MILWAUKEE — Cathy Connelly-Warren spent parts of a long Sunday night in Wisconsin awake and unable to sleep, staring at the wall in her hotel room “thinking of speeches,” she said. The “good speech,” as she put it, promised to be easy. If her daughter qualified for the U.S. Olympic Team in speedskating, the moment would speak for itself.

But what if she didn’t? What if there was more heartbreak after so much of it? What to say then?

Connelly-Warren arrived at the Pettit National Ice Center on Monday prepared for both outcomes on the final day of Olympic trials in long track. She and her family gathered along the edge of the ice and near the finish line, hearts pounding. The starting gun fired. Sarah Warren, who had been dreaming of the Olympics for almost 20 years, burst into a furious sprint.

Five hundred meters and a little more than 38 seconds later, she crossed the finish line, pumped her fists and released a celebratory scream. She cried. The first person she hugged was her mom and they held each other in an emotional embrace. After torn ACLs in both of her knees, 10 surgeries and countless rejections of those who told her it might be time to quit, Sarah Warren had done it.

She’d qualified for the Olympics. She’d made Team USA. She’s off to Milan next month.

Few American Olympians — or those anywhere else — will have endured as long and difficult a journey to Italy. In the past year alone, the 29-year-old Warren, who grew up in Willowbrook and attended Hinsdale South High School, underwent four surgeries: three on her knees and one on an ankle. She never quite felt back to full strength, she said, not even on Monday — not that she could feel anything other than elation after one of the longest days of her life.

“You envision the moment your whole career, and it’s pretty surreal,” said Warren, who now calls Chicago home. “You come across the line, you look up, and it’s hard to describe that feeling, but the emotion was just the army it took to get me here. I have to admit, my imagery before the race was hugging my family after.

“And so the crying, yes — I dreamed of this since I was a little girl.”

Warren, who began skating when she was about 10 years old, grew up around competition and sports. Her dad, Morrison, played rugby and football at Occidental College. Her brother, John, played football and rugby at the University of Chicago. Her great-uncle is Kevin Warren, known to most as the Chicago Bears president but to Sarah as “Uncle Kevin.”

“He’s also like my grandfather,” she said. “It’s just so much wisdom from him. He’s fought tooth and nail to be where he is, and he takes every opportunity. And Uncle Kevin’s a huge role model for me.”

Sarah Warren skates in the women's 500-meter event on her way to a second place finish and qualifying for the Milan Olympics, Jan. 5, 2026, during the U.S. Olympic Team Trials Long Track at the Pettit National Ice Center in Milwaukee. (Brian Cassella/Chicago Tribune)Sarah Warren skates in the women’s 500-meter event on her way to a second-place finish and qualifying for the Milan Olympics, Jan. 5, 2026, during the U.S. Olympic Team Trials Long Track at the Pettit National Ice Center in Milwaukee. (Brian Cassella/Chicago Tribune)

Sarah tried to ignore her phone most of Monday. When she looked at it after the race, though, the first congratulatory text message she received was from Uncle Kevin. He had been in meetings at Bears headquarters inside Halas Hall on Monday when one of his assistants reminded him that it was time. He retreated to his office, tuned into the broadcast and watched Sarah take the ice.

As she made the first turn, her time and pace exactly where they needed to be, Kevin Warren said he “could not hold back the emotions.”

“I just started to sob,” he said during a phone interview Tuesday. “I said, ‘She’s going to get it done.’ I was so emotional. I just even get emotional, now.”

His thoughts drifted to when his nephew Morrison — Sarah’s father — met Cathy, and “just all the dreams that we used to talk about.” They’d all wanted their children “to be good people and hard workers,” Kevin Warren said.

Bears President Kevin Warren, from left, his great-niece Sarah Warren and nephew Morrison Warren pose after Sarah's University of Illinois women's soccer team played against the University of Minnesota in 2016. (Warren family photo)Bears President Kevin Warren, from left, his great-niece Sarah Warren and nephew Morrison Warren after Sarah’s University of Illinois soccer team played the University of Minnesota in 2016. (Warren family photo)

And then soon enough Sarah came along with the grandest of dreams. Olympic dreams.

When Sarah Warren competes in the 2026 Winter Games, it will be a few days after the Super Bowl. Even if the Bears make it that far, the NFL season will not overlap with her competition, and so Kevin Warren on Tuesday was planning to be in Milan to cheer her on.

“We are taking the whole family,” he said. “Just would not miss this. And so we’ll be there. All of us.”

The past few days in Milwaukee brought back memories of practices and competitions at the Pettit National Ice Center, with Connelly-Warren driving Sarah from Chicago four times a week. As Connelly-Warren walked around the arena in recent days, she could remember tying Sarah’s skates when she was little. They saw familiar faces everywhere.

A standout soccer player, too, Warren pursued that sport and played at the University of Illinois, where she suffered the torn ACLs.

Quitting was never an option. Not soccer and certainly not skating.

She’d come to consider herself from a family of “always fighters,” she said.

“And that’s something that, being a Warren, you don’t really have a choice.”

Still, it wasn’t until last October, she said, when she felt healthy enough to start believing that the Olympics could be more than a dream. And then came the first day of the women’s 500-meter event at trials, on Sunday, when she put herself in position.

She and the others with a serious chance of qualifying began that race knowing they were likely competing for second place. And, indeed, Erin Jackson, among the sport’s stars and a favorite to repeat as the gold medalist in the event, came in first Sunday with relative ease. Warren, though, finished a breathless sprint in second place, and by the narrowest of margins.

When she left the rink Sunday, she was in position to qualify for the Olympics by .02 seconds. And then she had an entire night and most of Monday to think about holding on to her spot. If Warren didn’t match or exceed her time Monday, and if someone was faster than her Sunday time of 38.86 seconds, well — that’d be it. Dream over.

And after the ACL injuries and the 10 surgeries, would there be another shot?

“It’s always the question, right?” she asked. “I think through these surgeries, you know, you can’t take anything for granted.

“So I stepped on that line thinking this could be my last trials.”

It was “do or die,” she said, and her finish in 38.66 seconds was almost .02 seconds faster than her first time Sunday. She’d left no doubt, it turned out, and Warren became the third Chicago-area speedskater to qualify for Milan, along with Oak Park native Emery Lehman and Ethan Cepuran of Glen Ellyn. They both qualified individually (Lehman in the 1500 meters and Cepuran in mass start) and make up two-thirds of a team pursuit squad that’s aiming for gold next month.

Sarah Warren skates to celebrate with her mom, Cathy Connelly-Warren, after finishing second in the women's 500-meter event and qualifying for the Milan Olympics, Jan. 5, 2026, during the U.S. Olympic Team Trials Long Track at the Pettit National Ice Center in Milwaukee. (Brian Cassella/Chicago Tribune)Sarah Warren skates to celebrate with her mom, Cathy Connelly-Warren, after finishing second in the women’s 500-meter event and qualifying for the Milan Olympics, Jan. 5, 2026, during the U.S. Olympic Team Trials Long Track at the Pettit National Ice Center in Milwaukee. (Brian Cassella/Chicago Tribune)

When Warren crossed the finish line Monday, it looked a lot like it did during her visualization exercises. She’d spent a good part of Sunday night and Monday before her race envisioning what it would be like to secure her place in the Olympics. She saw the jubilant celebration. The hug with her mom. The embrace of family.

And when she wasn’t envisioning those things, she watched the movie “Moana.”

“I was like, I need my girl,” she said of the film’s title character.

While her mom spent hours before the race thinking of consoling words that she never had to use, Warren put her phone in do not disturb mode and tried to remain in the moment. There was no point in trying to pretend the opportunity in front of her was smaller than she knew it was.

“It was huge,” she said. “And at the end of the day it came down to 38.6 seconds of you’re going to be an Olympian, or not.”

And so she positioned herself at the starting line. The gun popped. Her mom and family braced themselves. And 38.66 seconds later, a dream that seemed improbable, if not impossible, amid all the torn ligaments and surgeries was no longer a dream at all.