On February 18 – a Chicago Public Schools non-attendance day – 140 middle school students from 22 schools across Chicago gathered at the iconic Wintrust Arena for a day centered on two critical leadership pillars: communication and taking initiative.
As part of Urban Initiatives’ Take the Lead (TTL) program, these student Captains stepped off the sidelines and onto a premier stage to build the social capital and peer networks necessary to navigate high school and beyond. Most importantly, this impactful experience was provided entirely free of charge for all participating students, schools, and families.
Playing Like the Pros
The day was packed with energy as students participated in several rotations alongside peers from different schools and grade levels. The experience was designed to give them a “behind-the-scenes” look at professional athletics while building leadership skills:
- Locker Room Tours: Students explored the inner workings of the arena, gaining a new perspective on professional sports environments.
- Obstacle Courses: Captains navigated through the stands, testing their agility and endurance.
- Teambuilding Games: Rotations focused on collaborative play to strengthen communication between students who had never met.
- On-Court Play: Captains had the chance to play on the professional basketball court, a moment that sparked immense confidence.
The impact of being in such a prestigious space was clear; one student, inspired by the day’s activities, shared that he now knows he will “be famous one day.” Another student exclaimed “We’re on the Angel Reese court!” when jumping onto the basketball court for the first time that day.
The Power of Initiative: “Help” as a Superpower
The true success of the retreat was captured in the students’ own words.
In reflections gathered immediately following the activities at the event, one-quarter of all students specifically used the word “help.” This wasn’t a call for assistance, but a declaration of action.
It demonstrated that for this next generation of leaders, taking initiative means identifying where they can support their teammates and communities. By focusing on communication, these Captains are learning that the strongest leaders are those who reach out to lift others up.

A Home Court Advantage: Thank You, Wintrust Arena!
We want to extend a massive thank you to the team at Wintrust Arena for opening their doors to our students. For our 140 Captains, having access to such a vast, professional, and inspirational space made all the difference.
Wintrust Arena wasn’t just a venue; it was a relatable bridge to their dreams. Standing on the same court as their favorite pros and touring the locker rooms allowed our students to see themselves in these spaces, proving that their leadership has a place on the city’s biggest stages.
This environment turned a day of learning into an unforgettable experience where our students could truly feel like the leaders they are.
Why These Retreats Matter
Urban Initiatives’ work is anchored in a healing-centered approach. Research shows that youth who make meaningful connections with peers and adults are better positioned to excel in school and life.
At the Wintrust Arena retreat, our Captains focused on:
- Building Peer Networks: Connecting with student leaders from over 20 different CPS schools to develop transferable leadership skills like communication and taking initiative.
- Developing Social Capital: Gaining exposure to new places and ideas to help them navigate future challenges.
- Strengthening SEL Skills: Participating in group activities that promote teamwork, empathy, and initiative.
When we provide kids with caring coaches and structured leadership opportunities, we aren’t just playing a game – we are building a safer, more equitable city.




