The pilot reported that while enroute the “Warn Gear Unsafe” indicator illuminated and a decrease in airspeed was observed. After confirming that the airplane had enough fuel to reach the destination the pilot attempted to lower the landing gear. He placed the landing gear selector in the down position, but the landing gear position indicator lights were not illuminated. The pilot then followed the checklist for the emergency landing gear extension, but the gear indicator lights still did not illuminate, so he attempted multiple high G maneuvers to attempt to lock the landing gear to no avail. He then performed a low pass of the air traffic control tower who reported that the gear appeared to be down and locked. Upon touchdown the landing gear collapsed, and the airplane sustained substantial damage to the fuselage. Postaccident examination of the airplane revealed that the hydraulic system contained only trace amounts of fluid. The system was then serviced with hydraulic fluid and operated successfully. Further examination of the hydraulic system found that hydraulic fluid was leaking from a cracked fitting. Based on this information, it is likely that the inflight loss of hydraulic fluid through the cracked fitting resulted in the system failing to operate as intended.