A cutting tool assembly mounted on a rotating drum and having a base block, a wear sleeve and a cutting bit wherein a seal is located between the base block and wear sleeve is disclosed. A fluid passage spans from the rotating drum to a discharge location between the wear sleeve and the shank of the cutting bit. The fluid lubricates the shank of the cutting bit and bore of the wear sleeve allowing the cutting bit to rotate freely within the wear sleeve. Rotation of the cutting bit promotes even wear and long life of the bit.