Still Chasing What’s Possible

Twenty years ago, on an October morning in Chicago, Deena Kastor stood at the start of the Chicago Marathon with one clear goal: to win. She had already accomplished what eludes most American women distance runners: earning recognition as one of the sport’s most respected figures. Yet, remarkably, she had never actually won a marathon.

“I was only focused on winning the race,” she says. “It seemed really strange to me that I was in this sport and finding success in it, and I had an Olympic medal and the American record, but I had never actually won a race.”

Just weeks before the marathon, Kastor rolled her ankle on a pinecone and suffered a stress reaction in her foot. Most runners would have taken time off. She adapted. “I immediately jumped into the pool in the underwater treadmill and just kept my mind focused on this race. I only focused on what I gained in that process, and it was a truly immense experience. It gave me tremendous clarity, much like having blinders on race day.

“Instead of seeing injury as loss, she turned it into an opportunity. “You know, I think, as a runner, the night or two before the race, it’s always like, ‘Oh, I wish I had more time or did another long run.’ And there are very few instances that any of us toe the line, really feeling confident in our preparation and our ability to execute the race plan. However, this was one of those days where I just felt like I was the best prepared I could be.”

Her build-up included a half-marathon in Philadelphia, where she broke the American record. “I knew I had maintained my fitness,” she says. “That solidified that I was still on the right track.”

The Race That Defined Her

On race morning, Kastor was laser-focused — perhaps too much so. “I was really fired up… one of my training partners turned to me, and he’s like, ‘That was way too fast.’ And I said, ‘The mile’s short.’” Constantina Tomescu-Dita of Romania, the defending champion,

matched her stride for stride. “She was on my shoulder, and I’m like, ‘What is she doing with me? I’m running hard.’ So, I would put in a surge to try to drop her… at some point, I had almost a minute lead on her, but that narrowed down to only three seconds by the finish.”

Kastor laughs now, remembering how fiercely she fought that day. “I was running with a scowl the whole time,” she says, smiling. “It was so intense that I probably still need a shot of Botox to get rid of it—twenty years later!”

The race came down to sheer will. She doesn’t remember crossing the line or the cameras capturing her victory. “I don’t remember the interview. I was completely just absolutely defeated. I remember the screeching of the gate and my mom yelling, ‘Get her a chair.’ That’s the first thing I remember.”

Later that day, standing at the window of her hotel room, Kastor looked at the runners still finishing. “My family and I were standing there, and I joined my sister at the window, watching all the runners. It made me feel so proud to be a part of it.”

Coming Back Stronger

A decade later, Kastor returned to Chicago. This time, she was chasing the American master’s record. But once again, the path was anything but smooth. “I had bad allergies, I was dealing with wildfires, and then two weeks before the race, I got the flu. I was a wreck.” She told her husband, Andrew, that she was thinking of dropping out.

Andrew reminded her of everything she had already accomplished in training. “He started listing all the things I had done. My longest long runs in the past decade, my longest tempo runs of my entire career, and I’m still running five-minute pace repeats on Tuesday mornings. He said, ‘Despite missing some workouts, you’re entirely capable of breaking this record.’”

That reminder shifted her perspective. “I realized both stories were true — the one full of excuses, and the one that supported what I wanted to accomplish. So, I chose the story that helped me.” The race itself was far from perfect. I missed grabbing my water bottle at the aid tables, I stumbled mid-course, and I felt the familiar sting of fatigue.

Yet, with each challenge, she adapted. “With every one of those moments, I just re-engaged. I thought, I’ve come too far. What do I do next? I got to the finish line, and I had broken the record by almost a minute. I was seventh place, but it was a win in the sense that I was able to reach my goal under difficult circumstances.”

Her 2005 victory burned with fire; her 2015 race was steadied by faith. Both taught her the same truth: endurance isn’t only about strength. It’s about grace under pressure and the courage to keep moving when everything tells you to stop.

Mind, Body, and the Art of Adaptation

Few athletes articulate the connection between body and mind as clearly as Deena Kastor. “I think you need 100% of both,” she says. “So many of us focus on the physical training program, but we don’t necessarily focus on how we can adjust our thoughts. If we can control some of those 75,000 thoughts a day and make them work in our favor, we’d be in a much better place.”

For Kastor, running has always been about the harmony between preparation and perspective. “Trust your training, whether it went perfectly or was flawed. Run the mile that you’re in and don’t overthink it. Wherever you need to put your head to get the best out of yourself, that’s your greatest advocacy on race day.”

She breaks down the marathon and life into manageable moments. “I like to divide the marathon not into 42 kilometers or 26.2 miles—that’s too much—but into water bottles. There are eight of them, and I can digest eight. Eight segments of this race I need to count.” That approach, focused, flexible, and self-aware, has shaped not only her running but her life philosophy. “I don’t think anything that happens to us is good or bad,” she reflects. “There are just circumstances, and we have to find a way to grow in them.”

Passing the Torch

Now in her fifties, Kastor’s role in the sport has evolved from champion to mentor, from competitor to community-builder. “I love putting medals around runners’ necks. Their accomplishment is written all over their faces. It fills my cup.”

This year, she was back in Chicago doing just that, placing medals around the necks of finishers two decades after her own triumph. It’s a full-circle moment that captures what running, and life, have come to mean to her: gratitude, connection, and joy shared freely.

Her career came full circle when she had the chance to celebrate others, just as her idols once celebrated her. “After I broke Joan Benoit Samuelson’s record in London, she called me and said, ‘I knew it would be you.’” “When Kira D’Amato broke the American women’s marathon record in Houston, I called to congratulate her. And when Emily Sisson broke it here in Chicago in 2022, Joan, Kira, and I were all there at the finish line. That was really special. Runners need to support each other, and for women to support other women in this sport.”

The Journey Continues

In 2019, Kastor completed her Abbott World Marathon Majors Six Star journey. “I was really surprised how meaningful it was. When I think of who I was when I ran New York for the first time, and who I grew to become, getting that six-star was a big deal to me.” She treasures each medal not just for the achievement but for the story behind it. “When I see a medal, I don’t think of the time I ran, I think of a memory tied to it.” That includes one that still makes her laugh: a dinner with Constantina Tomescu-Dita, her onetime rival in Chicago.

“When I look back at my London Marathon medal, I think of the dinner that Constantina and I shared the night before the race. I said, ‘Aren’t you going to eat pasta?’ and she said she was having fish. Then I ordered tiramisu, and she looked at me like, ‘You’re eating tiramisu before the race?’” She laughs. “We were friends who’d soon be competitors once the gun fired that morning.

That’s what the sport gives you: connection.” This year, she ran the inaugural Sydney Marathon in 2025 as part of its debut as a Major. “I was super underprepared, but I was in awe of my body’s ability to run that course. Everything about Sydney was just lovely. If Cape Town becomes the next Major, you bet the Kastor family will be there.“

Even after decades of achievements, her joy comes from the same place it always has: the act of showing up. “I’m less proud of any individual thing I’ve accomplished and prouder of that constant journey. I still love getting out the door before sunrise to run with friends. I’ll never retire from something that fills me.”

Legacy: Kindness and Insatiability

When asked what she hopes to leave behind, Kastor doesn’t talk about medals or records. She talks about people. “I hope it’s sparking kindness and inclusion across all walks of life. I think our sport is getting better at representing everyone, and I’d like people who haven’t felt safe before to feel safer participating in this sport. I hope people feel kindness and a sense of purpose that motivates them to keep going. Nothing’s career-capping, nothing’s life-altering. We keep moving forward, and I hope people prioritize their mental fitness.”

Twenty years after her Chicago triumph, Deena Kastor runs with the same heart, but with a steadier flame. What once burned to prove herself now lights the way for others, fueling purpose, gratitude, and the quiet confidence to keep chasing what’s possible. Her joy now comes not from finishing first, but from continuing to evolve. Proof that results don’t measure the most significant victories, but by how we grow through every mile. In running and in life, she reminds us that endurance isn’t just about strength, it’s about showing up with heart, hope, and grace, mile after mile. 

Dr. Maria Bendeck is a board-certified internal medicine physician, freelance writer, world traveler, avid marathon runner, and community builder. She believes in embracing life to the fullest by exploring new places, helping others, and empowering people through writing.