‘Surreal’: RTA chair meets with Pope Leo at Vatican, talks AI and White Sox

Regional Transportation Authority Chairman Kirk Dillard is used to extreme experiences, from managing a transit funding crisis to visiting former Illinois Senate colleague Barack Obama in the White House.

On Wednesday, Dillard upped the ante, meeting Chicago-area native Pope Leo XIV at the Vatican.

“He was delightful, and aside from being the pope, he is an original, nice person who has a sense of humor,” Dillard recounted.

Dillard’s opportunity arose through a friend connected with the pope who assembled an informal delegation of visitors from Illinois and other states.

Dillard, a Hinsdale resident, shook the hand of the pope, a native of South suburban Dolton, and conversed briefly.

“We talked about how government officials need to be very careful” with artificial intelligence, Dillard said. “He’s not against AI … but he has clearly has issues with the use of AI, especially when come to human relations.”

On May 25, Pope Leo issued a letter on AI, saying it’s not “inherently evil” but technology is never neutral because it takes on the characteristics of those who devise it. He urged that AI be regulated to work “for the common good.”

The chat also diverted to sports and it’s clear the pontiff still follows “his beloved White Sox,” said Dillard, a Chicago Cubs fan. “We smiled because the White Sox actually have a better record than the Cubs.”

The contingent included state Treasurer Michael Frerichs and state Rep. Kam Buckner.

Dillard noted that just days after Chicago Bears football stadium legislation fell apart in the Illinois House May 31, “lead negotiator Kam Buckner was in the Vatican.”

Asked if the Chicago Democrat had asked for divine intervention, Dillard said he wasn’t privy to Buckner’s chat with the pontiff.

Buckner, who played on the defensive line for the University of Illinois, presented the pope with a Fighting Illini football jersey.

“I played defensive line, but I wouldn’t want to be in front of him,” the pontiff joked after being gifted the “Leo 14” jersey in St. Peter’s Square.

Frerichs gave the pope a $8.65 check from a former PayPal account in Illinois and a commemorative Lincoln coin.

Republican Dillard cosponsored legislation with Obama when they served in the state Senate. The relationship led to a White House reunion, but despite that experience Dillard admitted to some nerves on Tuesday night in Rome.

“I told my wife, ‘This is one meeting I can’t be late for,” said Dillard who gave Leo an RTA shirt depicting the Red Line’s 35th Street Station next to Guaranteed Rate Field with White Sox insignia.

“The man’s schedule is amazing,” Dillard said, noting the pope was juggling scholarly research, his own spiritual journey, leading the Catholic church, as well as celebrating Mass in St. Peter's Basilica for crowds and holding public audiences.

Also memorable was Leo’s multilingual fluency. During Mass Wednesday, the pope effortlessly switched languages to reach as many people as possible at the service, the RTA chief recalled.

Dillard, who is not Catholic but is “a person of faith,” is still processing a “surreal” experience.

“You kind of pinch yourself,” he said.

· Daily Herald staff writer Christopher Placek contributed to this report.