Spy magazine, known for its sharp satire and irreverent portraits of public figures, has revived its voice briefly to mark its 40th anniversary by publishing a daily archive article on Substack. The series, launched recently, will run for about a month and features many of the magazine’s signature pieces, with a particular focus on Donald Trump, who was frequently targeted during the publication’s original run from 1986 to 1998.
The lampooning of Trump dates back to the early 1980s when Graydon Carter, later a founding editor of Spy, famously described the then-little-known Manhattan real estate developer as a “short-fingered vulgarian,” a label the magazine repeatedly used. Kurt Andersen, another founding editor, recalled the 1986 New York social scene as dominated by “loud voices,” with Trump standing out for his ostentatious style and brash demeanor. Over the years, Spy’s coverage of Trump was marked by a mix of humor and tenacious fact-checking, often delving into his personal claims and public persona.
The magazine’s editorial approach combined satire with serious journalism. Despite its often biting tone, Spy had a rigorous fact-checking process supported by a team of five specialists. For example, a 1989 cover story critically examining claims made by Trump about his then-wife Ivana’s athletic background involved direct verification with Czech ski authorities, disproving her purported Olympic involvement. Such reporting elicited strong reactions from Trump, including threats of litigation and unusual responses like sending annotated pages back to the magazine with handwritten warnings from his legal team.
Spy’s irreverence extended beyond Trump. It also targeted other prominent figures of the era, including hotelier Leona Helmsley, former Secretary of State Henry Kissinger, and leadership at The New York Times. Publisher Tom Phillips described the magazine’s mission as puncturing inflated egos without hesitation. The publication even conducted stunts such as naming Trump “America’s cheapest zillionaire” after he redeemed a payment of just 13 cents.
Though Trump never followed through on legal threats, his antagonism toward the magazine—and particularly Carter, who later edited Vanity Fair—persisted. In 2015, shortly before launching his presidential campaign, Trump mocked Carter on social media, disputing the “short fingers” jab with a circled magazine advertisement.
When asked whether Spy would maintain its boldness against Trump’s current combative stance toward media, Andersen suggested it likely would. He noted that even under threat of lawsuits, the magazine persisted in its critique, emphasizing that such intimidation attempts never escalated into actual prosecutions.
The anniversary project has reassembled much of the original Spy team, including writers Bruce Handy and George Kalogerakis, who have embraced the opportunity to revisit and comment on the magazine’s most notable stories. Andersen expressed hope that the revived platform might provoke a reaction from Trump or his representatives, underscoring the magazine’s enduring commitment to its provocateur spirit.