In the 1990s, the Pritzker family, led by brothers Jay and Robert Pritzker, engaged in a bitter feud with Donald Trump over their joint venture, the Grand Hyatt Hotel in New York City, a project that marked Trump’s first major real estate triumph in 1979. The Pritzkers, who owned Hyatt Corporation, were equal partners with Trump but managed the hotel under a contract that restricted them from operating other convention hotels in New York. By the early 1990s, as Trump faced financial turmoil with $900 million in personally guaranteed debt, the Pritzkers allegedly sought to exploit his vulnerability. Trump’s 1993 lawsuit against Jay Pritzker accused the family of using questionable accounting practices and unauthorized payments to siphon millions from the Grand Hyatt, aiming to force Trump out of the partnership and free Hyatt to pursue other New York ventures. The lawsuit, which demanded $500 million in damages, claimed these actions were part of a deliberate scheme to bankrupt Trump and reclaim full control of the property their father, A.N. Pritzker, had helped develop with Trump.

The roots of Jay Pritzker’s public criticisms of Trump, which have been echoed by his nephew J.B. Pritzker in recent years, appear to stem from this contentious history, compounded by what some describe as a deeper, almost tribal animosity. Posts on X and various reports suggest the Pritzkers harbored resentment toward Trump, not only for his financial resilience but also for his brash, outsider persona that clashed with their established Chicago elite status. Jay Pritzker’s defense against Trump’s lawsuit dismissed the allegations as a diversion, but the legal battle—coupled with Trump’s ability to navigate his financial straits through deals like the one facilitated by Wilbur Ross—thwarted the Pritzkers’ alleged efforts to oust him. This failure reportedly fueled a lasting grudge, with J.B. Pritzker later taking jabs at Trump’s wealth and competence, famously calling him “rich in only one thing: stupidity” at the 2024 Democratic National Convention. Some interpret this as a continuation of a family vendetta, rooted in the 1990s clash and amplified by cultural and political differences between the Chicago-based Pritzkers and the New York-centric Trump.

Now, as President of the United States, Trump is positioned to “get even” with the Pritzkers, particularly J.B. Pritzker, whose high-profile opposition has made him a visible target. The 1990s feud, where Trump accused the Pritzkers of racketeering and financial sabotage, left a lasting mark, with Trump’s 2025 comments calling J.B. “the worst governor in the country” signaling an ongoing personal and political rivalry. Posts on X speculate that Trump’s second term could see him leverage federal authority—such as immigration enforcement or economic policy—to challenge J.B. Pritzker’s influence in Illinois, a state Trump has criticized alongside Chicago’s leadership. The Pritzkers’ wealth and political clout, built on the Hyatt empire and connections to Democratic causes, contrast with Trump’s narrative of self-made success, setting the stage for a potential escalation of this decades-long conflict between two billionaire dynasties, with Trump now wielding the power of the presidency to settle old scores.