A roll off trailer includes first and second trolley assemblies and a hoisting cable connected at one end to the first trolley assemble and extending about a sheave in each of the first and second trolley assemblies. The cable connects to a container. The second trolley is displaced t in a first direction while simultaneously drawing the container via the cable from the first grounded container to a second container position generally midway atop the trailer. Then, the first trolley is displaced in a second direction while simultaneously drawing the container via the cable from the second container position to a third container position generally adjacent the front of the trailer.