On May 4, 2019, about 1146 mountain daylight time, a Cessna A185F, N185FT, sustained substantial when it was involved in an accident at Glacier Park International Airport (GPI), Kalispell, Montana. The pilot and the pilot-rated passenger were not injured. The airplane was operated under the provisions of Title 14 Code of Federal Regulations Part 91 as a personal flight. According to the pilot, while landing at Ferndale Airport (53U), Bigfork, Montana, in light and variable wind conditions, the tailwheel-equipped airplane pulled to the right as it slowed. He accomplished a full stop landing and taxied back to take off. The pilot stated that the takeoff was uneventful, and he remained at 53U for another landing pattern. During the second landing, the airplane pulled hard to the right as it slowed, which prompted the pilot to initiate a balked landing; he elected to return to GPI where the flight had originated earlier that day. The pilot stated that the wind was reported at 210° magnetic at 5 knots at GPI. The landing on runway 20 was normal, on centerline, and with the tailwheel lock engaged. However, shortly after touching down, he lost control of the airplane, and it veered off the right side of the runway, despite his left rudder inputs. The pilot believed there was an issue with the tailwheel. He stated that the airplane came to rest about halfway down and 10 ft off the edge of the runway. Postaccident examination of the airplane revealed substantial damage to the left wing. The airplane was further examined by an airframe and powerplant mechanic under the oversight of a Federal Aviation Administration inspector. The tailwheel and flight control system, including the rudder system, were examined. It was noted the tailwheel would turn right freely and “break free” normally. The tailwheel would only turn left about 15° and would not break free. It could not be determined if the anomaly with the tailwheel was present before the accident or resulted from the accident.