On August 16, about 0930 Alaska daylight time, a tailwheel equipped Cessna 185 airplane, N8209U, sustained substantial damage during an off airport landing, about 15 miles northeast of McCarthy, Alaska. The airplane was being operated by Wrangell Mountain Air, Glennallen, Alaska, as a visual flight rules (VFR) passenger flight under Title 14, CFR Part 135, when the accident occurred. Visual meteorological conditions prevailed, and company flight following procedures were in effect. The commercial pilot and the three passengers were not injured. The flight departed McCarthy about 0900. During a telephone conversation with the National Transportation Safety Board (NTSB) investigator-in-charge (IIC) on August 18, the pilot said during the landing the right main landing gear wheel separated from the airplane. He said when the right gear leg dug into the ground the airplane spun to the right, the left wing struck the ground, and the airplane came to rest on its nose. The pilot said there were no known mechanical problems with the airplane prior to the accident, and that the airplane sustained substantial damage to the left wing. The pilot said the landing gear leg fractured at the top axle bolt holes. He said the landing gear leg had been inspected during the last 100 hour inspection.