By Dan McGrath

The eighth annual Leo Scholarship Benefit was one of our school’s most festive … and successful.

A capacity crowd of 300 packed the Grand Ballroom of the Four Seasons Downtown on Wednesday, Nov. 29 to honor Ray Siegel ’65 and to beef up the Leo Scholarship Fund, on which there is more demand than ever as a result of this year’s substantial enrollment increase.

In terms of star power, the world-renowned Leo Choir, under the direction of Mrs. LaDonna Hill, performed three songs. Lourdes Duarte, from WGN-TV, did such a masterful job as MC that there was talk of offering her the permanent position. Father Tom Hurley, a good friend to the Siegel family as well as to Leo, offered the invocation.

Ray Siegel is the eighth Leo Scholarship Benefit honoree, but the first to receive the Andy McKenna Leo Legacy Award. The name change was made to honor Andy McKenna ’47, the first recipient, who died in February 2023 after a lifetime of service to others, including decades of strong support for Leo.

“Ray is ideal for this award because he truly emulates Andy in his selfless commitment to Leo and the Leo Mission,” School President Dan McGrath said. “It is our honor to honor him.”

Several McKenna grandchildren filled a table as Andy’s spirit permeated the room. Bobby Sullivan wore the Leo sweater Andy had been presented as the 2016 honoree. He joined Bill Conlon ’63 (2017) Bob Sheehy ’71 (2019) Mike Holmes ’76 (2020) and Joe Power ’70 (2022) in the sweater presentation to Ray Siegel, after the five former Lion football stars reminisced about their days at Leo and recounted what the school has meant to them over the years.

Mr. Siegel explained his commitment to Leo in a video, stating that he was inspired to do more by a speech he heard Principal Shaka Rawls give in his first year at Leo. Another video featured senior Theauntae Jones and the two-hour daily commute he endures from the West Side so he can attend Leo, “where I belong.”

Principal Rawls gave a typically high-spirited speech about the enrollment increase being symbolic of Leo’s upward trajectory.

“We’re the fastest growing school in the city,” he proclaimed, “and we’re only getting started.”

Mr. Rawls then brought seniors Zion Cornell and Roosevelt Nelson and juniors Lordan Black and Ian Dunn to the stage for a wide-ranging discussion of Leo today. Dunn got a laugh when he acknowledged Mr. Rawls as his favorite teacher/administrator, then added, “He told me to say that.”

With all proceeds earmarked for the Leo Scholarship Fund, the event was expected to clear $500,000 after expenses.

“Just a great night for Leo,” Mr. Rawls said.