this your first Conclave? So I was there

for Francis.

You were, I forgot that.

But certainly, you know, It was different.

I think what was so striking is after people realized that it was an American, it was kind of a weird vibe there.

You were there, right, in Rome, and people really didn't know how to take it.

They knew that You know, OK, this is an American.

Why is that? What's going on here? Is it just Leo? Is it the fact that the world is in a different place? Why why has he become, you know, this guy become really the central moral figure? And so, yeah, we're day.

Daniel, can you tell us the story about when he got a toy truck?

Sure, yeah.

So he got a toy truck for Christmas.

He loves trucks.

One of his neighbors was a truck driver, and he would just go out into the front yard and just look at this truck.

It became like a lifelong fascination with cars and trucks and all kinds of things.

So he was really excited to get this truck on Christmas.

And the church was often a target of attacks.

Why does he end up there for school?

school?Yeah.

The short answer is they recruit him.

Uh, he is a devout young boy.

Two of his brothers go to an Augustinian high school where his mom also sometimes volunteers as a librarian, so they know him, and he knows a little bit about the Augustinian order because his froth- father would occasionally bring over a Spanish friar, uh, and they-- to family dinners, and they would kind of talk about the church and the order and missionary work and things like that.

So he decides to go to this high school, as you mentioned, in Holland, Michigan, and the draw for the Order of St. Augustine is that it is so isolated.

It's physically isolated from its surroundings.

Well, I think, Daniel, that's a good way, I'll, I'll, I'll flip it over to you, but that's a good way to think about the, the kind of listening first approach and the, the kind of less hierarchical approach that we have seen Pope Leo embrace over the years.

And I'm, and I'm gonna go to Daniel and, but Scott, please, both of you kind of tell us this story of Pope Leo and how it, how this experience shaped him.

Sure.

So he, he learns about the Augustinian order pretty early in his life.

His father befriends, um, a Spanish friar.

They're called friars, which is brother in, in French.

Um, and he brings him to the, the Prevost house, and he, they have dinner, so he learns about the Augustinians and their missions and their orders.

Two of his brothers go to an Augustinian high school, so he knows about the order.

Mm-hmm.

And in the very religious family...

Yeah, I think it's fair to say that the church was the center of their lives.

They organized their activity, their daily life around the church, around the church schedule.

They went to mass almost every day, if not every day.

They said the rosary every day in the living room.

They had, you know... prayers before meals, but it wasn't just that.

They were a really active family that social justice actually meant a lot to them.

The priest from Peru who he meets when he's young and eventually works with later.

Hey, Daniel, in the book you include a quote from a, a St. Augustine sermon, uh, that in part says, "A lame man limping along the road goes further than a sprinter running off it." What does that tell us about Pope Leo and his journey to becoming pope?

Yeah.

So that's a quote from St. Augustine, as you said.

He introduced himself to the world on May 8th, 2025 as a son of St. Augustine, and he has been part of the Order of St. Augustine basically since he was in high school.

And so this is a really, really important figure to him, and he's quoted that passage.

I found the speeches that he gave when he was head of the Augustinian Order.

He would quote that passage all the time.

And I think the, the best way to say is that he was a little slow to grasp how serious the problem was.

Daniel, how did that approach align with where the Catholic Church was? was or where it wanted to go as he ascended to the papacy.

Yeah.

So I think with the Advent of Vatican II, which is this big church meeting in the mid-1960s, what it does is, what it tries to do is take some of the power from the hierarchy and give it to the laity, give it to laypeople.

It wound up developing a little bit more in Latin America than in the United States, which is interesting.

So in 1985, Robert Prevost is in Rome.

He's studying to get a degree in canon law.

But there's this accident in Peru where Augustinians have started a mission.

And what drew him to that order specifically?

Describe what it was like.

Oh, it was unbelievable.

Uh, I remember Scott was actually making the call on air, uh, announcing that the Pope was from Chicago of all places.

You just heard this wave of energy move through the crowd.

And once we got over the shock of there being an American pope in the first place, we quickly realized that there was a, a really important story to tell about who exactly this man was, Robert Prevost, who was kind of off a lot of people's radar.

You know, he was a, a high-ranking church official, but he wasn't really well known to that many people.

Yeah.

He went to grade school there.

And, you know, you're right that they were encouraged to date and they could like, I don't think he ever did, but like they were around and with other students and, um, Did that shake him up at all? What did you learn about that time of his life?

yeah i think it was a little bit of a culture shock moving from this high school seminary in michigan to a major east coast university and villanova wasn't as big at the time it was honestly mostly a commuter college from catholic kids from the northeast but it was still a very very different experience he could you know attend a lecture by margaret mead the favorite famous anthropologist he could see bruce springsteen who was like a rising rock star in philadelphia um He could do all of these things.

What's fascinating is that if you go through the high school newspapers from St. Augustine High School, he's all over the place.

He's like there three or four times in a page.

I look through every newspaper, Villanova, all four years and he's nowhere.

He disappears from the social scene in a big way.

I asked a lot of friends about that and I think this is when he started to get serious about the priesthood.

Yeah, again, like kind of quickly, if you can't like what what is what he gets there, like what is what's the approach? What do we see about him as missionary? Like what is his style?

Daniel, for you, I mean, d- can you have a Pope Leo without, uh, Pope Francis being the predecessor?

I don't think so.

And I, I also think that Pope Francis's funeral, which was nine days before Pope Leo, the conclave that elected Pope Leo, I think it had a profound effect on Catholic leaders in Rome.

To see so many people turn out in Rome to celebrate the life of Pope Francis made a deep impression on the cardinals who would then vote to elect his successor.

And we talk about all of the ways in which Pope Francis kind of elevated Robert Prevost throughout the Church, and those, those were small ways, like meetings that they would have together.

It was kind of like pope school, this is how you run a, an extraordinary complex organization.

But also, he elevated him in formal ways, like making him the highest rank of cardinals within the College of Cardinals.

Of course, Pope Leo is known as the first American pope, but it sounds like time outside of the States really helped to shape much of his work.

A, in many ways, purely American story, but so much of his adult life was informed by living in Peru.

That's right.

He goes to Peru in his early 30s.

It was kind of a, a surprise to him.

He had thought about missionary life a little bit as a teenager in high school, but he was on the path to elevate in, in Rome.

You know, he was studying in one of the most prestigious universities.

He was studying canon law.

Is he a moderate? Is he a progressive? Based on your reporting, how useful are those labels, if at all, in understanding who he really is?

In Prevost, Pope Leo grew up, obviously, in Chicago, attended Villanova, in many ways, purely American story, but so much of his adult life was informed by living in Peru.

That's right.

He goes to Peru in his early 30s.

It was kind of a surprise to him.

He had thought about missionary life a little bit as a teenager in high school, but he was on the path to elevate him in Rome.

He was studying in one of the most prestigious universities.

He was studying canon law.

Is he a moderate? Is he a progressive? Based on your reporting, how useful are those labels, if at all, in understanding who he really is?

You can only take someone's word for it.

Mm.

It's a very interesting point because the, the, the reason the crisis ap- even in that regard, like, what you're saying absolutely applies in many cases, but with the crisis apparition, fun- the reason why it's so interesting a- a- and sets itself apart from many phenomenon is because in, in, in some sense you can, quote-unquote, "prove it" because- Uh, you can at least prove the coincidence.

The p the...

It's pretty...

It's, it's not really debated that the coincidence occurs.

It's just the explanation of it.

There's so many

But I'm curious, one, how's it working with your wife? And two, how bullish are you on the local newsletter scene?

I love my wife to death.

It's amazing working with her.

She's really the, the mind behind it.

I do all the business side of stuff, and really early on taught her how to do Beehiiv.

Uh, it's all built on Beehiiv, and so, you know, she knew Beehiiv vicariously through me and not as a op- operator herself.

That's obviously since changed.

I'm curious, you know, w- what you see, you know, in the space in, you know, uh, in media and what that means for what you're doing next.

Uh, Daniel Burke, tax partner at, uh, Pitcher Partners, can you explain capital gains tax like we're 12?

Good morning, Ross.

Good morning, Russell.

Yeah, um, great to be here again.

Um, yeah, happy to give you the 101 on capital gains tax.

So largely, capital gains tax is taxing the growth in value, uh, of an asset from the cost that you originally paid to acquire that asset, all the way through to what you receive when you sell the asset wh-when, when you've sold it in the future.

So it's taxing the economic gain from when you bought it to when you've disposed of it.

Do you think people are sufficiently aware of this, Daniel?

I asked him what it was about this gap that made him want to spend a lot of time researching and reporting on it.

Shortly after he was elected pope in 2013, uh, there were timelines of his life produced by the Catholic Church, and there was this gap, as you said, from 1990 to 1992 in which he was essentially doing nothing, uh, a very menial job at a parish in the city of Cordoba, far from his home city.

And I thought, "Well, that's interesting.

He goes from being a really powerful Jesuit, uh, to doing nothing, and then he's a powerful archbishop.

What- what is going on here? Why was he sent to this place? What did he do here?" And so I went with kind of an open mind.

Um, the m- the thing that I discovered that kept me going is the fact that he won't talk about it, and that's when I thought, "Oh, wow.

Th- there must be something really here that is still emotionally resonant for him."

I'm wondering how you as a person were affected by this assignment and what, if any, lessons you drew out of it about, about how sometimes your life can take a, take a wrong turn in terms of how you think it should go.