Pope Leo swapping skullcap for White Sox cap at Vatican sends Internet into frenzy: 'That's a pontiFLEX!

Pope Leo wore a Chicago White Sox baseball cap after a newlywed couple from Massachusetts gave it to him during a general audience
PUBLISHED JUN 13, 2025
Pope Leo XIV, a Chicago native and the first American pontiff, wore a White Sox baseball cap during a general audience at the Vatican on June 11 (@whitesox/X)
Pope Leo XIV, a Chicago native and the first American pontiff, wore a White Sox baseball cap during a general audience at the Vatican on June 11 (@whitesox/X)

VATICAN CITY: Pope Leo XIV may lead the global Catholic Church from the historic heart of the Vatican, but he hasn’t forgotten his Chicago roots especially not when it comes to baseball.

On Wednesday, June 11, the newly appointed pontiff stunned onlookers in St Peter’s Square when he arrived to greet newlyweds wearing a traditional white cassock topped with a bold black-and-white Chicago White Sox baseball cap, reports Unilad.



 

Massachusetts newlyweds share how viral moment with Pope Leo came about

Pope Leo's break from protocol has gone viral and the pair newlyweds who gave it to him are proud Red Sox fans from Haverhill, Massachusetts. "He was so down to earth that you really can't rationalize who you're standing with," Gary DeStefano recalled to CBS News. 

Haverhill newlyweds Kelly and Gary DeStefano topped their dream honeymoon with a once-in-a-lifetime photo op alongside Pope Leo who is now arguably baseball’s most famous White Sox fan.

"This is exactly the way he left it," Kelly told the outlet. "And he proudly puts it on, and he jokes with us, 'You're going to get in trouble, but I'm not!' Because we're Red Sox fans!" she shared, recalling the Pope’s playful moment with them.

There's more to the story as Kelly shared how it all came to be. The couple had always dreamed of catching a glimpse of the pope on their honeymoon. When Pope Francis died just a month before their wedding, they were heartbroken. 



 

"Then it was the first American pope and then it was a mission. My cousin Paul Breen came to our wedding and said, 'You don't know how hard it was to find these White Sox hats. They don't sell them in Massachusetts!' If we would be in the large crowd he said, 'Put them on, maybe the pope would see you.' We were lucky enough to get tickets and seating for the sposi novelli and personally got to meet the pope," Kelly shared. 

Now the husband and wife say the White Sox hat is going to be stored in a case and kept for the grandchildren. 

"If one thing brings the country together it's sports. Whether we're Red Sox fans, he's a Chicago fan, by showing him that hat. He laughed. He has a difficult job. If you bring laughter into somebody's life that little bit even in his position, what more could you ask for? We're very grateful," said Gary. 

Internet reacts to Pope Leo's viral White Sox cap moment

The unexpected fashion statement lit up social media and delighted netizens, many of whom had no idea the new pope, born Robert Prevost, was such a diehard White Sox supporter.

Pope Leo XIV holds an audience for participants in the Jubilee of Eastern Churches at the Paul VI Hall on May 14, 2025 in Vatican City, Vatican. Today, pilgrims participating in the Jubilee of the Eastern Churches attended an audience with Pope Leo XIV, followed by a celebration of the Divine Liturgy in the Byzantine Rite at St. Peter's Basilica. Eastern Catholics are in full communion with the pope but are not part of the Latin Church. (Photo by Vatican Media via Vatican Pool/Getty Images)
Pope Leo XIV holds an audience for participants in the Jubilee of Eastern Churches at the Paul VI Hall on May 14, 2025, in Vatican City (Vatican Media via Vatican Pool/Getty Images)

An X (formerly Twitter) user wrote, “Not Catholic but @Pontifex has been dropping banger after banger here. Would tailgate w/ him in a heartbeat. My lost chicago friends might try to push him on a blue hat and an old style but would settle for malört at the communion table. bring brats.”



 

Another couldn't help but crack a pun as they wrote, "That’s a pontiFLEX!"



 

A person enthusiastically wrote, “That’s MY POPE.”



 

Needless to say, baseball fans asked the all important question, with one writing, "Now when is his ceremonial first pitch?"



 

One joked, “Pope being for the less fortunate indeed,” while another quipped, “Good to see the Pope supporting the poorest and most downtrodden among us.” An individual echoed, “Sadly, he could start for the White Sox right now. They need all the help they can get… 2nd worst record in baseball.”



 



 



 

Others already saw historic potential in his flair, as one wrote, “Should Leo XIV ever be made a saint, that hat will properly be a relic and could be used to sanctify a Church."



 

Another thought the whole thing was very "humanizing" as they said, "That is actually really cool that the Pope is a fanboy for baseball. Very humanizing!!"



 

Pope Leo's love for baseball

Pope Leo's election in early May as the first American pope already caused a stir in religious and cultural circles. Born in Chicago and raised in a sports-loving household, the 69-year-old has quickly become a relatable figure even to those outside the Catholic faith.

Pope Leo XIV meets with representatives and pilgrims of the Eastern Catholic Churches at the Nervi Hall, on May 14, 2025 in Vatican City, Vatican. Today, pilgrims participating in the Jubilee of the Eastern Churches attended an audience with Pope Leo XIV, followed by a celebration of the Divine Liturgy in the Byzantine Rite at St. Peter's Basilica. Eastern Catholics are in full communion with the pope but are not part of the Latin Church. (Photo by Vatican Media/Vatican Pool - Corbis/Getty Images)
Pope Leo XIV meets with representatives and pilgrims of the Eastern Catholic Churches at the Nervi Hall, on May 14, 2025, in Vatican City (Vatican Media/Vatican Pool - Corbis/Getty Images)

Despite brief attempts by Chicago Cubs fans to lay claim to him, the pontiff’s brother, John Prevost, quickly shut down the rumors. “He was never, ever a Cubs fan. Our mother was a Cubs fan. Our dad liked the Cardinals. But Robert? Always Sox. That was never up for debate,” he told local media. 

In fact, Pope Leo was actually at Game 1 of the 2005 World Series, a historic sweep for the White Sox, which confirms his enduring baseball allegiance. 

This article contains remarks made on the Internet by individual people and organizations. MEAWW cannot confirm them independently and does not support claims or opinions being made online.

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