The Good News 2020

A visit these days to Leo High School for 1967 graduate Jim Carollo is more pilgrimage than a mere visit.

The reflective Carollo can vividly recall his altar-boy days walking from St. Leo’s Parish at 78th and Emerald to Leo’s chapel at 79th and Sangamon.

Today, the visionary Carollo is inspired to connect Leo’s storied past with the present and tomorrow, especially as Leo prepares for its 100th anniversary in 2026.

Carollo recently presented Leo Principal Shaka Rawls and Leo President Dan McGrath with one of those preparations: the inaugural Leo High School Brick Program fundraiser.

As expressed in the campaign, “Each alumni brick symbolizes a deep commitment to providing quality Catholic education for young men and embodies the hearts of alums who will be forever recognized for their institutional support.”

Carollo personifies today’s Leo alumni. For instance, last Veterans Day, the 1967 graduate arrived at Leo to engage students with a U.S. Medal of Honor, an encased family keepsake perfect for honoring United States soldiers.

As students gathered around in curiosity and awe, Carollo articulated the significance of the USA’s most prestigious military honor given to a soldier the students would never meet.

Carollo cherishes Leo as his personal “medal of honor.”

His induction in 2019 into the Leo Hall of Fame added to his enthusiasm. Familiar to the faculty and students, some of his greatest joys are just being around Leo students and men of any age as they gather for banquets, athletic events or golf outings.

Carollo has golfed in 15 Leo outings—including 11 straight—with brother Tom Carollo (Class of 1971) and cousins, Jim (’62) and Tony (’64), which included so many Leo hats that Jim Carollo gives them away as a way to promote Leo High School.

Carollo was the committee chairperson for the 50-year reunion of the Class of 1967, and he stays in close contact with his classmates, informing them and promoting activities of both the alumni and their alma mater.

He is a director of the Leo Alumni Association and an active participant in its monthly meetings. He has also played a crucial role in maintaining the alumni association’s email list. He volunteers for various functions, including the annual alumni golf outing.

Retired as purchasing manager for Sears Tower, Carollo follows the Leo mission of “facta non verba” or “deeds, not words” to help where he can.

“The pandemic has caused the cancellation of so many events for people, but it doesn’t mean that it has to stop us in our tracks,” said Carollo. “The Leo brick campaign speaks to the future of education for young men and allows us old men to be proud participants.”

For more information, contact Jim Carollo at (312) 498-6841 or