A metal cutting insert (10) having a pair of cutting portions (10a, 10b) disposed on either end of a shank portion (10c), each cutting portion having a front clearance face (20), the upper boundary of which defines a cutting edge (14). A pair of spaced apart chip breaking surfaces (26a, 26b, 28a, 28b) commence at or near the cutting edge and extend away from the cutting edge. A pair of secondary chip breaking surfaces (44a, 44b, 46a, 46b, 48a, 48b, 50a, 50b) are located downstream of the first chip breaking surfaces and are interconnected with associated first chip breaking surfaces by transition surfaces. A center channel (30) is located between the chip breaking surfaces and includes an entry portion (30a). A tool holder (100) includes a base (102) and clamping arm (104) which together define a gap (106) for receiving one of the cutting portions of the insert.