A tool holder is disclosed for use with a milling drum. The tool holder may have a cylindrical body defining a first end and a second end, the first end configured to be received within a tool mounting block of the milling drum, the second end configured to receive a cutting bit. A flange may be located between the first and second end with respect to an axial direction, and a first bore, with a first opening defined by the second end and extending towards the first end. A frustoconical portion may be located between the flange and the first end with respect to the axial direction and a cylindrical portion located between the flange and the first end. At least one radial opening may pass through at least the wall of the cylindrical portion to intersect or be open to the first bore.