Grief and gratitude rarely feel like they’re packaged on the same train.

This winter-turning-spring, I’ve been swimming in both emotions regularly.

Grief that the curtains are closing on a deep-rooted passion I’ve had for nine years as the head basketball coach at Audubon Elementary.

Gratitude for every team I’ve coached and every kid I’ve had the privilege of influencing.

Grief of my father, whose death prompted me to coach as a balm for missing my best friend.

Gratitude for this 2025-26 team that reminded me of my own 8th grade team when my dad was my head coach.

When I first started coaching the Hawks in 2017, thanks to a cold call to an assistant principal I now call a close friend, I wanted to give back in my Roscoe Village community and help kids through a sport that forever bonded me with my dad.

Little did I know I’d be the one getting back so much in return from this volunteer gig that’s spanned for nearly a decade.

From my first-ever 2017-18 squad, when I was a spry 27 years old, I got a sense of acceptance. A group of seasoned 8th graders embraced me as their coach on the way to a city playoff Final Four finish, and from there, I was able to attach “Audubon basketball coach” to my identity through various phases of life.

From my 2019-20 squad that reached the city championship game a few short days before COVID flipped life upside down, I got a sense of pride from seeing them blossom from 5-foot-nothing 6th graders to puberty-infused 8th graders. Likewise, their coach grew alongside them.

From my 2022-23 city championship squad, forever known to themselves (and me) as the “banner boys,” I got a dose of history that derived from hard work (the start of dreaded 7am practices), as we hung up the school’s first major sports banner by winning it all and finishing 18-2 on the season.

  

From my 2023-24 team, I got to see the program’s growth, with 38 kids joining for one grade level as opposed to the 5-7 kids that would be on a team when I first started.

From my 2024-25 team that upset the No. 1 seed in our playoff bracket and handed an 18-0 team its first loss of the season, I got a chance to experience evolution – seeing a group of 5th graders who threw temper tantrums when they didn’t get a call gradually evolve into mature teens holding their coach back while he threw a tantrum at a horrific referee.

From my 2025-26 team this final season, in this “last dance,” I’ve learned how to practice what I preach to this group in channeling adversity (and heartbreak) into resiliency. A team that made up for lack of size and athleticism with heart and tenacity. I wouldn’t want my swan song to be with any other group.

During practices in this final season at 3500 North Hoyne, after climbing a seemingly endless three flights of stairs, I realized how much of a sanctuary the gym has become over the years through countless lessons I’ve taught the boys – all to the backdrop of drills that I learned from my former coach, George Limperis. It was in those practice hours where I felt my dad’s presence most. Where I talk to the boys about how much I believe in them yet also challenge them to reach the best of their abilities. It’s what my old man did for me – and sharing that gift/planting that seed, and seeing it bloom later in life, is what youth sports is all about.

This past December, I had a chance to host an Alumni game with nine generations of Hawks players. We had close to 50 former players who were all ready to battle each other for Audubon supremacy. I felt unbelievably moved that they showed up to honor me in my final season send-off. Having the opportunity to take in how much they’ve matured as young adults in college and high school made my heart feel so full. I was struck with a regular sense of deja vu when I’d see a 20-something kid make the same move he used to make when he was 13. Some of the players have stayed tight as a group over the years, despite going to different high schools and colleges. That close-knit camaraderie in 8th grade is as good as it gets, and became the perfect level for me to mold kids.

I realized through that Alumni game just how much my dad’s been with me the whole time. I told everyone that December day that every season I coached their particular team, it was bittersweet because I wished my dad could’ve seen them play and that I could’ve talked Xs and Os with him or raved about a Stephen, Parker, Elliott or Gordy performance. But at the same time, I see my dad in all of them now – as young adults who heeded the same lessons he passed down to me that they trusted me with at age 13. I see Dad in how they’ve applied what I taught them way back, whether that’s taking accountability for their actions, picking others up when they’re down, or channeling adversity to not get dejected when life doesn’t go their way.

The connection to the boys has been reciprocal, too. Over the various seasons of life –whether I was single and it was just me and my dog post-game or married and ready to start a family like I am now – you learn a lot about yourself through the kids who you reach. I learned how to be a better coach with every whistle and a better man with every interaction. Even when that interaction was, “we need to fire this damn coach.” (I see you, EJ). On top of what I’ve learned, my identity as coach at Audubon always gave me a sense of community through the players and parents that made me feel embraced and purposeful in the neighborhood.

  

As it often goes with grief, there’s a hell of a lot I’ll miss. Like yelling at referees (while calling them “sir”) and getting technical fouls (especially when my wife, Treslyn, had the camera out). I’ll miss the postgame locker room talks – after wins, of course…but especially after losses when it’s hard to process through difficult emotions that come with the black and whiteness of sports. I’ll miss giving out “hustle award” sweatbands to the kid who works the hardest and does the little things that don’t show up on the stat sheet. I’ll miss the bench players scoring their first – and sometimes only – basket of their playing career and for their teammates to go crazy on the bench as if we just won the Super Bowl, even carrying the kid off the court.

I’ll deeply miss the individual bonds with players, as I’ll cherish my 1-on-1 battles with the boys (even when I miraculously lose and owe the entire team Bulls tickets). And I’ll miss the camaraderie with the boys as a whole, what it means to create chemistry as a team – on and off the court through defensive slides, 11-man drill, Bulls games, pizza parties and the like.

As it goes with gratitude, there’s a ton I’m forever thankful for. To start off, I’m super grateful for my assistant coaches, especially this year. My first three years coaching, I didn’t have anyone on the sidelines with me. But for the past five years, Coach Febus has been there the entire time – banners, adversity and all. He’s a head coach-in-waiting ready to do big things, and I’m honored to be a part of his journey. Three years ago, Coach O’Donnell jumped in – and did so when he didn’t even have a son on the team. To have coached three of Bill’s sons showcases just how damn long I’ve been at the program. His comic relief, Tex Winter-style stats, and “blunt talk” with the boys to complement what we’re doing, was instrumental in us creating not just a great team, but a great program. And Coach Ruf jumped in this final season with regular Xs and Os talk and brilliant basketball intuition to only make me a far better coach.

  

I’m also going to miss the parents who have trusted me with leading their kids and have been a huge support over the years. At the Alumni game, getting one last chance to savor parents seeing their kids play in the bleachers was special. And the closer I get to fatherhood myself, the more I feel like I’ve learned from amazing parents who love their kids through the sport in such a meaningful way.

It’s unbelievably difficult to say goodbye to an endeavor like coaching when it’s so ingrained in your identity, but I can feel God pulling me to the next chapter. One lesson that resonated with me from this final season, when things didn’t go our way and our ending felt unfair, is how much basketball mirrors real life. And with that, no matter how many battles won or lost with each team I coached, I got to play a pivotal part in them being prepped for the war in the game of life. In that light, I may be retired, but I’ll always be their “coach.” And now, I get to take everything the boys changed me with along with me when I one day become a different type of coach – as a father.

I started coaching because I missed my dad. Uniquely, I feel empowered and ready to be a dad on my own now thanks to the last nine years as “Coach Gleeson.”

  

In the week since my final season concluded, I’ve been flooded with emotions and core hoops memories. But since the games (wins and losses) are the ones that stick the most, I’ve opted to include my top 10 games of my coaching career from 2017-2026 (with brief details why).

Top 10 games I’ve coached at Audubon

1. Audubon vs. Bateman, city championship win, 2022-23 season. Our academic-centric school had never won a city title at the time and this game had the environment of a rival high school game with an electric crowd. I’ll never forget time winding down on the clock and hoisting that trophy with all the players rallied in. It captured what we had worked so hard for starting back the previous season when I planted a “banner” in their minds as 7th graders.

2. Audubon vs. Blaine, city playoff quarterfinals upset win, 2024-25 season. I learned through this game that if you have two elite defenders, one of which competes for national championships in cross country, then the triangle-and-2 defense is the recipe to stun a previously unbeaten 18-0 team. That moment where I came into the locker room and yelled to the boys, “now we’re the best (expletive) team” will live in Audubon athletics lore.

3. Audubon vs. Disney, regular season upset win, 2018-19 season. We had some help from the refs with a mostly 7th-grade team playing elite 8th graders. But this was a home game that will always be top of the totem pole for me because Disney had been a powerhouse before this, having gone undefeated in the past couple of seasons and clearly overlooked us. My guards Parker and Quinn went off in this one, and when you storm the court afterwards, you know something special happened. It was a big momentum boost for this group going into a city runner-up finish the following year.

4. Audubon vs. Bell, city playoff quarterfinals win over rival, 2017-18 season. This first group I coached was as title worthy as any team I ever coached, and this was the game that showed their mettle against our archrival. When adversity hit, they rallied together and Cian’s clutch three-pointer was the momentum-shifter that advanced us to the next round. We almost knocked off a state-ranked Disney team the next game in the semis before injuries and BS fouls killed us.

5. Audubon vs. Bell, city playoff semifinals win, 2022-23 season. Beating Bell is always meaningful considering it’s the Duke-North Carolina of Roscoe Village. And that season, behind an Elliott O’Donnell-led banner squad, we beat Bell four times. The best win was the toughest one in the city semis to advance to the title game. Henry’s three-pointer on the right wing helped us seal the dub.

6. Audubon vs. St. Andrew, regular season double overtime win, 2025-26 season. In a home game against our Catholic school neighbor, we went point-for-point and possession-for-possession before we outlasted them in the final extra frame thanks to some silky jumpers by Knox. Having my uncle and wife sitting courtside made this one extra special, and winning in such an up-and-down thriller was a major highlight of my final season.

7. Audubon vs. Hamilton, regular season “khaki pants” win, 2019-20 season. JP will always be an Audubon icon for this one – forgetting gym shorts and dropping 30 points in his khakis to lift us to a quality home win. I’ve heard of lucky shorts but this was another level, with the pulled-up khakis giving him a superhuman jump shot.

8. Audubon vs. LaSalle, regular season come-from-behind win, 2021-22 season. This one was wild for a variety of reasons, including the opposing team’s fans getting into bizarre, stop-the-game verbal altercations with our fans. Their two best players fouled out in the third quarter, and we overcame a double-digit deficit to win a hard-nosed game and clinch the playoffs as a 7th grade-dominated squad, pre-banner season.

9. Audubon vs. Franklin, regular-season home win, 2024-25 season. Going into this game, I had waves of anxiety because I knew that we needed to win otherwise we would’ve missed the playoffs because our division was crazy tough that year. Gordy, Harry and Owen came ready and were on attack mode all game long to secure a playoff spot that eventually led to the biggest upset in our school history.

10. Audubon Gray vs. Waters, regular season road win, 2024-25 season. Our “C” Team hadn’t won a game all season in conference play and won this one by two in a game that went down to the wire. Seeing the boys come together to end their careers on a dub was special, and validated our decision to have three teams (with 30 plus players, no cuts) so that we could get everyone playing time.

Honorable Mention—Audubon Gray vs. Audubon Black, regular season Jamboree win, 2024-25 season. A banked-in buzzer-beater for our C Team to knock off our B Team. Shout out lil Tony.

Honorable Mention—Audubon vs. Harriett Tubman, regular season nail-biter win, 2022-23 season. With our best player Elliott OD out, Elie went full Hakeem Olajuwan and dropped 30 points to edge out a tough team in a season where we went 10-0 in conference.

Honorable Mention—Audubon vs. Bell, exhibition buzzer-beater, 2022-23 season. Beating Bell is always epic, but winning a come-from-behind game at the buzzer – even in exhibition – was as good as it gets.

Honorable Mention—Audubon vs. Bell, CPS League 19-point win, 2023-24 season. As mentioned, beating Bell was always satisfying and a 19-point beatdown was one of the highlights of this ’23-24 squad.