The Daredevil of Chicago: Why Angelo Perez Refuses to Stay Down

By: Juan Ortiz, Host of Chicago Grit

If you follow Angelo Perez on social media, you see a superhero. At 57 years old, he is tearing through life with a ferocity that puts men half his age to shame. In recent years, he has completed the Chicago Marathon, thrown himself out of a plane skydiving, and explored the ocean depths scuba diving in Mexico.

My own kids have given him a nickname: "The Daredevil."

It fits perfectly. He lives by a simple, thrill-seeking creed: "I always like to do things that people say don't do." When the world tells him something is too hard, his response is always the same: "Why not?"

But the real dare isn't the skydiving or the marathon. It’s that he does all of it from a wheelchair.

In the latest episode of the Chicago Grit podcast, I sat down with Angelo to understand the engine behind this relentless motion. What I found was that his grit wasn't born in a gym. It was forged in the fires of 1990s Chicago, and honed through a lifetime of climbing mountains, falling off, and choosing to climb again.

The First Rise and Fall

Before he was an elite athlete, Angelo was a product of his environment. Raised in Chicago’s Pilsen and Gage Park neighborhoods, he didn't just participate in the street life—he led it. Rising to become a division leader in the Ambrose gang, he adopted an invincible persona necessary for survival.

That invincibility shattered on August 28, 1991. At 23 years old, a bullet from a drive-by shooting tore through Angelo’s spinal cord. The street leader was suddenly told he would never walk again.

Most people would have stayed down. Angelo chose to rise. He removed his gang tattoos, found wheelchair sports, and won "Rookie of the Year" in 1996. He was climbing.

The Paradox: The Scholar and the Addict

But the climb wasn't a straight line. The decades that followed were a chaotic war fought on two fronts. This is the definition of the "Unfair Advantage"—the ability to endure what would break most people.

Angelo lived a paradox that is hard to comprehend. On one track, he was rising academically. He earned his GED, became a lecturer, and eventually earned a Master's degree in Social Work from UIC.

But while he was achieving in the classroom, he was falling in the streets. He was battling a severe crack cocaine addiction that saw him homeless and desperate. He recounts stories that sound like fiction—like flipping a car on a Chicago median while high, hanging upside down by his seatbelt as semis roared past. He was a man capable of earning a Master's degree, yet trapped in a wreck of his own making.

The False Summit and the Nursing Home

In 2012, Angelo reached a summit: he graduated with his Master's degree. But life has a way of humbling you just when you think you've won.

Immediately following his graduation, a severe health crisis stripped him of his independence. He lost his apartment. He lost his momentum. For the next six years (2012-2018), he lived in a nursing home.

This was the ultimate test. He had climbed the mountain of education, only to fall all the way back down to institutional confinement.

The Renaissance: Covid Grit

But the story of Angelo Perez is that the climb never stops. In 2018, he fought his way out of the nursing home. He started over. Again.

The perfect metaphor for this "Second Life" happened during the COVID-19 lockdowns. With gyms closed, Angelo called me up to borrow a handcycle I wasn't using. Refusing to let his momentum die, he rode endless laps through the cemetery behind his house.

While the world was locked down, Angelo Perez was riding through a graveyard just to feel alive.

The Legacy of Jackie

Through the gang life, the shooting, the degrees, the addiction, and the nursing home, one person was the constant: his late mother, Jackie DeLeon. She was the "silent person in the room" who never stopped believing in him.

"I think that's where I got my grit from," Angelo told me. "Watching her grind and make things happen out of nothing."

Today, Angelo honors her legacy by building a future for others. Alongside Chicago Adaptive Sports, he is advocating for a world-class Paralympic facility in Chicago—a centralized hub where the next generation can find their own strength, without having to survive the same fire he did.

The Grit is in the Climb

Angelo Perez teaches us that resilience isn't about reaching the peak and staying there. It’s about the jagged, messy reality of being human.

He climbed. He fell. He climbed higher. He fell lower. And every single time, he looked up at the summit and started pushing his wheels forward.