An agricultural caddy assembly and agricultural trailer are provided. The agricultural caddy assembly includes a wheel attachment member, a tractor-tool attachment frame, and a bolster for rotatably connecting the wheel attachment member to the tractor-tool attachment frame. The agricultural trailer includes a tractor hitch, a tool frame, a wheel attachment member, a tractor-tool attachment frame connected to the tractor hitch and the tool frame, and a bolster for rotatably connecting the wheel attachment member to the tractor-tool attachment frame.