Shane McConkey's Last Run
Credit: Alfredo Martinez / Red Bull Content Pool

"Man, I miss Doug Coombs," McConkey told ESPN the Magazine in 2007. "When I found out he died doing the same stuff I do, it was a reality check. I think about him every time I'm in a dangerous situation. It's a reminder: Be careful."

McConkey was careful – meticulous to the point of neurotic, friends say. "Shane's one of those guys that's so talented you never expect something like this to happen," says Holmes. "He really thinks things through, and he has so much talent to fall back on. Nobody thinks Superman can die, you know?"

But when news of McConkey's death hit the mainstream media, the reaction was somewhat different: How could he not have died? And what was the risk taking for? A vicious debate broke out online between McConkey's fans and anonymous posters writing things like, "Sorry, but I don't feel sorry for him. He HAD to know that this sport would kill him someday; he just didn't know what day. When you get bored with life and push the envelope, your number will come up sooner than later."

But "bored with life" is hardly a phrase friends would use to describe Shane McConkey. And he was far from reckless: His stunts were the result of a decade of careful progression, beginning with skydiving in the late 1990s and including hundreds of BASE jumps, ski-BASEs, and wingsuit flights, each one carefully logged and analyzed. Holmes and others say Shane was the first to back out if conditions weren't right. He'd whittled the odds down as much as he could, but the odds caught up with him, as they do in blackjack. The house always wins.

"My mind goes to the people left behind," says film director Mark Obenhaus, who interviewed both McConkey and Coombs for the documentary Steep. "I saw these guys as heroic in some way; there's something amazing and wonderful about what they were doing. But gosh, there's been a lot of tragedy."

Says Glen Plake, whose 1980s ski movies inspired McConkey's career: "When people are passing away on a monthly basis, you gotta wonder: Have we gone too far here? Have we gotten to the point where the human body doesn't bounce that good after all?"

"Dude, this is a real kick to the soul for me," Miles Daisher says, looking up from his Red Bull parachute canopy, which lies bunched on the floor of his hotel room near Puget Sound. Normally energetic to the point of hyperactivity – he once BASE jumped 57 times in 24 hours, setting a world record – Daisher is somber and subdued. "Shane was my best friend," he says.

It's mid-April, barely three weeks after McConkey's death, and a few members of the Red Bull skydiving, paragliding, and BASE-jumping team – the Red Bull Air Force – have gathered at an airfield near Renton, Washington, for a few days of intensive free-fall practice. Shane was supposed to be here, too. He was a key member of the 12-flyer-strong Air Force, and arguably the most important: In 1998, before the Austrian energy drink even went on the market in the U.S., he became the first North American athlete Red Bull sponsored.

At the time, McConkey was known primarily as a skier, but he was beginning to get into BASE jumping. Daisher was living in the Trampoline House, a legendary Squaw ski-bum hangout that was also home to skier Kent Kreitler and an accomplished young BASE jumper named Frank Gambalie, who began teaching Miles and Shane his sport.

Though BASE jumping had been around for two decades, it was still very underground and experimental. Shorthand for "buildings, antennas, spans, Earth," BASE jumping boils down to leaping off cliffs or fixed, tall structures with a parachute. But whereas skydivers could rely on reserve chutes and long-established techniques from paratroopers, early BASE jumpers were essentially learning by trial and error – with "error" usually meaning death or serious injury. Jumpers would get tangled in their lines or caught by winds that slammed them into the cliff or structure from which they'd just jumped. As Daisher puts it, "In BASE jumping, you're constantly doing things to try and save your life."