Ray Siegel, who graduated from Leo with the Class of 1965, has been named the eighth recipient of the Andy McKenna Legacy Award. Ray will be honored at Leo’s eighth annual Scholarship Benefit on Wednesday, Nov. 29 at the Four Seasons Chicago Hotel.

The Legacy Award’s first recipient, in 2016, was Andy McKenna ’47, who died in February 2023. Mr. McKenna established himself as one of Leo’s most distinguished graduates during a lifetime of service to others. He was especially proud of his ties to Leo.

We chose to honor Andy at the first Scholarship Benefit, held in conjunction with Leo’s 90th anniversary, and a who’s-who of Chicago business and civic leaders turned out to help Leo say thank you. The inaugural event was so successful that it has become an annual affair, raising nearly $7 million for scholarship assistance to deserving young Leo Men.

“Ray joins seven other recipients of our highest honor, and he’s an ideal choice to receive the Legacy Award in a year when we’ll surely be remembering Andy McKenna,” Leo President Dan McGrath said. “Across the board, Ray has been one of our most loyal and generous supporters, in ways that extend beyond financial. Ray is a true role model and a true exemplar of Facta non Verba—Deeds not Words.”

A graduate of St. Margaret of Scotland elementary school, Ray transferred into Leo as a junior to extend his football career after St. Ignatius dropped the sport. He wanted to keep playing because he believed he’d need a scholarship to continue on to college. Over two years he became an All-Catholic League and All-City defensive lineman for the Lions.

An ankle injury sustained late in his senior year curtailed his recruiting, but Ray received a scholarship to St. Joseph’s College in Rensselaer, Indiana, where he enjoyed a standout career under former Leo coaching legend Jim Arenberg.  

After earning graduate degrees from Northern Illinois and Northwestern University’s Kellogg School of Management, Ray embarked on a successful business career. Today he heads RJS Associates LTD, a corporate financial consulting firm. 

Ray has spoken to Leo students about financial literacy, emphasizing careful spending and saving money as necessities. With COVID disrupting so many lives in 2020, he contributed seed money for Leo to establish an emergency fund that served more than 20,000 meals and provided medical supplies, groceries and household goods to Leo families and our Auburn Gresham neighbors who’d lost jobs or had their work hours cut by the pandemic. He also helps underwrite the Back to School Jam each year.

When Ray and his wife Lynn downsized from their Winnetka home to a Northbrook condo, they donated a mint-condition Steinway baby grand piano to the world-renowned Leo Choir. Ray provided funding for the Corporal John P. Fardy memorial plaque that will be unveiled at this year’s Veterans Observance on Nov. 3; Corporal Fardy, a U.S. Marine who graduated from Leo in 1940, was posthumously awarded the Congressional Medal of Honor for actions that cost him his life but saved his platoon at the battle for Okinawa during World War II.

In 2022, Ray received the Doc Driscoll Award for above-and-beyond service to Leo from the Leo Alumni Association.  

“There is no greater mission than to assist in the education of young men,” Ray said. “Being a small part of the Leo Mission is an important part of my life, but my contributions are nothing compared with what the staff at Leo does.

“I am stunned by this honor and I humbly accept.”  

Previous Leo Lions Legacy Award recipients:

2106—Andy McKenna ’47
2017–Bill Conlon ’63
2018–Tom Owens ’54
2019–Bob Sheehy ’71
2020–Michael Holmes ’76
2021–Maj. Gen. William Walker (USA-ret.) ’75
2022–Joseph A. Power Jr. ’70
2023–Raymond J. Siegel ’65