A rolling container assembly includes a base container, wheels to provide rolling support, at least one removable container, and a container engaging region with an automatic lock interacting between the removable container and the container engaging region. The automatic lock is releasable so that the removable container can be released to enable the at least one removable container to be carried by its carrying handle and transported separately from the base container. The assembly has a lower drawer and an upper drawer, and a slide structure having a first portion mounted to the upper drawer and a second portion mounted to the lower drawer to facilitate movement of the drawers. The lower drawer and upper drawer are independently movable between their respective open and closed positions. The apparatus includes a central frame structure carrying a lock member that enables the upper drawer to be locked in the closed position.