A milling system for a milling machine includes at least one cutting assembly configured to be coupled to a drum. Each of the cutting assemblies includes a base portion and an impact portion. The base portion includes a standoff coupled to the drum, a first base block coupled to the standoff, and a second base block coupled to the standoff at a position upstream of the first base block in a direction of rotation of the drum and at angle from the first base block. The impact portion includes a cutting bit and a tool holder coupled to the first base block, and a protective element coupled to the second base block.