Obama Wants to Meet Pope Leo XIV — And He May Get There Before Trump
The former president's Catholic roots run deeper than most people know. His career began in Chicago parishes funded by the bishops — the same city that formed the pope.
Dear friends —
On Valentine’s Day, Barack Obama sat down with progressive podcaster Brian Tyler Cohen for a nearly fifty-minute interview that covered everything from Trump’s racist AI-generated video depicting the Obamas as apes to the 2028 election. But it was the final question of the night that stopped me cold. Cohen asked Obama who he most wanted to meet.
The 44th president didn’t hesitate. He wants to meet Pope Leo XIV.
What most people don’t know — and what makes this connection even richer — is that Obama’s entire career began in the arms of the Catholic Church.
Today’s subscriber-only essay tells the full story of Barack Obama’s Catholic formation — the bishops’ grants that funded his first job, the rectory where he kept his office, the priests who mentored him, and the cardinal whose “seamless garment” theology shaped how Obama sees the world to this day. It is a story that leads directly to the South Side of Chicago — the same South Side that formed the man who now sits on the Chair of Peter.
And now, sources close to both parties tell me that the Holy See and Obama’s entourage have been in talks about making that meeting happen. As Donald Trump remains one of the only major world leaders on Earth who has not even spoken to Pope Leo XIV, Obama may well meet our pope before the sitting president does. This essay explains why that would be fitting — and why it would be profoundly Catholic.
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“I’ll be honest with you, being president or even being an ex-president, I can kind of meet everybody,” Obama said with his trademark half-grin. “So I’ve met a lot of folks.” But the new pope — the first American pope, the kid from Chicago’s South Side, the White Sox fan — that’s the man Barack Obama wants to sit down with.
Of course he does. This is a Chicago story.
Two South Siders
Barack Obama and Robert Francis Prevost — now Pope Leo XIV — are both products of Chicago, a city that has shaped more of American Catholicism than any place outside of Rome.
They both experienced the same steel mills, the same parish steeples, the same lake-effect winters. And they both carry the imprint of a Church that taught them faith is something you do with your hands, not just your heart.
What most people don’t know — and what makes this connection even richer — is that Obama’s entire career began in the arms of the Catholic Church.
