Poly(alpha,L-glutamate)s carrying C-8, C-10, and C-12 fluorinated side chains were synthesized by polymerization of the corresponding amino acid N-carboxyanhydrides. Contact angle measurements with water were used to assess the effects of fluorination on the surface energies of films of the resulting polypeptides. The wettability of the polymers was found to decrease with increasing fluorine content, as expected. A remarkably high contact angle (121 degrees) was measured for the homopolymer carrying C-12 fluorinated side chains, indicating a surface consisting of closely packed trifluoromethyl groups. Side chain crystallization, consistent with the formation of such a surface, was suggested by the results of X-ray diffraction and calorimetric measurements.