The uncertificated pilot reported that while on a cross-country flight in his tailwheel-equipped airplane, he stopped along the way for fuel, and during that landing, he noticed that the right main landing gear felt “mushy.” However, he elected to depart and continue the flight to the destination airport. While landing on the dry, paved runway, which required a correction for strong, gusting crosswind conditions, the left main landing gear wheel touched down first, then the right main landing gear wheel touched down. The pilot said as the weight of the airplane transferred to the right main landing gear, the right oleo strut “mushed out.” The airplane subsequently ground looped to the left, and the right main landing gear collapsed. The airplane sustained substantial damage to the right wing and fuselage. The pilot reported that before leaving on the accident flight, he had observed red fluid leaking from the right landing gear oleo strut assembly, and that the airplane had not flown for most of the year. A review of maintenance records revealed the last annual inspection of the airplane was nine years prior to the accident. According to FAA records, the pilot did not possess a pilot’s certificate. Other than the leaking oleo strut, the pilot reported that there were no preaccident mechanical malfunctions or failures with the airplane that would have precluded normal operation.