Now, in an exclusive interview, and as Krashesky prepares to retire this week, he talked with Cardinal Blase Cupich on key issues of today and what the future holds.
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In those four decades, Krashesky has covered three Chicago Cardinal-Archbishops, as well as three popes in Rome.
Cardinal Cupich was the first choice of Pope Francis when picking the top leadership for American Catholics.
One thing the cardinal made clear was that he is not going anywhere and wants to stay in Chicago.
"I love Chicago and I want to stay here," the 74-year-old cardinal said.
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The cardinal already spends considerable time in Rome, serving in positions that include choosing future bishops and the structure of worship.
We've seen him, at times, actually working at the Pope's right hand.
"I've made it clear to people over there this is a good fit for me," Cardinal Cupich said without saying he's already turned down a permanent job there. "Chicago is my home and I'm going to retire here."
It's been eight years since the former Bishop of Spokane, Washington, was tapped by Pope Francis to come to Chicago.
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Krashesky said one of his personal favorite interviews occurred back in 2014, just before the cardinal came to Chicago. He said he joined Cardinal Cupich as he drove across eastern Washington State to attend a football game between Catholic high school rival.
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The priest, who is originally from Omaha, still enjoys interaction with young people.
"I like doing that kind of thing. I think that, when I got to basketball games at some of our schools, we sit on one side and then on the other," Cardinal Cupich said.
There's a bit of diplomacy in that, but his focus on relationships has helped him in building interfaith relationships, including leading Muslim-Catholic talks at the national level.
"I do have a good relationship with the Muslim community, and also the Jewish community," Cardinal Cupich said. "I think, especially with the rise of anti-Semitism."
July of 2019 is one key moment of solidarity that stand out, when Holocaust survivor Fritzie Fritzshall invited the cardinal and Krashesky to accompany her as she returned to Auschwitz, the former Nazi concentration camp where Fritzie was imprisoned as a teenager. It was also where a number of her family members died or were killed.
RELATED: Holocaust survivor Fritzie Fritzshall returns to Auschwitz with Cardinal Blase Cupich
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Holocaust survivor Fritzie Fritzshall returns to Auschwitz with Cardinal Blase Cupich
"She said to me, 'You know, I know you believe in God. I struggle with that,'" Cardinal Cupich recalled. "She said, 'Because God was sitting on the shelf on the sideline when everything was happening.'"
Cardinal Cupich has certainly faced challenges, including when a state attorney general reviewed the handling of sexual abuse cases involving priests, even as some critically demand even more transparency.
But the cardinal believes the current process used by the Archdiocese now is a good one.
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"But I tell people, I want it done right. So it is not a matter of how long it takes, but how well it's done," Cardinal Cupich said.
With the U.S. Supreme Court decision on abortion, and states now splitting between abortion rights and abortion bans, Cardinal Cupich said he acknowledges the difficult decisions women are forced to face.
"What the church is saying - that we're saying- is 'Don't forget about the baby,'" Cardinal Cupich said. "Let's make sure that we have a wrap-around program of support after birth, as the child grows up. I believe that's a starting point maybe, in which we can have some agreement."
The cardinal believes one of the greatest challenges we face is cutting through the division and polarization in our society. He said breakthroughs occur when people actually sit down and talk to each other, and that's not only among politicians and groups with different viewpoints, but among religious leaders and people of different faiths.