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Directly or indirectly, Jim Bowie’s enigmatic illness during the siege of the Alamo resulted from his own actions. A hearty man of six feet in height, Bowie was a walking contradiction; a slave trader who fought for freedom, a generous and congenial man who called out his thunderous temper on a whim, and a commanding leader who was prone to binges of sloppy drunkenness. He was determined in his actions and proceeded through life with an indestructible will, yet found himself bed-ridden as he took his last breath. Many suppositions have been made as to the cause of his infirm, including typhoid fever, pulmonary consumption, and traumatic injury. Other possibilities will be proposed in this text and will all lead to the conclusion that by indirect association or direct action, Jim Bowie contributed to his own demise.