President Donald Trump is once again targeting one of his favored political foils: former Chicago Mayor Lori Lightfoot. In a fresh round of public remarks, Trump criticized Lightfoot as part of a broader attack on Harvard University, where she now holds a faculty position.
The latest round of insults surfaced as Trump railed against what he described as the “radical left-wing capture” of elite academic institutions. He cited Harvard’s decision to hire both Lightfoot and former New York City Mayor Bill de Blasio as evidence that the university has lost its way—and even went so far as to suggest it should be stripped of federal funding.
“Certainly two of the worst mayors in the history of our country,” Trump said at a recent cabinet-style meeting, singling out the two Democrats. On his social media platform, he escalated his rhetoric, calling Lightfoot a “Radical Left fool” and “evil.”
The criticism is part of a long-running feud between Trump and Lightfoot, who frequently clashed with him during her time as mayor, particularly during the racial justice protests and public health battles of 2020. Trump often used her leadership of Chicago—a city he repeatedly described as crime-ridden and poorly managed—as a stand-in for Democratic governance more broadly.
Lightfoot, for her part, isn’t backing down. While she hasn’t issued a full response to the latest comments, she’s faced similar jabs before and has shown little inclination to stay silent. During her tenure, she regularly pushed back against Trump’s attacks, often accusing him of using Black women in leadership as scapegoats to energize his political base.
Her defenders argue that Trump’s repeated fixation on Lightfoot reflects a deeper discomfort with progressive urban leadership—and plays into a broader pattern of targeting high-profile Black public figures.
With Trump back on the campaign trail and Lightfoot stepping into a new academic chapter, the rivalry shows no signs of cooling off. And if past is prologue, she’s unlikely to take his latest comments sitting down.