“Alcatraz was never intended to be a place of rehabilitation” Warden Edwin W. Swope, Alcatraz 1948-1955. 

On September 21, I lined up for what would become my best triathlon of the season, the Oktoberfest Sprint at Union Reservoir outside Longmont. My splits—12:59 for the half-mile swim, 36:10 for the 12.9-mile bike, and 23:03 for the 5K run—were my strongest combination all year. I finished 3rd in my age group and 57th overall out of 461 competitors. For a guy who’s been wrestling not just with the usual aches, pains, and the grind of training, but also the “shadows in my head”—work, family, and the ever-present demands of criminal justice reform—this race was more than a podium finish. It was a reminder of what endurance really means.

The Oktoberfest Race: A Personal Best

Oktoberfest was the culmination of a season punctuated by setbacks, minor injuries, and the persistent struggle to find time to train. The lead-up was less than ideal: the rec center pool had closed for three and a half weeks in August, so my first swim after the break was just four days before the race. I’d been running and biking, but avoiding the pool—a classic case of letting the shadows take over.

Race day was crisp and clear, the kind of morning that makes you believe anything is possible. I went into the swim with a simple goal: find a rhythm, stay calm, and keep pushing forward. My time—12:59 for a half-mile—was the payoff for years of managing open water anxiety and learning to “confront my fears” where I’m most vulnerable. The bike leg felt smooth and strong; my winter hours on the trainer in the “hurt locker” paid off as I cruised past younger athletes on bikes that cost more than my first “newer” car. On the run, I dug deep, chasing a 7:25 per mile pace and catching as many competitors as I could until the final stretch.

Crossing the finish line, I was drenched in sweat, legs aching, but fully alive. Third in my age group, 57th out of 461 overall—those numbers meant less to me than the sense of having mastered, at least for a day, the shadows that so often threaten to pull us under.

The Endurance Mindset: Lessons from the Course

Racing triathlons, like working for criminal justice reform, is about more than speed or strength. It’s about resilience, patience, and the willingness to keep grinding even when the odds are stacked against you. I’ve written before about the parallels between endurance sports and justice work: both require a kind of stubborn optimism, a belief that change is possible, even when progress is slow or invisible.

Most people don’t realize how much a triathlon can mirror the criminal justice system itself. The swim—often chaotic, sometimes terrifying—reminds me of the confusion and fear faced by those entering the justice system for the first time. The bike segment, with its long stretches of focus and bursts of intensity, feels like the grind of advocacy work: mostly steady, sometimes exhilarating, always demanding. The run is the final test, a reckoning with fatigue and doubt, where mental strength counts as much as physical.

Next Up: Escape from Alcatraz

With Oktoberfest in the rearview mirror, my sights are set on the Escape from Alcatraz Triathlon in San Francisco on June 7. This race is legendary: for 45 years, athletes from around the world have gathered to attempt a challenge once thought impossible—escaping the island prison’s icy grip and conquering the city’s brutal terrain.

This year, the 46th running will draw thousands from all 50 states and more than 50 countries. The course is a gauntlet: a 1.5-mile swim from the waters near Alcatraz Island (yes, the real deal), an 18-mile bike through the Presidio’s rolling hills, and a punishing 8-mile run that includes the infamous Sand Ladder—a climb so steep and sandy it’s broken the will of many. The finish line at Marina Green is as iconic as it gets.

Why is Escape from Alcatraz considered a bucket-list event? Because the swim alone is a psychological and physical crucible. The water is bone-chilling, the currents unpredictable, and the distance daunting. It’s the same stretch that dashed the hopes of countless real-life prisoners during Alcatraz’s years as a federal penitentiary. The prison was built in 1934 to house America’s most dangerous criminals—Al Capone, “Machine Gun” Kelly, and others. With its isolation, frigid waters, and swirling tides, escape was deemed impossible.

Yet in June, we’ll leap from the ferry, hearts pounding, into those same currents. We’ll swim not just against the tide, but against history itself, testing whether endurance, preparation, and a little bit of madness can overcome the impossible.

Alcatraz: The Prison, the Myth, the Metaphor

Alcatraz operated as a federal prison from 1934 to 1963. Its reputation for brutality and inescapability was legendary. The 1.25 miles of cold water separating it from San Francisco, with currents that could sweep a person out to sea, made it the ultimate symbol of confinement. There were 14 known escape attempts; only three men—Frank Morris and the Anglin brothers—were never found. Myth holds that they perished in the waters, but the dream of escape endures.

For me, the Alcatraz swim is more than just a race. It’s a metaphor for the barriers that so many face in the criminal justice system. The currents of public opinion, policy inertia, and entrenched power structures can feel as relentless as the tides. But history is full of people who refused to accept impossible odds. Like those who attempted to escape the prison, reformers and advocates fight every day to find a way forward, believing that change—however remote—is worth pursuing.

Racing and Reform: Two Paths to Redemption

My journey through endurance sports began in my mid-30s, when I realized that running, biking, and swimming were more than just ways to stay fit. They became a means to regain control over my body, to push back against the aging process, and to forge a sense of purpose that transcended the finish line.

The same can be said of my work in criminal justice. After 20 years as a public defender, prosecutor, and parole board counsel, I came to see that real reform is slow, grueling, and rarely linear. It demands the same qualities that endurance sports cultivate: patience, persistence, and the willingness to keep showing up, even when you’re not sure you’ll ever see the results.

We live in a country where more than two million people are incarcerated—a number that has grown by 700% since the 1970s, even as crime rates have remained relatively stable. The reasons are complex: punitive sentencing, a focus on retribution over rehabilitation, and a political climate that rewards tough-on-crime rhetoric. But just as escape from Alcatraz was once deemed impossible, so too does criminal justice reform often feel like an unattainable goal.

And yet, every so often, there’s a breakthrough—a new law, a successful reentry program, a person who finds redemption against all odds. These moments are hard-won, the result of years of effort by people who refuse to give up, no matter how fierce the current.

Training for the Impossible

Preparing for Escape from Alcatraz is a test of both mind and body. The swim is my greatest challenge; open water has always been my Achilles’ heel. To get ready, I’m logging time in the pool, seeking out cold water swims, and visualizing the leap from the ferry into the bay. I’m dialing in my bike fitness with long rides, hill repeats, and time on the trainer. The run—particularly the Sand Ladder—demands hill work and trail running to build the strength and grit I’ll need.

But the real training happens in the quiet moments, when doubt creeps in. When the pool is closed, when work piles up, when I question whether I have what it takes. It’s in these moments that I draw on the lessons of both the race course and the courtroom: keep moving forward, one stroke, one pedal, one step at a time.

Endurance, Justice, and Hope

Endurance sports and criminal justice reform are both about confronting the shadows—fear, fatigue, despair—and refusing to back down. They’re about believing in the possibility of change, even when the evidence is thin. They’re about community, too: the volunteers handing out water on the course, the advocates working behind the scenes, the friends and family who cheer us on.

As I look ahead to June 7 and my shot at the Escape from Alcatraz, I know that success isn’t guaranteed. The water will be cold, the hills steep, the sand unforgiving. But I’ll be there, alongside thousands of others, taking the leap. Because in the end, endurance isn’t just about crossing finish lines. It’s about never giving up, no matter how strong the current.

Whether I finish first, last, or somewhere in between, I’ll remember that every stroke, every mile, every act of advocacy matters. In the race, as in the work for justice, the real victory is in refusing to accept the impossible.

Until next time—Powder River and Peace.