Cool Pressure
The Caleb Williams Centerpiece
"Caleb The Bear Williams #18"
48" x 60"
oil on canvas
Tennessee gave me my first love in football. I was born there, and the Titans still have a corner of my heart. But Chicago taught me what it means to wait.
This city has waited decades for a quarterback who makes the whole lakefront hold its breath. Then Caleb Williams showed up, and Chicago exhaled.
The man on the canvas
On September 13, he did something no one in NFL history had ever done. Against Carolina he threw for 250 yards, ran for 50 more, and scored twice through the air and twice on his own two feet, all in one afternoon.
Then the injury. Three weeks of silence. Three Sundays of a city staring at the sideline, asking the same question.
On October 18 he came back and answered it. Thirty of 36 passes against Atlanta, the most accurate game a Bears quarterback has ever played, and a 31 to 23 win.
Two days later, I set down my brush. He’d come back, and the painting was done.
Where the rules go quiet
A traditional portrait is a conversation with my training: light, form, structure, the principles drilled into me year after year. I respect those rules. This painting isn’t one of those conversations.
I call it street pop art, because the style hasn’t told me its real name yet. Here, the rules step aside and the bag comes open. I scrape. I drip. I fling paint across the canvas. I reach for plastics and tools that have no business near a portrait and dare them to surprise me. Somewhere in that mess, the light bulb comes on.
What came out is 48 by 60 inches of grit and nerve. Texture built up, scraped back, built up again. “Cool Pressure” runs bold across the surface, loud as a stadium. Beneath it, “Ice in his veins,” quiet, like something whispered on the sideline in the fourth quarter. And standing alone, cold and certain, one word: ICE.
It’s a painting about a player who stays calm while everything around him burns. The painting asked the same of me.
Still learning
Every canvas like this reminds me that I haven’t arrived, and I hope I never do. I’m still growing and still experimenting. I still feel that rush I felt as a kid every time I make something new, and even more every time I learn something new.
Stand next to it
Right now the centerpiece is on the easel in my studio at the Zhou B Art Center, before it heads off to be framed. Come see it while the paint is still finding its voice. Stand beside it, take your picture, and make it part of your Bears story.
It’s piece one of a 21-piece collection. The 16 by 20 pieces are available for $550. Once signed at an athlete signing session, their value climbs to around $1,000.
The Dallis Flowers Portrait
Caleb's Painting is Loud. This one doesn't need to be.
"Dallis The Bear Flowers #37"
14" x 18"
oil on canvas panels
A Chicago Story
Dallis Flowers was born right here in Chicago in 1997. His road to the NFL didn’t run through a big-name program or draft-day cameras. It ran through Grand View and Pittsburg State, small schools where he earned NAIA All-American honors twice, and where very few scouts were watching.
In 2022, all 32 teams passed on him in the draft. He signed with the Colts anyway, made the roster as a rookie, and led the entire league in kick return average. Then, in 2023, his Achilles tore.
What came after is the part that rarely makes the highlight reel. He was waived, picked up by Tampa Bay, by San Francisco, and waived again. It meant practice squads, short contracts, and a lot of starting over.
In 2025 he came home and signed with the Bears. This season he’s on injured reserve, working his way back once more.
That’s the man I wanted to paint: not the moment of glory, but the man who keeps showing up.
Stripping it down
With Caleb, I opened the whole bag: scraping, dripping, throwing paint, building texture on texture. For Dallis, I put most of it away.
This 14" x 18" is black and white only. on a plain white background. There are no words or slogans. Every loose, brushy strokes, each one left exactly where it landed, with no color to hide behind and no going back to fix it. Every mark either works or it doesn’t, and you can see all of them.
That felt honest for a player whose career has been the same way, out in the open with nothing to hide behind. Black and white is where you find out what a painting is really made of. A comeback works the same way.
Two moods, one collection
Next to each other, the two pieces almost argue. Caleb is the roar of the stadium on Sunday. Dallis is the quiet hours that nobody films: the rehab, the film room, the phone call that might or might not come.
Chicago football is both of those things, and I wanted both on the wall.
Not for sale
This portrait isn’t for sale. It isn’t really finished either, at least not the story behind it. Soon I’ll sit down with Dallis himself to talk about what an athlete and an artist might build together. I don’t know yet where that conversation leads, and that’s the exciting part.
Come see it
Until then, the Dallis Flowers portrait is in my studio at the Zhou B Art Center right now, on its way to framing. Come stand in front of it, look closely at the brushwork, and see how much a painting can say with only black and white.