Cardinal Cupich spent Dec. 7, the second Sunday of Advent, with a segment of the church not often seen — men incarcerated in Cook County Jail’s Division 9, a maximum-security division.

“There is a saying in the church that where the bishop is, the church is there,” Cardinal Cupich told the men. “And so today, the church in the Archdiocese of Chicago is here with you. You are in many ways the place where we celebrate as a church this Second Sunday of Advent.”

The archdiocese’s Kolbe House Jail Ministry organized the Mass observing the Jubilee of Prisoners as part of the Jubilee of Hope. It was part of the Catholic Prison Ministries Coalition’s effort to have bishops around the country celebrate Masses in jails or prisons before Pope Leo XIV’s Dec. 14 Mass for the Jubilee of Prisoners in St. Peter’s Basilica.

Pope Francis opened the Jubilee of Hope on Christmas Eve 2024 and it continues until Jan. 6, 2026.

A holy year or jubilee is a time of pilgrimage, prayer, repentance and acts of mercy, based on the Old Testament tradition of a jubilee year of rest, forgiveness and renewal. Holy years also are a time when Catholics make pilgrimages to designated churches and shrines, recite special prayers, go to confession and receive Communion to receive a plenary indulgence, which is a remission of the temporal punishment due for one’s sins.

The Holy See designated jubilee days throughout 2025 to recognize and celebrate different groups of people and various ministries in the church. Catholics from the Archdiocese of Chicago took part in several of these pilgrimages including jubilees for deacons, vowed religious and young people.

Pope Francis designated Dec. 14, 2025, as a special Jubilee for Prisoners, with a specific focus on the millions worldwide who are incarcerated, detained or awaiting execution.

According to the Bureau of Justice Statistics, 1,852,900 people were held in state or federal prisons or local jails, accounting for almost one-third of the total population under correctional supervision.

The U.S. has the highest proportion of its residents in prison in the world, according to the Institute for Criminal Policy Research. The Prison Policy Initiative, a MacArthur Foundation grantee, notes that the U.S. has the highest incarceration rate of any independent democracy globally.

Dressed in uniforms with “Cook County DOC” printed on them, about 20 men attended the bilingual Mass with Cardinal Cupich. Men from the congregation also proclaimed the first and second readings and the responsorial.

In his homily, Cardinal Cupich expanded on the Gospel reading about John the Baptist. John the Baptist, the last of the great prophets, shows us how to recognize Jesus in our lives, the cardinal said.

“Prophets are those that recognize something that others ignore,” he said in English and Spanish. “John sees that Jesus is the Messiah promised by Isaiah the prophet.”

John shows us three things about Jesus and the first is Jesus’ suffering heart, Cardinal Cupich said.

“He knows the sufferings of people. He also knows their difficulties,” the cardinal said. “He does not judge others by their appearances or by what other people say.”

Advent is a time for us to draw closer to Jesus who knows our histories, including our failures, he told the congregation.

“But he also knows the good that we have done, things that other people do not recognize,” he said. “Others may judge us by our mistakes, but Jesus doesn’t. He knows who we are.”

Jesus also sees that justice isn’t just about punishment, Cardinal Cupich told the incarcerated men.

“For Jesus, justice without mercy doesn’t exist,” he said. “He always wants to give us a second chance. All of us want a second opportunity in life and not to be judged by the worst things we have done.”

John sees that Jesus gives us opportunities to change because he wants to heal us, he said.  

“This is the Jesus we should get to know in these days leading up to Christmas — the one who wants to come into our life to give us another opportunity to tell us that he sees that we are more than our mistakes and that he comes to heal us,” Cardinal Cupich said.

John the Baptist also sees that Jesus wants to give us a peace that is more than the absence of violence or war, he continued.

“It is a peace that allows us to see that there is so much that unites us rather than divides us as a human family,” the cardinal said. “It is also a peace that we have with people who come from different lands, different places.”

As we approach Christmas, we want to come to know Jesus who knows us intimately and wants the best for us, he said.

“Let us pray that our eyes are opened in this holy season,” Cardinal Cupich said.

During the general intercessions, Cardinal Cupich invited the men to offer up their personal intentions and many shared them aloud. Several prayed for their families.

“I pray for my family and everyone in this chapel,” one man prayed.

“I pray for my wife who is battling cancer,” another man prayed.

“We pray for all the men and women who live here and for all the men and women who work here and support this place,” one man prayed.

During the sign of peace, after exchanging handshakes and embracing each other, many of the men approached the altar and exchanged a handshake of peace with a smiling Cardinal Cupich and the other ministers.

Cardinal Cupich personally gave Communion to the men.