Family Feud: Donald Trump and the Pritzkers

During Joe Biden’s administration, Donald Trump denounced what he claimed to be “lawfare,” the weaponization of the law by the elites to throttle political dissent. Now, Trump wants to use the justice system to retaliate against his enemies and stifle political dissent. Having narrowly avoided jail himself, Trump continues to threaten his enemies with imprisonment. In a Truth Social post the other day, he mused that Illinois Governor JB Pritzker and Chicago Mayor Brandon Johnson would “land in jail.” Pritzker is the scion of a billionaire hotel baron family of the Hyatt chain, with whom Trump has historically enjoyed a fractious relationship.

Will Pritzker have to share a cell with Jim Comey? With Adam Schiff? Or maybe John Bolton? Is this America?

Trump’s post came a day after Texas National Guard troops arrived in Illinois, despite fierce opposition from Democrats. The president has been vocally advocating for sending troops to Chicago for weeks. He has described Chicago as a “killing field,” a “hell hole,” and “the murder capital of the world,” and has said he will deploy National Guard troops to “solve the crime problem fast.” White House spokesperson Abigail Jackson stated that “JB Pritzker and Brandon Johnson have blood on their hands” and accused them of “standing idly by while innocent Americans fall victim to violent crime repeatedly.” Chicago’s violent crime rate decreased by 11 percent last year compared to 2023 levels and is about half of what it was in the years before the COVID-19 pandemic. According to BBC Verify’s analysis of FBI data, the city ranks near the bottom among U.S. cities with populations over 500,000, placing 29th out of 37. While a federal district court halted Trump’s Chicago troop surge, the Supreme Court agreed to hear the case on Friday.

The courts have blocked Trump from deploying troops in Chicago and nearby areas. However, they have approved the administration’s request to keep the National Guard under federal control in Illinois instead of sending them back to their home states.

The White House statement did not answer questions about what crimes the president thinks Johnson and Pritzker committed, or whether the White House plans to have federal agents arrest them.

This isn’t the first time Trump, 79, has dealt with the Pritzker family. Animosity between the Trumps and the Pritzkers runs deep. In 1977, Trump reached out to the bankruptcy trustees of the Penn Central Railroad to buy an option on the 1,800-room Commodore Hotel next to Grand Central Station. The Pritzker family was a clan of seasoned billionaire hotel developers who successfully managed 777 hotels in 54 countries. During his first major real estate deal, Trump convinced the Pritzkers that he was a valuable partner for a new 1,400-room hotel called the Grand Hyatt on the site of the old Commodore. The Grand Hyatt would be the first hotel in New York City owned by the Pritzker family, who financed the project. This deal put Trump on the map. The Pritzkers invested the money, making Trump a 50 percent owner of a multimillion-dollar property without contributing a dime. 

The relationship between Trump and the Pritzkers was fractious from the start. Over the years, the parties became embroiled in at least three arbitrations. The results of the arbitrations are kept from the public by court order, so we lack details. We know that Trump accused the Pritzkers of negligent property management and failing to maximize revenue. The strained relationship festered, eventually erupting into full-scale litigation. In 1993, Trump, seeking triple damages, sued the Pritzkers in federal court under the Racketeer Influenced and Corrupt Organizations (RICO) Act. He alleged that the Pritzkers had “systematically looted tens of millions of dollars from the Grand Hyatt through theft, fraud, waste, and mismanagement.” The Pritzkers vehemently denied these accusations and quickly moved to dismiss. Their motion was never resolved because Trump eventually dropped the case. The suggestion that such seasoned and successful hotel operators had done a “horrible job” defied credulity

Trump was a big supporter of RICO suits. Prominent law firms, well-known accounting firms, and even Fortune 500 companies have all been named in complaints alleging civil RICO violations. Most of these claims are dismissed by courts as without merit. RICO remains a powerful legal tool because the stakes are intimidating. Lose the case, and you face significant damages along with the winning side’s legal fees, which can be substantial. Trump told the New York Post that he filed the RICO case against the Pritzkers because “the rich have a very low threshold for pain,” and “I don’t like being pushed around, and now they’re beginning to learn it.” 

Trump claimed that the Pritzkers aimed to force him out of the partnership. This covered Trump’s real goal of getting money from the clan. 

In 1994, the Pritzkers sued Trump in federal court for violating their partnership agreement by failing to stay solvent, using his stake in the hotel as collateral for bank loans without the Pritzkers’ approval, and refusing to pay his agreed-upon share of necessary renovation costs. Trump defended his dealings with the banks, saying, “Every ‘i was dotted, and every ‘t’ was crossed.” He described the renovations proposed by the Pritzkers as “irrational and foolish.” In an interview with the New York Times on May 29, 1994, he stated of the Pritzkers, “They’re spending money like drunken sailors.” 

Telling his story to the press, Trump said of the firestorm, “I see this ending when they give up the hotel management. This is a fractured relationship. I think Hyatt has done a horrible job in the management of the Grand Hyatt, and I want them out. That is the goal of my lawsuit.” But the Pritzkers had enough of Trump’s lawsuits and wanted a divorce. The “fractured” 17-year relationship ended in 1996 when the Pritzkers bought out Trump for $140 million.

When Trump was interviewed at a meeting of the Economic Club in Washington in December 2014, he did not criticize the Pritzkers and called the Grand Hyatt “very, very successful.” Sure, it was “successful”—for him. He had contributed practically nothing to the hotel’s construction or maintenance costs, and by intimidating his partners with a failed racketeering charge, he walked away with a cool $140 million. 

And, as it happens, Penny Pritzker, JB’s sister and the former Commerce Secretary, is Senior Fellow of the Harvard Corporation, the board responsible for the university’s operations. Harvard is a Trump bête noire, one of the most visible liberal institutions on Trump’s enemies’ list.

If you don’t think Trump remembers his grudges, ask Jim Comey, Letitia James, or John Bolton. Now Trump is back at the Pritzkers again. Asked during a White House event if he had urged the Justice Department to investigate potential charges against Pritzker and Mayor Johnson, he reaffirmed his statement from his Truth Social post.

“I’ve seen the law. And when you have a group of people where the police call off the safety for ICE officials, I’ve understood that, and I’ve read it today in numerous journals, that that’s illegal,” Trump said. I would really like to know what journals he was referring to.

Governor Pritzker, 60, a teenager when the feud with Trump began, responded to the president’s Truth Social post by writing on X, “I will not back down.”

“Trump is now calling for the arrest of elected representatives checking his power,” he wrote. “What else is left on the path to full-blown authoritarianism?”

Later, Pritzker told reporters that Trump is “a coward.” “He likes to pretend to be a tough guy,” Pritzker said of the president. “Come and get me.”

Illinois has, of course, sued to prevent the White House from deploying federalized troops to Chicago. April Perry, a Biden-appointed judge who graduated from the Pritzker School of Law at Northwestern University, held a hearing and issued a preliminary injunction, which currently blocks the deployment. The judge said the deployment was “likely to lead to civil unrest.” Trump is certain to appeal her ruling. Attorneys for the government argued that the courts should be “highly deferential” when reviewing a president’s judgment, stating that it is within the scope of the authority granted to the executive branch by the Constitution and statutes. Mayor Johnson called the ruling “a win for the people of Chicago and the rule of law.” But if the Supreme Court’s past rulings are any indication, they’re likely to uphold the troop surge while they wait to hold oral arguments.

Trump previously argued that deploying the National Guard was necessary to “protect federal assets and personnel” and prevent “attacks on law enforcement.”

He initially deployed the National Guard to Los Angeles despite California Governor Gavin Newsom’s objections, following protests in response to immigration raids. Then, the president ordered the National Guard to the streets of Washington, D.C., framing it as a move to combat crime.

The administration also tried to send federalized National Guard troops from California to Portland, Oregon. Still, a judge issued a temporary restraining order to stop the move while the case is considered in court. A Pentagon spokesperson said the troops would have worked to “support U.S. Immigration and Customs Enforcement and other federal personnel performing official duties, including the enforcement of federal law, and to protect federal property.”

In Chicago, a frequent target of the president, Mayor Johnson signed an executive order on Monday to block immigration agents from using city property during their operations in Chicago.

“We will not tolerate ICE agents violating our residents’ constitutional rights, nor will we allow the federal government to disregard our local authority,” Johnson said in a news release marking the so-called ICE-Free Zone executive order.

Pritzker has emerged as a leading critic of the Trump administration as his state faces the president’s ire, and he is expected to seek the Democratic nomination for president in 2028. Trump has compared Chicago to a “war zone,” and Pritzker said recently on CNN’s “State of the Union” that “they’re just making this up.”

“Then what do they do? They fire tear gas and smoke grenades, and they make it look like it’s a war zone,” Pritzker said, appearing to refer to federal agents. “And they, you know, get people on the ground who are, frankly, incited to want to do something about it, appropriately.”

Recently, Pritzker has also said that he believes that Trump should be removed from office.

“There is something genuinely wrong with this man, and the 25th Amendment ought to be invoked,” he said, referring to a process for removing the president from office.

House Speaker Mike Johnson did not say whether he believed Mayor Johnson and Gov. Pritzker should be jailed when asked by NBC News about Trump’s post.

“Should they be in prison? Should the mayor of Chicago and the governor of Illinois be in prison?” Johnson responded. “I’m not the attorney general. I’m the speaker of the House, and I’m trying to manage the chaos here. I’m not following the day-to-day on that.”

On Tuesday, Pritzker was asked during an event whether he believed he could be arrested.

“I’m asking any of you to come visit me in the gulag in El Salvador,” Pritzker joked, referring to the horrific prison where the Trump administration has deported some immigrants.

An aside: From a historical perspective, it’s interesting to compare our justice system with that of England, from which we inherited it. In England, the executive branch is essentially a clone of Parliament and is closely tied to it. The Prime Minister and all cabinet members are also members of Parliament. There, it would be unthinkable for Keir Starmer to order the Director of Public Prosecutions to jail his political enemy, Nigel Farage. We have a separation of powers that protects us from authoritarian rule. Yet, Trump violates all presidential norms since Watergate by declaring himself the “chief law enforcement officer” of the nation and blurring the lines between his role and that of Attorney General Pam Bondi in politically charged cases. 

When the framers granted the president significant power under Article II of the Constitution, they were thinking of George Washington, not Donald Trump. We are well on the path to becoming a banana republic.