"It saddened me, but this is a man who lived a full life at 95," said Cupich.
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That's when he learned that Pope Emeritus Benedict XVI had died at his home on Vatican grounds.
"As a theologian, he was an individual who was curious and wanted to know more about what others thought," said Cupich.
Cupich spoke with ABC7 from inside the ornate Holy Name Cathedral in Chicago's Gold Coast, where Christmas trees are still shimmering inside the sanctuary and a photo of Pope Benedict the XVI sits on display next to the altar.
"He was always very pleasant," reflected Cupich. "Sharp mind, very quick to pick up on things and also someone who respected the views of other people."
Benedict was born in Germany in 1927 as Joseph Ratzinger and served as the head of the Catholic Church for eight years starting in 2005, after Pope John Paul II. He resigned in 2013.
"Of course, he'll be remembered as the pope in 600 years who resigned," said Cupich. "This is a unique moment in history where you have a retired pope. There really is no game plan for that but Pope Francis carried it off quite well."
Benedict was seen as a guardian of traditional Catholic values condemning gay marriage, the ordination of women and allowing priests to marry.
He also addressed the Church's sexual abuse crisis during a visit to the United States in 2008 where he privately spoke with victims of priests.
Some said the scandals played a role in his retirement while Benedict claimed he left his post because of his declining health.
"No words of mine could describe the pain and harm inflicted by such abuse," Benedict said in 2008.
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Benedict spent retirement in seclusion, living in a converted monastery at the Vatican.
"I think he will be remembered as a man who was single-focused on serving others and serving God," said Cupich.
Benedict's life will be celebrated during a mass at Holy Name at 8 a.m. this Monday.
Archdiocese of Chicago auxiliary bishops will also preside at memorial Masses for Pope Benedict XVI in each of the archdiocese's six vicariates on Wednesday and Thursday. The public is welcome.
The times and locations are listed below:
Vicariate I:
Thursday, Jan. 5 at 7 p.m. at St. Theresa Parish, 455 N. Benton St., Palatine
Vicariate II:
Thursday, Jan. 5 at 7:30 p.m. at St. Joseph Church, 1747 Lake Ave., Wilmette
Vicariate III:
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Wednesday, Jan. 4 at 7 p.m. at St. Hyacinth's Basilica, 3636 W. Wolfram St., Chicago
Mass will be said in three languages: English, Spanish and Polish.
Vicariate IV:
Thursday, Jan. 5 at 6:30 p.m. at St. Cletus Church, 600 W. 55th St., La Grange
Mass will be in English and Spanish.
Vicariate V:
Thursday, Jan. 5 at St. Albert the Great Church, 8000 S. Linder Ave., Burbank.
Mass will be said in three languages: English, Spanish and Polish
Vicariate VI:
Thursday, Jan. 5 at 7 p.m. at St. Thomas the Apostle Church, 5472 S. Kimbark Ave., Chicago