhouse in Upper Manhattan in 1967, which served as both his office and a private social space that some accounts describe as a hub for gay nightlife, though he never publicly acknowledged his sexuality.
By the mid-1970s, Trump was among Cohn’s most prominent clients. Cohn managed aspects of Trump’s real estate ventures, arranged a decidedly favorable prenuptial agreement for Trump’s marriage to Ivana Trump, and introduced him to notable social circles, including the famed nightclub Studio 54. Both men shared a combative, publicity-conscious approach, though one of Trump’s cousins noted that Trump combined narcissism with insecurity, whereas Cohn displayed a more assured self-confidence despite concealing his sexual orientation.
Cohn’s career ended amid mounting legal troubles, culminating in his disbarment on charges including perjury and coercion. Diagnosed with AIDS in 1984, he never publicly acknowledged his illness and died in August 1986. His legacy persists through the influence he exerted on American political tactics and culture. Some observers argue that the aggressive, confrontational style Cohn pioneered has left an enduring imprint on the political landscape, epitomized by figures such as Trump.