President Donald Trump and Illinois Governor JB Pritzker have a history of disputes that dates back to the early 1990s, when both were involved in a disagreement over the ownership and management of the Grand Hyatt hotel in New York. At that time, Trump and the Pritzker family each owned half of the property.
The conflict began in 1992 when the Pritzkers, led by JB’s late uncle Jay Pritzker, pushed for an expensive renovation of the hotel. Trump, facing financial difficulties due to his Atlantic City casinos being in Chapter 11 bankruptcy, saw this as an attempt to pressure him at a vulnerable moment. He responded by suing the Pritzkers for civil racketeering, an allegation they denied.
“I called Jay [Pritzker] and said, ‘You’re a bad guy, Jay. I’m going to kick your ass,’” Trump told the Wall Street Journal in 2016.
The dispute ended with a settlement in which Hyatt Corporation bought Trump’s share of the hotel for $140 million. Jay Pritzker died in 1999.
In recent years, tensions between Trump and JB Pritzker have continued on issues such as wealth, immigration, crime, and democracy. Pritzker has publicly questioned Trump’s mental fitness and suggested he has dementia.
Last week, tensions escalated after federal agents from the Department of Homeland Security raided a building on Chicago’s South Shore. The operation resulted in the arrest of 37 people and raised concerns among local officials about tenant rights after some residents, including children, were detained. The incident highlighted ongoing debates about landlord and tenant rights amid increased federal scrutiny.
Following the raid, Trump deployed 300 Illinois National Guard members and 200 Texas troops to Chicago. Pritzker condemned this action as unconstitutional and filed a lawsuit seeking a restraining order. In response to criticism from Pritzker and Chicago Mayor Brandon Johnson regarding immigration enforcement activities, Trump stated that both officials “should be in jail.”
The feud is not limited to JB Pritzker alone. His sister Penny Pritzker has also had conflicts with the Trump administration over claims of antisemitism at Harvard University, where she is a senior fellow on its governing board.
