This work sought to comprehend the tax implications for those former players of the National Football League (NFL) who are making personal injury claims against the league for expenses they endured since they retired. To achieve this objective, Section I of this paper contextualizes the concussion debate by highlighting studies of head trauma on NFL players to show the settlement of personal injury claims may not be enough with respect to the impending complex federal income tax issues some players will experience. Sections II and III interprets the Internal Revenue Code and the specific sections applicable to the former NFL players for injured parties contemplating reimbursement for past or future related medical expenses. Lastly, Section IV presents recommendations to each party (i.e., retired players and the NFL) on how to possibly revise the settlement to achieve better tax consequences.