Our First Flag Football Season: A HUGE SUCCESS!

As nightfall approaches, and often earlier, motorists tend to drive down 79th Street with their car windows up and their doors locked. They clench the steering wheel in a death grip and stare straight ahead, intimidated by the boarded-up storefronts and Auburn Gresham’s overblown reputation as a dangerous place. 

We see it all the time.

So you had to wonder what those motorists were thinking as they came upon a stretch of 79th Street between Morgan and Sangamon on Friday evening, Oct. 21. 

Dangerous? Hardly.

Kids were dashing about on a brightly lit field with smiles on their faces that matched the illumination. Cheerleaders, music, balloons, spectators numbering in the hundreds … all there for the championship game of the first Leo High School-sponsored Flag Football League, which brought energy, vitality and visibility to a community Leo has long been honored to serve.

When we applied for a grant to refurbish a field that was sorely in need of repair, we stipulated that the finished product would be a community resource and not just a Leo High School facility. The Chicago Bears and the NFL Grassroots Foundation took us at our word and approved the grant, and the project was completed in late summer. As a first step toward honoring our “community” pledge, we formed a flag football league for neighborhood elementary schools.

We started small, with sixth-through-eighth-grade co-ed teams from St. Sabina, the Academy of St. Benedict the African, Paul Cuffe STEM Academy and Barbara Sizemore Leadership Academy playing six weeks of Saturday-morning doubleheaders. At the conclusion of the double-round-robin schedule, ASBA was on top with a 5-1 record, followed by St. Sabina at 4-2.

Thus they qualified for the championship game, which was played “under the lights” to give it a little more pizazz. To say a good time was had by all is a gross understatement. 

St. Sabina was a little bigger and a little faster, with a strong-armed QB whom we hope to see throwing passes for Leo in the near future. Two late touchdowns gave our neighbors from South Racine a 33-21 victory over our friends from Englewood. From their joyous reaction, you’d have thought the Sabina kids won the lottery or the Super Bowl or both. 

Great night for the kids, great night for the community, great night for Leo, which is nothing if not a great neighbor to all who call Auburn Gresham home. And a salute to Leo Admissions Director Kevin McNair, who embraced the flag-football project from Day 1 and saw it through to fruition … only to realize he might have to work twice as hard next season.

We have already received inquiries from four additional schools hoping to join the league next year. We’ll be ready for them. 

Coach Holmes: One of a Kind

Coach Holmes.

The crowd for the Rich game was probably Leo’s largest of the year for a home game as dozens of Coach Holmes’ former players and other alums turned out to congratulate him and say thanks for 30-plus years of distinguished service to Leo.

A poster recounting his career highlights, a football autographed by this year’s team and gift cards to some of his favorite restaurants were among the gifts Coach Holmes received. He was honored at a reception at Leo following the game.

Over three-plus decades as an athlete,coach, classroom teacher and school administrator, no one has done more to embody the spirit of Leo High School than Mike Holmes ’76.

Coach was the Leo Alumni Association Man of the Year in 2018 and the Leo Lions Legacy Award recipient in 2020.

His most enduring legacy may be the dozens of Leo athletes who earned college scholarships while playing for him. Inspired by his example, many of them followed Coach Holmes into the coaching profession.

Among his other accomplishments: 

• Coach is one of the most decorated athletes in Leo history: All-American in football, All-State in baseball

• He was a double Lawless Award winner as Catholic League Player of the Year and Coach of the Year

• He has coached four additional Lawless Award winners, including son Aamir Holmes in 2016

• Under Coach Holmes the Lions have made multiple IHSA and Chicago Prep Bowl playoff appearances, including a state semifinal berth in 2013 

• Dozens of Leo student-athletes earned college scholarships while playing for Coach, and five went on to play pro football  

Coach Holmes has had a truly great and undeniably impactful run as the heart and soul of Leo High School.

An Honor for Principal Rawls

The Rev. Robert E. McLaughlin Faith Foundation challenges its supporters to invest in hope. 

It’s named after Rev. Robert E. McLaughlin, who devoted his career as a priest to improving the lives of young people. Since Fr. McLaughlin’s death in 2005, the Foundation started in his honor has offered financial support to organizations whose primary purpose is the betterment of young lives. Leo High School has been the recipient of McLaughlin Foundation grants for the last four years.

This year, the Foundation is also recognizing Leo Principal Shaka Rawls, whose commitment to bettering the lives of his students embodies the “spirit of hope” philosophy that informs the McLaughlin Foundation’s operations. 

Mr. Rawls will be honored at the Foundation’s annual golf outing and dinner at Park Ridge Country Club on Monday, Oct. 3, along with Helen Bruns Ryan, a generous, longtime supporter of Josephinum Academy. 

“It is not the things we get but the hearts we touch that determines our success in life.” The Foundation used that quote from Fr. McLaughlin in citing Mr. Rawls’ accomplishments at Leo, including a 60-percent enrollment increase and 100-percent graduation rate.

And this, from St. Ignatius Loyola: “Love ought to show itself more by deeds than by words.” Leo High School’s motto is Facta non Verba: deeds, not words.

“I very humbly accept this honor on behalf of Leo High School,” Mr. Rawls said. “It may be presented to an individual, but it recognizes the team effort that’s involved with everything we do at Leo.” 

Coach Holmes Farewell

Coach Mike Holmes’ hopes of going out with a playoff bang in his final season as the Leo Lions’ football coach suffered a blow with a four-game losing streak that followed an impressive season-opening win over Bulls Academy Prep.

Holmes, a 1976 Leo graduate and one of the most decorated athletes in school history, announced beforehand that the current season would be his last. Through two tours as head football coach, along with his contributions as a classroom teacher, school administrator, admissions director and vice president for advancement, no one has done more to embody the Spirit of Leo than Coach Holmes, and we thank him for 30-plus years of tireless effort and commitment.

He was the fifth recipient of the Leo Lions Legacy Award, in 2018, and the Leo Alumni Association named him its Man of the Year in 2017.

Coach Holmes will be honored at the school following the Senior Day regular-season finale against Rich Township on Saturday, October 22 at St. Rita’s Cronin Field.  

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

Leo’s Annual Black History Pageant

Leo’s annual Black History Pageant, held in the school auditorium on Friday, Feb. 18, seemed even more high-energy than usual because of the involvement of so many Leo students. 

Mr. Kevin Steward, who teaches biology, supervises the National Honor Society and serves as student-activities coordinator, organized the two-hour program that featured “motivational speakers, cultural custodians and teachers of the people … who empower us to follow our dreams,” in the words of BeInvinceable Productions, which provided the entertainment. 

The World-Renowned Leo Choir took center stage as the opening act, but another dozen Leo students had roles, including sophomore Keith Smith (rap) and senior Jarrett Blake (spoken word), who performed original compositions pointing out that the Black man’s struggle in America is ongoing.

Readings by seniors William Anderson, P.J. Brown, Cameron Cleveland and Jakolbi Wilson; juniors Isaiah Knox, Christopher Robinson and Thomas Sims and sophomores Christian Brockett and Zion Cornell-Strickland paid tribute to the work of such celebrated Black writers as Maya Angelou, Gwendolyn Brooks, Lorraine Hansberry, Langston Hughes, Richard Wright and Ralph Ellison, while other passages acknowledged the contributions of Black inventors Charles R. Drew (the blood bank), Lewis Latimer (the incandescent-filtered light bulb) and Garrett Morgan (the red/yellow/green stoplight).

In the midst of a soul-stirring drum performance, Deshaun and Elizabeth Newman pointed out the differences in drums from the different regions of Africa, but no matter their origin, drums played a vital role in various aspects of African culture. They also noted that American slave owners denied their enslaved people access to drums lest they communicate with the enslaved people on neighboring plantations and create unrest over their living and working conditions.   

By popular demand, Vincent Gray and Brian Kizer were back with a high-decibel spoken-word performance that brought Leo students to their feet when it was performed in this venue several months ago.

Gray is a product of the Auburn Gresham community who said he would have attended Leo if his parents had been able to afford the tuition. Thus his knowledge comes mostly from the streets, and he used common-sense street vernacular to emphasize the importance of good decision-making.

“I don’t hear no because I live in yes … Are you doing what’s necessary or what’s comfortable? … How many of you have an I-phone? How many of you have I will? … My library card is more valuable than my driver’s license because my library card takes me places my driver’s license can’t … Eighty percent of success is showing up. Eight-five percent is showing up on time … You don’t have a problem, you have a choice. A problem is an opportunity to rise to the occasion.”

Kizer said he dealt with rejection issues as a youngster—he was born out of wedlock, and his father refused to acknowledge or accept him. He seemed  headed for the street life and a “career” as a drug dealer until a cousin intervened and reminded him of the wisdom of their grandmother: “You can do more than you’re doing. You can be more than you are. You can become the man you’re supposed to be.”

Kizer closed by emphasizing the importance of belief in one’s self. ”I am water to a well. Put me anywhere on God’s green earth and I will succeed.”

Finally, what would a Leo celebration be without some recognition for Principal Shaka Rawls? This time it came from the Cook County branch of the Illinois Principals Association, which recognized Mr. Rawls as a “bridge builder,” citing Leo’s various efforts to better the lives of its Auburn Gresham neighbors.

“My name is on this plaque, but the award is for Leo High School,” Mr. Rawls said. “All of us are involved in the work that’s being recognized here today. And we intend to keep it going.”

The World Renowned Choir Performed at Halftime at Soldier Field



Leo Boys Choir Kicked Off Bears Halftime Entertainment on January 2

The school that played football in front of 120,000 Chicago fans in 1937 took center stage at historic Soldier Field for live halftime show

By Bill Figel, Community Contributor, Patch.com

The Leo Boys Choir regaled the Soldier Field halftime crowd Sunday with their rendition of the Blues classic “Sweet Home Chicago” during the Bears and Giants game. “Ain’t No Stoppin’ Us Now” was also featured in the Leo Boys Choir’s halftime performance Sunday during the Bears Game. 

Leo High School’s return engagement at Soldier Field speaks volumes as to how much the South Side school has evolved from its days as a gridiron powerhouse to a coveted choir group singing at halftime of the Bears contest against the New York Giants at noon.

Leo represented the Catholic League in the 1937 Prep Bowl against Austin that drew a crowd estimated at 120,000, still regarded as the largest crowd for an American football contest.

A commonplace fundraising engine, the Chicago Mayor’s Charity Game, also known as the Mayor Kelly Bowl, pitted the champion of the Chicago Catholic League against the champion of the Chicago Public League. Reportedly, everyone from politicians to firefighters were buying and selling tickets for the game.

The Chicago Tribune reported the game “raised $100,000 for the City’s Christmas Fund used to clothe needy kids.”

Hitting all the right notes will trump hitting the open receiver Sunday. Soldier Field’s halftime show was the setting for Leo Boys Choir, regarded for its versatility and harmony on and off the field.

“Presenting the arts expression of Leo to a broader audience is landmark for us,” said Leo Principal Shaka Rawls. “While sports has been our calling card for decades, academics, the arts, debate, chess and especially choir has opened doors for Leo and each Leo student heading into the world.”

Pandemic pressures have caused Leo choir to audible, adjusting its schedule to generally accommodate audience schedules. The challenged has not dampened the choir’s enthusiasm and the extensive practice has elevated their collective voice.

“When the young men perform as they did at the Four Seasons earlier in December, their spirits are lifted along with their audience,” said Choir Director Ms. LaDonna Hill. “Our young men have a resiliency that permeates beyond the choir. These life lessons dealing with adversity and still giving their best will serve them well in life.”

Leo was a repeat Prep Bowl champion in 1941-42, beating Tilden both years. In a 1956 Prep Bowl appearance the Lions enjoyed a satisfying 12-0 victory over neighborhood rival Calumet.

Leo’s most recent to visit to Soldier Field garnered a victory over Lane Tech of the Chicago Public on Friday, August 25, 2018 as part of the annual Kickoff Classic tripleheader marking the beginning of the Chicago-area high school football season. At the time it was and the Lions’ first Soldier Field appearance in 43 years, dating back to 1974 season, when a Bob Foster-coached Leo team dropped a 24-8 decision to Brother Rice in a Catholic League playoff semifinal.

The Catholic League joined the Illinois High School Association in 1974 and became eligible for IHSA-sanctioned state playoffs that robbed both the Catholic League playoffs and the Prep Bowl of much of their luster as CCL teams set their eyes on state championships. Mount Carmel, Loyola Academy and Providence Catholic have been particularly successful in that pursuit.

“What a great opportunity for our young men to perform, singing on a field where so much history has been made,” said Leo Coach Michael Holmes, a junior starter for the Lions at tight end and defensive end on the 1974 team. “We’ve been working hard to raise Leo’s profile, and being invited to sing at Soldier Field is an indication that those efforts are paying off.”

Chicago Magazine: Shaka Rawls, CHICAGOAN OF THE YEAR 2021

Shaka Rawls: Creating safer spaces for young men of color

As many local schools shuttered for summer break this year, Shaka Rawls, the principal of Leo Catholic High School, transformed the all-boys school into a tuition-free camp.

Rawls created what he calls an “enclave” in the Auburn Gresham neighborhood to protect the roughly 60 students who enrolled in the summer camp from the crime, poverty, gangs, and gun violence that hang low and heavy when school’s out.

“We felt like it was better to have our boys safely within our grasp,” says Rawls. “We are safer together here in this building.”

Because grades weren’t given at camp, there was no fear of making mistakes, Rawls says. There was just math, English, and ACT prep, followed by afternoons of building robots and writing code, creating mosaics, or playing with spatial articulation.

Rawls’s educational approach flows from a place of love and deep understanding. After all, the 46-year-old was once a “whippersnapper” who graduated in 1993 from the very high school he now leads. Rawls says he sees himself in his boys and them in him.

That connection works.

Since Rawls became principal in 2016, he’s instituted a science, technology, engineering, and math initiative. The high school continues to have a 100 percent graduation and college acceptance rate.

In a world where the lives of Black and brown boys on the South and West Sides of Chicago are disproportionately bombarded with things no human should have to wrestle with — fear, violence, racism, police brutality — Rawls spends his days (and many nights) nurturing, encouraging, and celebrating his 210 students, 94 percent of whom are Black, 6 percent of whom are Latino.

He and his staff work to fine-tune the students’ strengths and talents, instill a sense of purpose, and ensure they never doubt their worth. Rawls is quick to reach out if he sees one of his students wander or stumble. He estimates more than half of his students have his mobile phone number, which they use frequently.

Although he has spent the bulk of his career in administration and policy, Rawls sees himself as more of a social activist than an educator. His work, he explains, is merely a natural extension of who he is. The sense of community caregiving and advocacy Rawls promotes is an ethos, not an indoctrination, and is organic for incoming freshmen, like hopping on a train that already exists.

New students are expected to bring unique ideas to engage the community. They learn they are part of a brotherhood, in service to one another. “Our whole vocabulary is about how we are interdependent, not just inside the high school, but our community at large,” Rawls says.

This year, Rawls was inspired by a school billboard with the tagline “In a time of social distancing, Leo is bringing people together.” So he did it — virtually.

To demolish the “us and them” narrative between law enforcement and young Black and brown men, Rawls set up a series of web conferences with his students and a stream of police and military officers, FBI agents, prosecutors, and judges. The floor — or rather the chat box — was open.

The principal’s hope was that the experience would help both his students and the law enforcement officials see each other as fellow human beings.

“We wanted to dismantle this socially constructed disconnect and bring them together in the same space and realize that we all want the same thing: We have families we love; we have faith in God and community,” Rawls says. “We all want to go home at night.”