Despite the importance of linguistic analysis, no systematic research has been explored in the form of linguistic analysis on personal statements for military orthopedic surgery residency programs. This study was conducted to analyze U.S. Navy (USN) orthopedic surgery applicants' personal statements using an automated textual analysis program to assess personal statements for linguistic styles. A retrospective analysis of USN orthopedic applicant personal statements from application years 2016 to 2019 was performed utilizing the Linguistic Inquiry and Word Count (LIWC) software. LIWC analyzed the text for summary variables: analytical thinking, clout, authenticity, and emotional tone. We compared this analysis with Step 1 and Step 2 scores and determined whether an applicant matched. A total of 94 personal statements (60,230 words) were analyzed using LIWC. The average word count was 640.7, with an average of 23 words per sentence. The average-matched applicant USMLE Step 1 and Step 2 scores were 240 and 250, respectively. When examining summary traits utilizing multiple logistic regression analysis, only analytical thinking demonstrated a statistically significant difference in matched versus unmatched applicants with a P = .011 (OR = 1.10). As the USMLE Step 1 exam transitions from a scoring system to Pass/Fail grading, programs will look at other characteristics to determine who would likely succeed in residency. From a linguistic analysis standpoint, matched applicants' personal statements demonstrated higher analytical thinking, clout, affiliation, power, and risk focus than unmatched applicants. Unmatched applicants demonstrated higher authenticity than matched applicants.