The Supreme Court on Tuesday signaled it may send a Chicago political scion’s appeal of his conviction for lying to regulators back to a lower court to flesh out the difference between false and misleading statements. 

Patrick Daley Thompson, a member of Chicago’s most famous political dynasty, was convicted in 2022 of lying to regulators about the amount he borrowed from a now-defunct bank. He already completed a four-month prison sentence.

Thompson insisted to a loan servicer’s customer service line that he borrowed $110,000 not the more than $269,000, including interest, the servicer said he owed. But the former alderman neglected to mention two other loans, totaling $109,000.

He settled the debt with the Federal Deposit Insurance Corporation by agreeing to pay the principal of $219,000 but not the interest. He was later charged with violating a federal anti-corruption law that bars making false statements to influence certain government agencies and financial institutions.

Thompson’s appeal turns on whether that law also prohibits making statements that are “misleading but not false.” It’s the high court’s latest case weighing how federal authorities prosecute local politicians.

Chris Gair, Thompson’s attorney, argued Tuesday that a falsity is an untruth about an objective fact while a misleading statement depends on what a reasonable person hears. 

“Many, many false statements are misleading, and many misleading statements are false,” Gair said. “But that does not mean they are synonyms.”

He asked the justices to kick the case back to lower courts to decide into which bucket Thompson’s statements fall in addition to finding that the lower courts “erroneously” held that the statute punishes both false and misleading statements. 

The justices spent most of their questioning contemplating what marks the difference between false and misleading statements. Justice Ketanji Brown Jackson suggested that, even if the court agrees with Thompson’s view of the statute, it might not change the former alderman’s situation. 

“Based on what you’ve said you believe a false statement is, I guess I don’t understand how that helps your client in this case,” Jackson said. “Because the amount of money that he borrowed or that he owed, I would think, is a knowable fact with one correct answer.”

Justice Amy Coney Barrett reached a similar conclusion, suggesting she sees Thompson’s situation as “different” because his statement “sounds an awful lot like all I owe is $110,000.”

The Justice Department said a statement is false if it conveys an untrue message to the listener in context, even if the exact words used could carry another meaning if “considered in a vacuum.” 

“Our position in this case is not that false encompasses anything that might be characterized as misleading or any failure to disclose pertinent information,” said Caroline Flynn, the attorney representing the government. “It is that a statement is untrue if it states only a portion of the truth on the subject it addresses in a context where the statement would be taken as both accurate and complete.”

The justices noted a jury found Thompson guilty of making false statements but was not instructed to consider whether his remarks instead were misleading. 

Gair argued that no reasonable jury would find Thompson’s statements false if presented with the option that they were instead misleading a tough row to hoe, Justice Neil Gorsuch remarked. Flynn argued the opposite. 

However, Gorsuch noted the case wasn’t taken up by the high court so the justices could decide whether a reasonable juror would find the defendant made a false statement. 

“We took it to resolve whether the statute allows the government to pursue a theory of misleading rather than false,” he said. 

Justice Elena Kagan suggested it might be beneficial for the justices to provide guidance to other courts on the difference between false and misleading when issuing their decision. 

She described a hypothetical scenario where a doctor, in attempting to convince a patient to have a surgery, says he’s done 100 of those surgeries but neglects to mention that 99 of the patients died. 

“100 of these surgeries true statement, correct?” she said, drawing laughter from the gallery.

“So, that’s the kind of thing where there really is a gap between a false statement and the misleading statement,” she added. 

Thompson attended the argument Tuesday. He is the grandson of Chicago’s late Mayor Richard J. Daley (D) and the nephew of former Mayor Richard M. Daley (D), the city’s two longest-serving mayors. William Daley, Thompson’s uncle, also served as chief of staff to former President Obama.

The former alderman was also found guilty of filing false income tax returns, but those convictions are not before the justices.

If the justices rule in Thompson’s favor, it could mark a second case in as many years where the Supreme Court found federal prosecutors overstepped while cracking down on local politicians.

The justices last summer narrowed the scope of what can be considered an illegal gratuity to a government official. That case involved former Portage, Ind., Mayor James Snyder (R), who in 2014 received a $13,000 check for consulting services from a garbage truck company after the town awarded lucrative contracts to the company the previous year.

The decision sparked concern among watchdog groups and legal experts who noted Justices Clarence Thomas and Samuel Alito have been scrutinized for accepting lavish gifts and hospitality from wealthy benefactors.

The ruling was also expected to make it tougher to prosecute public officials for accepting bribes. It forced federal prosecutors to reassess bribery charges against another Chicago politician, former Illinois House Speaker Mike Madigan (D), who is on trial now, and could play a role in former Sen. Bob Menendez’s (D-N.J.) appeal of his bribery conviction. 

A decision in Thompson’s case is expected this summer.