On April 16, 2009, approximately 1320 Pacific daylight time, a tail wheel equipped Maule M-5-235C airplane, N9219E, sustained substantial damage during the landing roll and subsequent ground loop at Whiteman Airport (WHP), Los Angeles, California. The airline transport pilot was not injured, and his private pilot-rated passenger received minor injuries. The passenger/owner was operating the airplane under the provisions of 14 Code of Federal Regulations Part 91. Visual meteorological conditions prevailed for the cross-country check ride, which had originated from Santa Paula, California, about 1300. A flight plan had not been filed. The airline transport pilot, who was a Federal Aviation Administration (FAA) inspector, reported that he was giving a check ride to the passenger, which the passenger had successfully completed. On the return flight to their airport of origination, the passenger asked him if he would like to fly the airplane. The FAA inspector took control of the airplane (becoming the pilot-in-command) and entered the traffic pattern for a full stop landing. The landing was made on runway 30, a 4,120-foot-long and 75-foot-wide asphalt runway. The pilot stated that the Automated Terminal Information Service (ATIS) reported the wind at 230 degrees at 10 knots. The pilot noted that while on final approach, very little crosswind correction was necessary to maintain the runway's centerline. On touchdown, the airplane bounced and touched down a second time in a three-point landing. A couple of seconds later, during the landing roll, the airplane began to weathervane to the left. The pilot stated that his initial right rudder input was insufficient and he applied full right rudder and more left aileron. The airplane abruptly turned to the right and departed the runway at about a 45-degree angle. The airplane began skidding sideways in the dirt, the left main landing gear failed inward, and the left wing tip impacted the ground. The reported wind at Whiteman Airport at 1247 was from 230 degrees as 10 knots, which agrees with the pilot's report. Using this wind, the crosswind component for the landing was calculated to be a 9-knot left crosswind component. Post accident examination of the airplane by an FAA inspector revealed structural damage to the left wing and left horizontal stabilizer. The examination found no evidence of mechanical failures or malfunctions that would have contributed to a loss of directional control.