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Leary was widely regarded as one of the most talented Yosemite climbers of his generation. He had climbed El Capitan dozens of times and set the speed record for climbing the Salathé Wall, with Alex Honnold, in 2009. He also set a new speed record on the Nose, with Dean Potter, in 2010 (broken in 2012 by Hans Florine and Honnold). That same year, he climbed three El Capitan routes in a day with Honnold. In 2012, he and Mayan Smith-Gobat set the mixed male-female speed record for the Nose.
