Abstract: A cutting head rotatable about a first axis, comprising an intermediate portion and a tip portion. The intermediate portion has a plurality of leading edges defining a cutting diameter, and the tip portion has an axially forwardmost tip point and a plurality of front surfaces with outer and inner cutting edges. An outer rake surface adjacent to each outer cutting edge has a positive outer rake angle, and an inner rake surface adjacent to each inner cutting edge has a negative inner rake angle. Each outer rake surface is disposed on a head flute intersecting one of the leading edges, and each inner rake surface is disposed on a gash intersecting one of the head flutes. Each gash extends to a gash path end point located a first distance axially rearward of the tip point, and the first distance is greater than thirty percent of the cutting diameter.