Prior to the introduction of modern computer ciphers such as Blowfish and RSA, societies resorted to the preeminent and complex hand ciphers of their millenia. Hence, having a deep understanding of the mathematical background and historical origins of these ciphers grants us a comprehensive view of the current state and future of cryptography. To grasp the aforementioned understanding, the research will aim to describe, analyze, and program a variety of Transposition Ciphers, Substitution Ciphers, Block Ciphers, and introductory Stream Ciphers: each will include a description of the cipher’s history, encryption and decryption method, and a mathematical analysis, which includes its vulnerabilities and cracking methodologies. This analysis will not only broaden one's understanding of the roots of modern cryptography, but also give one a comprehensive look at its significance in present-day society. Through this extensive research, the overall goal would be to detail the construction of an open-source utility with the capability of encrypting, decrypting, and cracking the previously mentioned ciphers.