Ray Siegel Receives the Andy McKenna Leo Legacy Award

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.

Graduation Day 2023

By Dan McGrath

The weather was cool, damp and threatening, but it couldn’t dim the spirit in and around the church as Leo High School held its 94th commencement celebration for the Class of 2023 at St. Margaret of Scotland on Sunday, May 14 – Mother’s Day.

Forty-two seniors received diplomas before a packed house of family, friends and relatives. The sheer joy and exultation that greeted the announcement of each graduate’s name was a reminder of what a truly special occasion this was.

Mrs. Tiffany Harston, Leo’s guidance counselor, did a splendid job as MC for the program. President Dan McGrath and Principal Shaka Rawls commended the class for dealing with COVID’s many challenges as effectively as they did in making it through to graduation. The world-renowned Leo Choir performed. Each senior presented his mother with a Mother’s Day poem he had composed as a Senior English writing project for Mr. Redmond’s class.

But, in an unusual twist,  the highlight of the day was the speeches.

Matthew Hernandez displayed the poise and confidence he said he was grateful for acquiring during his Leo journey, one that saw him become an honor student, class Salutatorian, National Honor Society member and all-conference baseball player.

Esai Jacinto said he never would have had the nerve to deliver a speech to a packed house when he entered Leo as a nervous little freshman, not knowing anyone and not sure he belonged. But he not only was accepted, he was challenged to become all he could be at Leo: Valedictorian, honor roll, National Honor Society, varsity wrestler, four-year baseball starter. 

Esai grew emotional as he thanked his family, his friends, his teachers, his classmates and his coaches—especially Coach Mike Anderson—for helping him find the path to success at Leo. Several people were seen dabbing at their eyes as he went down the list.

In an amazing display of personal connection, Principal Rawls used his speech to recall an interaction or an anecdote about each senior in the graduating class. Nothing pro forma; every message was personalized to let the young man know he’d been recognized and appreciated as a Leo student.

“And now you’re going out into the world as a Leo Man,” Mr. Rawls said. “Make us proud.”

Jacinto and Tim Durr took home two gold medals apiece as Senior Award recipients. The complete list:

• William J. Koloseike Gold Medal for Athletics: Kevin Jackson
• Bishop John R. Gorman Gold Medal for Religion: Jonathan Agee
• Michael L. Thompson Gold Medal for Music: Timothy Durr
• Donald F. Flynn Gold Medal for History: Matthew Hernandez
• Dr. James J. Ahern Gold Medal for Science: Timothy Durr
• Thomas and Mary Owens Gold Medal for Mathematics: Thomas Sims
• Stafford L. Hood Gold Medal for English: Esai Jacinto
• Br. James Glos Gold Medal for Foreign Language: Dorion Woods
• Frank W. Considine Gold Medal for Social Justice: Christopher Robinson
• Andrew J. McKenna Gold Medal for Leadership: Esai Jacinto 

Congratulations to all the members of the Class of 2023 and their families.

And many thanks to the faculty, staff and parent volunteers who put together a spectacular day for Leo.

We’ll do it again next year … and for many years to come.  

Jamal Thompson, Leo Basketball Coach, Steps Down

Jamal Thompson ’00 has stepped down after four seasons as Leo High School’s varsity basketball coach. A search is under way for his successor.

“This is disappointing, to say the least,” Leo President Dan McGrath said. “We like Jamal, as a coach but more important as a person. He did a good job at Leo and brought the best out in our players. We thank him for his contributions and we wish him well in his future endeavors.”

Thompson won the Lawless Award as Chicago Catholic League Coach of the Year last season after guiding the Lions to their first CCL championship since 2010 with a 13-1 conference record. They added regional and sectional titles before losing to DePaul Prep in a Class 2-A Supersectional, finishing 25-5 overall.

Thompson’s overall record with the Lions was 76-27. He won two regional and two sectional titles and was inducted into the Leo Hall of Fame in April 2022.

Transportation to Leo Information

Transportation will begin August 22, 2022 and is offered to each student who attends Leo High School on a first come, first serve basis. Transportation is only offered for before school pick-up. Students are responsible for their own transportation after school. Students will be picked up at a designated location and time. This service typically starts the following week after Labor Day.

The cost is $50.00 per month. Total amount is $450 for the year and will be added to your tuition.

You will be contacted by your designated bus driver once routes and times are set. If you have any questions, please contact the Main Office at 773-224-9600.

Please complete the form below via link or QR Code. Thank you!


We Are Proud of Our 2022 Graduates

Sunday, May 8 was a festive, joyous day to remember for Leo High School’s graduating class of 2022, as well as their mothers as Leo upheld a longstanding tradition of graduating on Mother’s Day before a full house at St. Margaret of Scotland Church.

It was an especially festive and joyous day for two standout members of the class, whose many contributions over four years were acknowledged and honored.

In his Valedictorian address, Cameron Cleveland cited the obstacles he and his classmates overcame to reach graduation in the midst of a COVID pandemic that affected every aspect of their high school careers. Classroom success, basketball triumphs, community-boosting service projects … all seemed even more meaningful, having been achieved against a COVID backdrop that disrupted so many lives in so many ways.

Ranked No. 1 in his class for each of his four years at Leo, Cleveland earned the Valedictorian designation for finishing with the highest GPA within the Class of 2022. Befitting the two-year captain of Leo’s Catholic League championship basketball team, he also received the William J. Koloseike Gold Medal for Athletics, as well as the Thomas and Mary Owens Gold Medal for Excellence in Mathematics and the Andrew J. McKenna Gold Medal for Leadership Initiatives.

Cleveland is headed for Morehouse College in Atlanta on an academic scholarship.

Oliver Brown Jr. —known as PJ around Leo—was the Class of 2022 Salutatorian by a razor-thin margin. He echoed Cleveland in noting that COVID-induced challenges brought his classmates closer and gave them a greater appreciation of high school experiences they might otherwise have taken for granted or even missed altogether.

Brown, who as “PJ the Deejay” was the MC for numerous Leo events over his four years, also received the Stafford L. Hood Gold Medal for Excellence in English and the Frank W. Considine Gold Medal for Social Justice. He is headed for Southern University in Baton Rouge, La,., on scholarship for baseball and academics.

Mother’s Day set a delightful tone for the ceremony. In one highlight, each graduate presented his mom with a framed copy of a Mother’s Day poem he had written to complete his Senior English project for Mr. Titus Redmond’s class.The world-renowned Leo Choir’s four-song set featured stirring solos by senior Robert Smith (“It’s So Hard to Say Goodbye”) and sophomore Theauntae Jones (“See You Again”), as well as a lively rendition of “Ain’t No Stoppin’ Us Now” that brought the crowd to its feet to join in.

And in a speech that encapsulated the last four years, Principal Shaka Rawls reminded the graduates that the resolve they displayed in committing to their education as COVID upended their lives would serve them well as they move forward in life … as true Leo Men.

The complete list of honorees from the Class of 2022:

The William J. Koloseike Gold Medal for Athletics: Cameron Cleveland

The Bishop John R. Gorman Gold Medal for Religion: James E’Akels

The Michael L. Thompson Gold Medal for Music: Jacori Elam

The Donald F. Flynn Gold Medal for History: David Gross

The Dr. James J. Ahern Gold Medal for Science: Wellington Porter

The Thomas & Mary Owens Gold Medal for Mathematics: Cameron Cleveland

The Dr. Stafford L. Hood Gold Medal for English: Oliver Brown Jr.

The Brother James Glos Gold Medal for Foeign Language: Jakolbi Wilson

The Frank W. Considine Gold Medal for Social Justice: Oliver Brown Jr.

The Andrew J. McKenna Gold Medal for Leadership: Cameron Cleveland

You’re Invited to Our STEM Family Night on October 7

Leo High School’s STEM Department invites you to our STEM Family Night on Thursday, October 7, from 5:30 to 7 p.m. in the Cafeteria.

Get ready for hands-on fun for the whole family including SCIENCE, TECHNOLOGY, ENGINEERING and MATH activities!

FREE Hot dogs, chips and popcorn.

• Get extra credit
• Make slime
• Fly a glider
• Build a boat

Principal Rawls named “Man of Excellence” by the Chicago Defender

Leo Principal Shaka Rawls has been recognized as a “Man of Excellence” by the Chicago Defender, one of the nation’s oldest and most influential Black news organizations.

The Defender’s Men of Excellence awards celebrate African-American men who “inspire others through excellence, vision, leadership, exceptional achievement and a commitment to empowerment in multiple ways.”  

Other Men of Excellence honorees for 2021 include ABC-7 TV personality Hosea Sanders, 18th Ward Alderman Derrick Curtis, Metropolitan Peace Initiatives Executive Director Vaughn Bryant and State Representative Kam Buckner, a South Side Democrat from Illinois’ 26th District.

Leo’s enrollment has increased by more than 60 percent since Principal Rawls arrived in 2016. Additionally, his leadership has enabled Leo to become a truly positive force in the Auburn-Gresham community through various service projects, such as a free meals program that helped feed hundreds of families  when the COVID pandemic was at its worst in the spring and summer of 2020. 

“Everything we do at Leo is a team effort, so I accept this award on behalf of the Leo team,” Mr. Rawls said. “Coming from an organization with the history and prestige of the Chicago Defender, it is truly an honor.” 

 The Defender cites Principal Rawls and his fellow honorees as “champions of empowerment and diversity, the backbone of religious and educational organizations and driving forces in politics and community service.”

They will be honored at a dinner on Friday, Aug. 27 at Haven Entertainment Center, 930 E. 43rd Street, beginning at 6 p.m. 

Baseball Facility at St. Rita Named for Jay Standring ’66

Leo great Jay Standring ’66 will remember 2021 as a year in which he was celebrated for a life well lived.

Last May, St. Rita High School recognized Standring’s 30-plus years of service as an ever-popular  coach, teacher and mentor by naming the freshman baseball facility in his honor—Jaybird Field. 

In September, and for largely the same reasons, Notre Dame’s Knute Rockne Foundation will honor 1970 ND grad Standring with a Knute Rockne Spirit of Sports Leadership Award.

“Knute Rockne did not believe sports should be an end in themselves,” the citation states. “Rather, he saw them as a means to achieving success in life, with the lessons learned on the playing field translating to determination, teamwork and character in real life.” 

Jay Standring embraced that philosophy during his playing career, and he has embodied it throughout his coaching/teaching  career. He began it shortly after graduating from Notre Dame, where he earned two letters, intercepted three passes and played on two Cotton Bowl teams under Coach Ara Parseghian, whom he viewed as a role model.

“Every coach I played for had an impact on my life, and I went into coaching hoping to give kids opportunities similar to the ones I had,” Standring said.

He currently coaches freshman football and baseball at St. Rita. He has always preferred working at the lower levels; in many cases he’s the first coach a young athlete encounters, and he goes out of his way to make sure the experience is a positive one. The Rockne Award surely proves that coaching has been a positive experience for Jay Standring.

“It was never about recognition,” he said, “but an award like this from Notre Dame, which will always hold a special place in my heart … I’ve had a great life.”

Leo Golf Outing the Largest in the Last Few Years

Clear skies, great weather, a sellout crowd, nice prizes, some good and some not-so-good golf … it all added up to tremendously successful golf outing for the Leo Alumni Association, which brought the event back to Gleneagles Golf Club on August 6 after a one-year, COVID-induced hiatus.  

A full complement of 288 golfers meant both Gleneagles courses were at max capacity for the 9 a.m. shotgun start. A handful of unregistered players who showed up were also allowed into the field, making it the largest for a Leo outing in the last few years.

Co-chairmen Dennis Barista ’74 and Scott Fulwiler ’74 are to be commended for skillfully and successfully managing the event down to its last detail.

The O’Malley foursome—Tom O’Malley Jr. and his son Ryan; Mike O’Malley and his son Mike Jr.—was the day’s big winner, shooting 10 under par in the scramble format. That was one stroke better than the 9 under carded by Jack Fitzgerald ’69, Phil Rogers, Jim Kennedy and Jim Earner, a 1973 Brother Rice grad who serves as Leo’s Business Manager …  and whose dad Gene is a noteworthy Leo graduate, along with six Earner brothers.

A raffle, a silent auction and a sitdown dinner featuring Gleneagles’ famed fried chicken wrapped up the day. Good golf or bad, a good time was had by all.

Leo Men Welcome Students to the First Day of School

With Leo’s enrollment reaching its highest total in more than a dozen years, it was fitting that a larger-than-ever alumni contingent was on hand to greet the students as they returned to school for Opening Day on Thursday, Aug. 19, the first full day of classes.

“Opening Day”—inviting Leo’s alumni back for the first day of school—is a concept conceived by Principal Shaka Rawls four years ago to celebrate how Leo Men connect across the generations. The turnout grows larger each year. More than 50 alums formed up in the courtyard this year to shake the students’ hands, welcome them to the Leo brotherhood and reinforce the notion that by enrolling at Leo, they’re becoming part of something special.

Delightfully bright, sunny weather was further affirmation.  

Jim Furlong ’65, a highly decorated Vietnam war veteran and author of a book recounting his war experiences and their aftermath, was one of the older alums. Ri’chard Coleman ’21, headed for his freshman year at the University of Dubuque next week, was the youngest. 

The guest list also included Greg Richmond, newly named Superintendent of Catholic Schools for the Archdiocese of Chicago.

With the 8 a.m. first bell of the day bringing an end to courtyard festivities, all hands adjourned to the auditorium for a brief assembly. Superintendent  Richmond accepted an invitation to speak. A longtime Chicago resident, he is familiar with the Leo story and praised the alums as the “backbone of Leo,” thanking them for the support that has enabled the school to persist through challenging times.

Principal Rawls followed with a rousing speech about expectations. It was directed at the students, but several alums found themselves tucking in their shirts, buttoning some buttons and making other adjustments to be sure they complied with Mr. Rawls’ idea of presentable.