Whether tackling the Dipsea Race, researching cancer treatment or creating short films, Patrick “Paddy” O’Leary is always pushing boundaries and inspiring others. In 2023, at age 35, the oncologist, film producer and former national Ireland Lacrosse player won the 112th running of the Dipsea Race. The Dipsea Race is 7.4 miles and the oldest trail race in America; he won with a time of 47:23. The year before, he placed second.

“When I moved to San Francisco in 2013 at the age of 25, I found my way back into running through the Marin and San Francisco trail running community,” O’Leary said. “The San Francisco Running Company had big group runs, so I joined them and fell in love with trail running. Then, I realized that [I was good] enough at [running to make something of it], and it kind of snowballed from there.”

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Growing up in Dublin, Ireland, O’Leary began running at a young age because his dad was a runner and a cross-country coach. In his college years and up until his 20s, he played for the Irish national lacrosse team, where he had a successful career. Later, he switched gears to full-time trail running when he moved to the United States for a postdoctoral research position at the University of California, San Francisco. For several years, O’Leary attempted to get a spot in the Dipsea race, which is a lottery system. But it took him until 2019, which ended up being one of his favorite races ever.

“[In my first race,] I had 1400 people ahead of me. [I thought to myself,] ‘How are you going to pass all these people when there’s traffic, a single track and poison oak everywhere? How are you gonna catch everyone?’ But I ended up passing like 900 people, came in 499th and won the runner section. It was the proudest top 500 position I’ve ever had,” O’Leary said.

After running the Dipsea four times, he plans to take on the course again this year on June 8.

“[My first Dipsea] made me fall in love with the race: the chaos of it, getting to run with 8-year-olds up to 80-year-olds, men and women and everyone competing. It’s a really fun event. The [entire] community comes in behind [you], like when you go up and crest over Cardiac Hill, the energy up there and at the finish line is unparalleled,” O’Leary said.

Senior cross-country and track athlete Marley Nacco has run the Dipsea seven times and is inspired by O’Leary’s drive and athletic ability.

“He is the definition of a Dipsea runner: super determined, positive and humble. I wouldn’t want anybody else to win the Dipsea because he is so deserving of it. He’s a great guy, and he’s so upbeat,” Nacco said. “My favorite part of the Dipsea is getting passed by him.”

O’Leary ran in the Invitational section of the race the year he won, so due to the staggered start times for each group, he passed people of all ages. 

“The year I ended up winning [the Dipsea], I went out irresponsibly fast at the start and was on the edge of maybe going too fast, blowing up completely, and having to walk the rest of it. I think I [walked] that line perfectly, [though]; I think that gave me the advantage,” O’Leary said.

The Dipsea Race is capped at 1,500 runners and has no age requirements. Many Redwood students participate, whether running or hiking the race or completing the trail on their own time. According to the March Bark survey, 65 percent of Redwood students would be interested in running or walking the Dipsea race once in their lives.

“It’s a really hard race, but the environment is super upbeat and joyful, and everyone is so positive. It’s seven miles of everybody working together, even though it is a race,” Nacco said.

Not only does O’Leary crush the Dipsea, but he has also qualified for the Irish Mountain Running team in three world championships. 

“In 2015, I started doing Ultra races, competitive shorter trail races and my first marathon. In 2016, I started to run with the North Face, and then two years later, I qualified for the Irish team, so I got to do my first World Championships. I have been fortunate to compete in three World Championships: in Spain (2018), in Argentina (2019) and in Thailand (2022). This year, I’m going to do the trials for the team and then hopefully qualify for the World Championships in the Pyrenees in September,” O’Leary said.

Sophomore cross-country and track athlete Justin Shern has run the Dipsea Race three times and is a fan of O’Leary.

“I remember when he passed me; it was honestly kind of amazing just to see how strong he was. He was running impressively fast while we were still going uphill,” Shern said. “From [his] speech and just seeing the way he held himself after the race, he seemed humble, super nice and [like] a great guy. That’s why he’s part of the Dipsea running community and the running community here in Marin as well.”