Trailer towing hookup questions

We pulled a 19 ft Featherlite enclosed with a 96 1500 360 for several years. Always ran with overdrive off, but at 70 mph on the interstates it would sway radically when you would get in the ruts the rigs cause. We ended up losing a spindle and wheel due to this 11 miles out from Carlisle. That weekend, the sway control setup was on- huge difference in the way the truck rode and the amount of control it gave. Not long after that , my buddy was towing his pro street Dart on the highway, caught the edge the wrong way and ended up totaling his car. All it takes is once. A little prevention can save your life