A tool holder has a main body with a holder head extending away from a holder shank, the holder head having an insert receiving pocket at a forward end thereof, with a pocket support surface. A clamping member is retained in the holder head, the clamping member comprising a clamping shaft longitudinally extending along a shaft axis. A locking member operatively engages an abutment surface of the clamping shaft. The shaft axis does not intersect the pocket support surface, and the clamping shaft has a non-circular shape in a cross-section taken perpendicular to the shaft axis. The tool holder is configured to direct a clamping force towards, and clamp a cutting insert against, the pocket support surface.