09/10.19 OUTSIDE MAGAZINE 59
O’Brady with
his business
manager (and
wife) Jenna
BesawEileen Brady, who bestowed a blended sur-
name on both him and his elder sister, Cait-
lin. A dozen family friends were present for
his home birth, which happened on a futon
while Bob Marley played on repeat.
The family, poor but comfortable, moved
to southeast Portland when O’Brady was
nine months old, and early on it became
clear that he possessed extraordinary ath-
letic ability. He scored so many goals as a
young soccer player that his coaches had to
stress “the value of the assist,” according to
his mom. He won his first state swimming
championship at age eight. When he was
in high school, Yale recruited him to swim
breaststroke. “I was so clueless when they
called with an offer,” he says. “I was like,
Yale, where is that?” At one point, he was
ranked fifth in the U.S. for his age group in
the 200-yard breaststroke, not far behind
Michael Phelps.
In 2008, his life took a dramatic and hor-
rific turn. A little over a year after graduat-
ing with a degree in economics, O’Brady was
on a tour of Pacific surf breaks. He met up in
Thailand with David Boyer, his best friend
from childhood, so they could learn to scuba
dive on the island of Ko Tao. One evening on
the beach, a few local guys came out with a
rope soaked in kerosene, lit it, and started
twirling it to make a flaming jump rope, a
strange but popular pastime at backpacker
parties in Thailand.
Boyer went first, the rope hissing in the
tropical air as it circled above him. O’Brady
jumped in but mistimed his leap and landed
straddling the rope. Flaming kerosene splat-
tered up over his torso and neck; the rope got
tangled around his legs and burned them
badly. O’Brady collapsed into the sand and
freed himself, burning his right hand, then
ran to the sea and dove in.
“Salt water on a wound like that is the
most excruciating pain you can imagine,” he
recalls. “I got out and looked down, and the
skin on my legs was charred and peeling like
a hot dog.”
O’Brady spent three months convalesc-
ing, first in a grimy rural clinic, then at a
hospital on the more developed island of Ko
Samui, where he endured eight surgeries as
doctors cut away dead flesh and debrided
the deep second-degree burns that had ex-
posed nerves on a quarter of his body. They
weren’t sure he would ever walk normally
again, given how scar tissue contracts.
When O’Brady takes the stage during
lunchtime at the Riverhouse, he tells his
story masterfully. Pacing back and forth in
front of a large screen and wearing a lapel
mic, he lingers on the key moments that un-
derlie his hero’s journey. When he describes
his accident, the audience is visibly moved.
A woman near the front puts her hand over
her mouth. A man toward the back squints
and looks away from the stage.
O’Brady tells the crowd that the mishap,
and his dashed future as an athlete, sent
him into depression. His mother, sitting by
his hospital bed, told him to set a goal for
himself:“Life’s not over, Colin. What do you
want to do when you get out of here?”
“Life’s over, Mom.”
“Just visualize something.”
He saw himself completing a triathlon.
“That wasn’t something I’d ever done in
my life, but I started training right then,” he
tells the audience. A picture of him doing
dumbbell presses while bandaged in a Thai
hospital bed flashes on the screen. Thecrowd roars with laughter.
Months after the accident, back in Port-
land, he took a step, then five, then ten. He got
a job as a commodities trader in Illinois. A
year and a half after the accident, he crossed
the finish line of the Chicago Triathlon. Four
hours later, he checked the amateur results.
He’d won.AT THIS POINT, the story of Colin O’Brady
takes off in a rocking montage. Imagine
it set to any track on Graceland, one of
his favorite albums. He quits his job and
becomes a professional triathlete, backed by
a benefactor who believes in him. He races in
31 events in 25 countries on six continents.
He shares hotel rooms with other athletes
in Australia and China. Over four years, he
has seven top-ten finishes, placing fourth in
Zimbabwe. Often he has the love of his life at
his side. He’d met Jenna Besaw in Fiji a couple
of months before the rope accident. She was
20, on spring break while studying abroad
in Australia. They kept in touch during his
recovery, and in 2010 she moved to Portland
to live with him. In 2014, O’Brady proposed
atop Ecuador’s third-highest peak, 18,996-
foot Cayambe.
A few days after the conference at the Riv-
erhouse, I meet the couple in Jackson, Wyo-
ming, where they plan to spend half their
time. It’s cool and wet outside, the Tetons
hidden in clouds. Besaw, who has long brown
hair and an athletic build, opens the door of
their modest red townhome, which sits on
a quiet street near Snow King, the local ski
area. They’re still moving in, and the couch
just arrived. A small painting of O’Brady in
Antarctica, a gift from a fan, hangs near the
kitchen. Their goofy wheaten terrier, Jack,
toddles over to have his haunches scratched.
Every morning they take Jack for a steep
hike up the ski slopes, and today I’m sweating
profusely as I try to keep up. “Tell him what
you’re training for,” O’Brady says to Jenna as
we punch up blotches of late-spring snow.
She hesitates. “It’s Everest,” O’Brady says.
Besaw studied international relations but
is a naturally talented marketer with a sharp
mind for business and communications. In
2012, when Eileen Brady ran an unsuccessful
but spirited campaign to become Portland’s
mayor—one of her TV ads, called “Put a
Job on It,” parodied Portlandia—she asked
Besaw to be a key member of her staff. In the
early days of his triathlon career, O’Brady
made Besaw his manager. She quickly re-
alized that his athleticism wasn’t his only
valuable asset. Looking around at races, she
noticed that a number of competitors with
little chance of reaching the podium had
sponsors, usually because something about
them appealed to a particular audience.