The microstructual changes and strengthening behavior of pearlitic steel during cold drawing has been investigated. The strengthening behavior of pearlite concided with Embury-Fisher`s model with Hall-Petch constant, 1.9㎏/㎜^(372). The observed crack initiations were classified into two group. The crack initiation by necking of cementite was observed at the cementites aligned to the drawing direction. The other crack initiation was observed at the massive and round cementite particles. It could be explained by the behavior of cementite aligned perpendicular to the drawing direction. With increasing strains, the distance between buckled cementite plates were narrowed and the tip of buckled area formed massive and round cementite particles.