A photo of a young Pope Leo, back when he was Fr. Robert Prevost, is getting attention on social media. What does it reveal about how he sees himself?
A photo of a younger Pope Leo XIV, back when he was Fr. Robert Prevost, is getting lots of attention on social media. What does it reveal about how the Holy Father sees himself?
Scott Detrow, co-host of NPR’s All Things Considered, and Daniel Burke, NPR’s Senior Editor of Religion and Spirituality, are working on a forthcoming book called American Pope: Leo XIV's Road from the South Side of Chicago to Vatican City. In the course of their research, the two have come across little-known stories and images from Pope Leo’s earlier life, and one of these has gone viral on social media.
In a post on Substack, Scott Detrow explained the story behind the images:
“American Pope” publishes exactly a month from today. We are marking the final weeks before launch with pictures of Pope Leo XIV we came across over the course of reporting, and the stories behind them.
Some of the images show moments you would expect, such as young Bob Prevost as a student reading a book, but the one getting the most attention shows him holding up a white cloth with simple drawings painted on it.
Detrow explained it with this caption:
Here’s how Pope Leo XIV once told his own story.
When he was prior general of the Augustinians, he participated in an exercise where everyone drew a painting portraying their identity. Father Prevost painted an American Flag, Chicago's Sears Tower, and "CW Sox," along with the Order of Saint Augustine's symbol and a Christmas tree.
What the symbols mean
The image is a fascinating glimpse into how the future pope saw himself. The symbol of the Augustinian Order makes perfect sense, as God called him to a vocation with this order. The American flag is a natural choice as well, given his All-American upbringing in a Midwestern suburb.
Another two of the images might seem unexpected, but are immediately recognizable to his fellow Chicagoans.
“CW Sox” stands for his favorite baseball team, the Chicago White Sox. He attended two of the team’s World Series games in 2005, and since his papal election, the Sox have celebrated their most famous fan with a mural and theme night, among other things.
But why The Sears Tower? You have to understand what this building means to Chicagoans.
The Sears Tower (now officially named the Willis Tower, although you’ll never catch a Chicagoan calling it that) was the tallest building in the world from 1973 until 1998. It’s still the tallest building in Chicago, and with its jet black exterior and two white antennas, it’s a landmark impossible to miss even from many miles away.
From early childhood, Chicagoland children learn to identify it every time they drive within sight of the city, and it stands as a beloved icon of the city’s culture and strength — something that immediately screams “Chicago.” Construction on the tower was completed when Pope Leo was 17, so it was likely a memorable event during his teen years, and his choice to include it reveals how deep and close to his heart lie his Chicago roots.
And as for the last image, a Christmas tree? This one gives insight into his enjoyment of Christmas — the birth of Our Lord and a time of warmth, connection with family, and love.
His love for Christmas is notable even this early in his pontificate. For his first Christmas as pope, Pope Leo XIV revived a tradition of celebrating Christmas Day Mass in St. Peter's Basilica, something no pope had done since 1994. In his homily at that Mass, he called Christmas “a feast par excellence of music and song” that “causes us to break forth into songs of joy.”
If the images Detrow has been sharing on social media are any indication, American Pope promises to be a fascinating book, filled with all kinds of new information about Pope Leo XIV. The book will be released on October 6, 2026, and in the meantime we can enjoy learning more about Leo from Detrow’s posts about his research on social media.












