Despite being widely read and the source of numerous oft-cited aphorisms “The Path of the Law” remains elusive. To put the matter starkly: What is its thesis? Does it have one? How can we reconcile its matter-of-factly opening pages and its almost mystical conclusion? For some this was just proof that Holmes was a superficial and contradictory thinker; for others it suggested that “Path” should be read a series of interesting insights and arresting phrases, and nothing more. In this essay I suggest reading Holmes’s famous speech as an essay with a thesis about, well, the path of the law. I argue that the essay should be divided into three parts, roughly corresponding to the law’s past, present, and future. This approach to jurisprudence was popular in the nineteenth century, but almost disappeared in course of the twentieth century. The rise of ahistorical analytic jurisprudence and the decline of grand narratives from historiography made Holmes’s main point easy to miss. But in both jurisprudence and history intellectual climates seem to be changing, making it easier for contemporary audiences to read and accept Holmes’s essay as part of the genre of evolutionary jurisprudence, to which it belongs.