It’s a bright winter morning and Bob Coomber, better known as , is taking it slow up a trail in , near Oakland, California. His gloved hands keep tireless pace with each other on the wheels of his wheelchair. His long, sinewy arms tense and twist in response to every crest, every divot of the trail. As we hike, Coomber admits he hasn’t been out in this chair—a specially modified all-terrain wheelchair—for more than three years. “It’s been on the back porch,” he says, “just sort of tempting me.”

In just a few months’ time, however, Coomber will be in prime condition. He has to be: This fall, Coomber will make his third attempt to take his chair up and over the 11,845-foot in California’s southern Sierra Nevada, west of the town of Independence. The trek will take him from the trailhead to Kings Canyon, on the other side of the pass, for a round-trip of approximately 24 miles. Depending on the incline and the weather, Coomber will travel anywhere from half a mile to a few miles per day. The journey, he estimates, will take him 10 to 14 twelve-hour days of near-constant exertion. If he succeeds, Coomber will be the first person in a wheelchair to cross the Sierra.

First by foot, then by wheel, Coomber has spent much of his 63 years on this earth . As a kid growing up in Piedmont, California, he was active and athletic. In high school, he played basketball and baseball and ran a brisk 4:35 mile for his track team. In his free time, Coomber would spend hours, days, in parks across the Bay Area. And on vacations in the Sierra, he would hike to peaks where no trail had yet been forged, just to get to the top of something magnificent.

Then, when Coomber was 20 years old, just as he was launching into a career with the Oakland Police Department, he was diagnosed with Type 1 diabetes. The disease attacked Coomber’s system with unbridled aggression: It shaved dozens of pounds off his frame and sapped him of his energy. Due to the severity of his symptoms, Coomber had to leave the force after just three years.

Several years later, in 1990, Coomber was hiking with his family around Lake Almanor, a few hours north of Sacramento in Plumas County, when he heard a gruesome crack and fell to the ground. His left leg had shattered into what he says felt like a thousand pieces. Complications with his diabetes, he learned, had resulted in a crippling form of osteoporosis. Seven breaks—in his legs, ankles, and knees—followed. Coomber was soon faced with his best, and perhaps only, option: a wheelchair.

When Coomber gives motivational talks—which he does occasionally at events such as the Abilities Expo—he takes care to emphasize that summiting mountains isn’t a hobby he picked up overnight. It’s something that has taken stubbornness, a trusty sidekick in the form of a battered, bare-bones chair, a hell of a lot of focus, and a few decades of painful trial and error. Coomber tries to make this point, but not everyone will believe him. After five minutes in his presence, you probably wouldn’t either.

Coomber has a strategy for practically every puzzle the trail presents to his chair. He reads the road no more than ten feet at a time; he straddles the low points and, to avoid catching his smaller front tires, wheelies over nasty boulders and down jagged slopes. Still, all it takes is a deceptive root or a misread on a grade and disaster can raise its ugly head. In 2015, while competing in a 5K in Livermore, California, Coomber ran over a rock. His chair was stopped dead and his body thrown forward, breaking his femur. “File it under ‘shit happens,’” he says now.

Hiking with Coomber, you forget that the man next to you is constantly gauging angle, traction, and weight distribution. Every move he makes in the chair seems somehow spontaneous, executed with a cowboy’s grace. “I always look for the most level way to get around to not get tippy,” he says. We are at a dip in the path, a steep slope off to our left. “Sometimes, when you get tippy and you don’t expect it, you get on your side in the dirt. Which is really like, what are they going to do to you? Put you in a wheelchair? No big deal.”

Coomber has been breaking records for more than a decade. On August 24, 2007, he became the first person in a wheelchair to summit the 14,246-foot White Mountain, California’s third-highest peak. Shortly after that, he became the first wheelchair hiker to reach the peaks of Mount Diablo and North Peak, both in the Diablo Range, as well as Mission Peak in Fremont and Sonora Peak in the central Sierra. In 2007, Coomber was inducted into the . In 2008, he received the . When the local reporters are having a slow week, they give 4WheelBob a call to see what crazy thing he’s up to next.

But for the past five years, the answer has remained the same: Kearsarge Pass.

Coomber’s first attempt to cross the pass was in September 2013. He began the trek in high spirits. He joked with passing hikers. He squinted lovingly at the mountains, and he struck up his customary good-natured, though profanity-laden, rapport with his chair. Tal Skloot, the documentarian who followed Coomber for his film , captured this optimism. He also captured the more spectacular feats of Coomber’s ingenuity. When the path grew too narrow for his wheelchair, Coomber would swing himself onto nearby boulders to lift the chair up and over the roadblock. “All that, as I’m fond of saying, for two feet,” Coomber quips to the camera.

The first stretch of the Kearsarge Pass Trail is unforgiving: ragged switchbacks and little shade. Half a mile from the trailhead—a distance that took Coomber nearly five hours to cover—he became woozy. Recognizing the symptom, he stopped and pricked his arm to test his blood. The reading came back with a devastatingly high 500 mg/dL. Several minutes later, when the level still hadn’t dropped, Coomber clawed at the tubes of the insulin pump attached to his stomach. The transfusion section of the pump had bent forward. He wasn’t receiving a single drop of insulin. The third time he tested above 500 mg/dL, Coomber turned around, face set in a mask of discomfort and disappointment. He spent the night in a hospital bed in Bishop, scheming how to get back to Kearsarge as soon as possible.

On Coomber’s second attempt, in September 2014, he made it three days into the hike before he met his foil. The boulder field on the Kearsarge Pass Trail is a brutish landscape of heavy rocks that sprawl haphazardly across the path. Faced with this, Coomber tied a thin rope around his shoulders and looped it over the back of his chair. With his legs thrown before him, he began to drag himself and his chair backwards through the piles of rocks, his arms straining and his mouth cursing.

Eventually, Coomber slowed to a stop. A blister that had formed on his thumb was near the point of infection. The path was too rocky and his method too laborious. When he decided, once more, to turn around, Coomber was a mere 1.5 miles from the top of the pass. The next four days he spent in a Bay Area ICU, suffering from a condition called diabetic ketoacidosis, meaning he had low insulin and a buildup of acids in his bloodstream.

And yet Coomber is convinced this year will be a success. When I join him in the Oakland Hills, Coomber is keeping up a running commentary about bird songs, native plants, and dogs. Coomber tells me that he sees his first two attempts at Kearsarge more as stepping-stones than roadblocks. “It’s my own test,” he says. “If I don’t finish something, that doesn’t make it a failure. If I don’t make it, then I know what to train for the next time.”

In the coming months, Coomber will spend much of his free time—what’s not allotted to his role as council member in Livermore or to watching the Golden State Warriors on TV—training. In the gym, he applies himself to developing his shoulders, middle and lower back, deltoids, trapezius, and triceps. One of his techniques is to tow 45-pound weights behind him back and forth across the gym floor. For endurance, he chooses flat, paved trails—like the 64-mile round-trip of the Iron Horse Regional Trail between Concord and Pleasanton—that can keep him occupied until far after dark. His wife, Gina, tracks these long days with an app connected to Coomber’s Spot tracker. Although, as Coomber says, “She knows I may be out there almost overnight. I may not come back.”

Coomber tells me that, for his next attempt at Kearsarge, timing is everything. The sweet spot is late summer or early fall, when the snow has cleared and the chances of a rogue flurry are the lowest of the year. Before he goes, Coomber will consult his doctors to map out possible problems with his blood sugar levels. For the boulder field, he will employ the help of a pack horse or two. He hasn’t yet found a cure for those vicious blisters, but as far as Coomber is concerned, they’re just part of the challenge.

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