Books focusing on Sigmund Freud are voluminous; dedicated scholars have spent their lives combing through every detail of his life and contributions, and controversies surrounding his relationships with his followers, colleagues, and patients. However, there has been very little focus on his addiction to cocaine. Even less attention has been paid to his dependence to cigars, which persisted despite the development of oral cancer and numerous surgeries. This chapter focuses on his life vis-à-vis these highly addictive and dangerous substances, discussing their significance in the context of his personality, childhood experiences, and career trajectories. The main purpose of the chapter is to use this dimension of his life to highlight his remarkable strength as well as his vulnerability, and to demonstrate that suffering (childhood adversities and career disappointments) often go hand in hand with unyielding striving leading to remarkable achievements.