On August 25, 2016, about 1300 mountain daylight time (MDT), a Piper PA-18-180 airplane, N66898, departed the left side of the runway on landing at United States Air Force Academy Airfield (AFF), Colorado Springs, Colorado. The airplane sustained substantial damage to the right wing. The airline transport rated pilot, the sole occupant, was not injured. The airplane was registered to Big Q Aviation Corporation and operated under the provisions of Title 14 Code of Federal Regulations Part 91 as a glider towing operation. Visual meteorological conditions prevailed for the flight, and no flight plan was filed. The pilot reported that he just completed a local glider towing operation and was landing on runway 16L. After a routine touchdown and roll out, there was a "large gust of wind" from the right side that lifted the right wing of the airplane. To "regain directional control," the pilot applied rudder, slowly lowered the tailwheel to the ground, and applied pressure to both wheel brakes. He stated that when he applied both wheel brakes, the left brake grabbed "more efficiently" than the right brake and the airplane turned to left and exited the runway. The airplane rotated counterclockwise and the right wheel dug into the soft dirt, and subsequently, the right wing contacted the ground. The pilot stated that when he began his shift that day, he was advised there "were issues with the steering of the tailwheel." An inspection of the tailwheel by the responding Federal Aviation Administration inspector noted the tailwheel functioned properly.