On August 3, 1996, at 1512 mountain daylight time, a Cessna 210, N414N, landed with the landing gear in the trail position at Pueblo, Colorado. The private pilot and his passenger were not injured and the aircraft sustained substantial damage. The flight was operating under Title 14 CFR Part 91 and a VFR flight plan was filed. This personal flight departed La Junta, Colorado, at 1330, with an intended destination of Sterling, Colorado. According to the pilot, when the landing gear was raised after takeoff from La Junta, the gear failed to fully retract and it would not return to the down and locked position. The pilot said after attempting to lock the landing gear down by normal and emergency methods and radio discussion with ground facilities and air traffic control, he decided to proceed to Pueblo, Colorado, where there was long, hard surfaced runways, and adequate emergency services. After a fly by to confirm the landing gear configuration, a precautionary landing was performed on runway 35 with the landing gear in the trail position. During the landing slide, damage was sustained to the empennage, right wing, right horizontal stabilizer, and gear doors. The aircraft was examined by an FAA airworthiness inspector. According to his findings, the nose landing gear was chaffing on a hydraulic line and when the landing gear was raised, a leak in the line depleted the hydraulic fluid by pumping it overboard. Attempting to lower the landing further depleted the fluid and attempting to "pump" the landing gear down by the emergency hand pump emptied the sump. Schematic drawings and trouble shooting pages supplied by Cessna confirmed the reason for the fluid depletion. Improper routing of the hydraulic line allowed the line to chafe on the nose wheel. When the line was routed improperly is unknown. According to the pilot, both he and his passenger attempted to "push" the main landing gear to the down and locked position using the tow bar without success.