Taxes played a surprisingly prominent role in the life of Ernest Hemingway—so much so that he personally dealt with, or wrote about, most of the major tax concepts embodied in the Internal Revenue Code. This article notes Hemingway's written observations about such tax matters, including remarks about the state of his tax affairs and possible investigations by the Internal Revenue Service. The article, which focuses on tax issues not typically covered in existing biographies, concludes with an assessment of Hemingway's outlook on and approach to dealing with extraordinarily onerous tax obligations.