Assuming I have every interest in using NaCl for all practical intents and purposes for a long time, assuming I have no interest in doing Matasano's crypto chal

Assuming I have every interest in using NaCl for all practical intents and purposes for a long time, assuming I have no interest in doing Matasano's crypto challenges, assuming I have a very healthy dosage of algebra, number theory, proof methods, and a sufficient general mathematical reading level, how do I go about learning crypto from the theory? If I raced with someone doing Matasano's challenges will I beat them? If I do, will I be able to practically implement better security systems by arguing for the value of 2010-era cryptography and motivating comprehensive reviews of the 80s era systems we already use?