On November 27, 1998, at 1345 central standard time, a Bellanca 7GCBC tailwheel equipped airplane, N5025C, groundlooped during the landing roll at the Stuttgart Municipal Airport, Stuttgart, Arkansas. The airplane, being flow by a private individual under Title 14 CFR Part 91, was owned by Tool Goose Flying Company, Tunica, Mississippi. The private pilot and the pilot rated passenger were not injured and the airplane sustained substantial damage. Visual meteorological conditions prevailed for the personal cross country flight that departed Tunica, Mississippi, at 1310. During personal telephone interviews, conducted by the investigator-in-charge, the pilot, passenger, and the airport manager reported the following information. The airplane landed in a 3 point attitude on the centerline of runway 18. During the landing roll with approximately 25 knots speed, the airplane veered to the right side of the runway. Application of the left rudder and the left brake by both occupants had no effect. Subsequently, the airplane departed the runway and groundlooped. The pilot and airport manager, who both examined the airplane, found structural damage to the fuselage and the left wing. The left main landing gear and propeller were also damaged. The airport manager reported that the left main wheel "rolled freely." The FAA inspector reported a separation of a left main landing gear bolt. The reason for the bolt separation was not determined. The pilot estimated that the failed bolt had accumulated 1302.2 flight hours since installation.