A cutting pick comprises an elongate shank and a cutting tip mounted to one end of the shank. The cutting tip has a leading end, a trailing end and a mounting portion for mounting to the shank. The tip has a shape such that it diverges outwardly in a direction from the leading end to the trailing end to a portion of maximum diameter. An annular sleeve is attached about the shank adjacent to and in non-contacting relationship with the trailing end of the cutting tip. The maximum diameter of the cutting tip is of greater diameter than the diameter of the inner diameter of the annular sleeve so that the portion of maximum diameter overlies the sleeve radially.