On June 19, 1998, about 1914 Alaska daylight time, a tundra tire and tail wheel equipped Cessna 185E airplane, N85CF, sustained substantial damage while landing at Merrill Field, Anchorage, Alaska. The airplane was being operated as a visual flight rules (VFR) cross-country personal flight when the accident occurred. The airplane was registered to, and operated by the pilot. The certificated private pilot, and the sole passenger, were not injured. Visual meteorological conditions prevailed. The flight originated at the Talkeetna Airport, Talkeetna, Alaska, about 1845. During a telephone conversation with the National Transportation Safety Board (NTSB) investigator-in-charge (IIC), on June 19, 1998, at 1940, the pilot reported he landed on runway 15 at Merrill Field. The runway surface was dry asphalt. During the landing roll, the right tire deflated. The airplane veered to the right, and the right wing tip struck the runway. The airplane began to ground loop, and the pilot applied the brakes. The airplane nosed down, coming to rest in a near vertical attitude. The airplane received damage to the propeller, engine cowling, firewall, and right wing tip. A Federal Aviation Administration (FAA) airworthiness inspector, Anchorage Flight Standards District Office (FSDO), reported he examined the airplane's right main tire. The inspector noted that the tire tube valve stem was broken, and the right tire deflated. The 24 inch tundra tire wheel adapter displayed scuffing on the outboard half of the wheel. The main wheel half was not damaged.