"We nailed the Sassongher Line today!" screamed the header of Shane McConkey's March 25th blog entry.

Though McConkey, 39, was best known as one of the most inventive skiers of the past 20 years, this particular line interested him for reasons beyond skiing. For more than a decade, he'd been an avid BASE jumper, and here in the Italian Dolomites, on an icy, 45-degree chute on the 8,612-foot Sassongher, he'd found the perfect place to bring his two passions together by pulling off a picturesque ski-BASE. He'd arrived a few days earlier with pro skier and fellow BASE jumper J.T. Holmes, 29, and a four-man film crew from MSP Films (Matchstick Productions). The group headed for the Val Scura couloir, on Sassongher, to explore a feature that only someone like McConkey could get excited about. "About 1/3 of the way down the couloir there is a ramp that slopes up and out to the right," he'd written. "It leads out to a nice field of snow above about a 1,000 foot cliff."

McConkey went first, skidding three or four turns on the firm snow before throwing a big front flip off the cliff, free-falling for a few seconds, deploying his parachute, and gliding down to the snow-covered valley floor. Thirty seconds after he landed, Holmes, who'd straight-lined the snowfield above, flew off the cliff, eventually joining him below. "Today was a good day!" McConkey blogged.

Drawn to parachuting by an innate love of flight, McConkey began skydiving in 1995 and did his first BASE jump in late 1996. He and one of his best friends, Miles Daisher, were being mentored by BASE pioneer Frank Gambalie when, in 1999, Gambalie drowned after he landed a successful but illegal jump off Yosemite's El Capitan and tried to swim across the swollen Merced River to evade park rangers. Their apprenticeship cut short, McConkey and Daisher completed their education together, each filling in the blanks in the other's knowledge. McConkey went on to make more than 700 jumps and thrived on pushing the sport into new territory. He introduced his friend Holmes to BASE in 2002; the following winter, inspired by the Austrian ski-chase scene in the James Bond film The Spy Who Loved Me, which ends with a stuntman skiing off a cliff and pulling his parachute, McConkey and Holmes did their first ski-BASE together off a 400-foot cliff at Lover's Leap, near South Lake Tahoe.

Even as the ambition of their ski-BASE jumps progressed and they used their new skills to explore previously unskiable lines—the two ski-BASEd off the Eiger in 2004—they were chafing against the limitations skis imposed on their jumping. "We plateaued with our tricks and our ability to free-fall with skis on," says Holmes, "so we got to a point where it was like, We're going to ski off and do a few flips, but then what?"

Enter the wingsuit, a jumpsuit with fabric pouches sewn into the armpits and between the legs. In the air, the whole suit inflates, turning the flier into a human wing. In February 2007, on a 3,000-foot cliff in Norway, McConkey and Holmes each performed three successful wingsuit ski-BASE jumps, in which they skied off the cliff, released their skis, and flew for about 40 seconds before opening their parachutes. It was the first time such a stunt had ever been attempted. Convinced they were on to something, they returned to Norway that summer, along with Daisher and an MSP film crew, to hone their flying skills. "The wingsuit is the closest thing to nonpowered human flight you can get," McConkey explained in Focused, the resulting MSP segment.

A year later, McConkey went to Italy to BASE-jump in the Dolomites and deemed their jagged peaks and spires the perfect place to push the evolution of ski-BASE once again. This January, he e-mailed MSP and one of his main sponsors, Red Bull. "I have had some goals for quite some time now and would like to make them happen," he wrote, proposing a March trip and including a detailed itinerary, photos of his target cliffs, and an outline of his goals, the first of which, ski-BASEing off a classic line, they accomplished on Sassongher. His second goal was to do more wingsuit ski-BASE jumps. The third and most audacious goal was to attempt a "double-stager" ski-BASE, in which he and Holmes would ski-BASE off one cliff, land on their skis, cut away the first parachute, and then ski off a second cliff, using a second parachute to reach the ground.

"The double-stager was the new next thing, and Shane was all about the new next thing," says Steve Winter, one of the founders of MSP, who was heading the film crew in Italy. "He's always thinking ahead."

After a few days of scouting, completing the Sassongher jump, and a day off due to bad weather, Holmes, McConkey, and their local guide got on the Sass Pordoi cable car the morning of March 26. They spent an hour and a half studying a cliff they thought might work for a later attempt at a double-stager. At 11:30 A.M., they had coffee at the top of the cable-car line and decided to try a wingsuit ski-BASE from a spot on Sass Pordoi where McConkey had jumped the previous summer and that he and Winter had scouted from a helicopter a few days prior.

From the top of the cable car, they skied partway down a narrow gap between two cliffs before traversing out, skier's right, to a steep snowfield bounded by sheer rock faces above and below. They put their skis on their backs, donned crampons and ice axes for the traverse, and arrived at their chosen cliff at about 1:30 P.M., staring over the edge toward the broad valley 1,500 feet below.