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Contemporary interest in the neurosciences and cognitive studies has revitalized debates about the meanings and implications of free will and determinism. Dilemmas associated with the various positions remain relevant to a broad range of psychological theories and practices as well as to legal, moral, political, and religious beliefs and practices. Workable solutions to the issue remain as vexing and elusive as ever, partly because to date there is no concept of free will or determinism that does not do violence to some of the dimensions of ordinary human experience. For example, does a law-and-order, hard-wired, completely determined worldview foreclose on the possibility of any genuinely open future? On the other hand, are there self-generated autonomous activities entirely, or in any sense, free from material, formal, and social influences? This paper focuses on Freud's extensive but little-known struggles with the issue, particularly in the early years of his practice. Examining his work with fresh eyes uncovers intellectual minefields and meanings of freedom highly provocative, informative, and relevant to 21st century debates.