In one aspect of the invention, a degradation assembly has a holder attached to a driving mechanism and comprising a longitudinal central bore. The bore has an opening at a distal end from the driving mechanism. The pick has a body intermediate a shank and an impact tip, the shank being disposed in the central bore of the holder and the body extending from the opening of the bore. The impact tip has a diamond surface. The degradation assembly also has a lubrication mechanism adapted to apply lubrication to the shank.