Study Design: This is a retrospective case series using the Thomson Reuters Westlaw Edge database, an online subscription-based database of over 40,000 state and federal records. Objective: There is growing academic interest in the medical malpractice literature. The primary objective of this study was to examine medical malpractice in orthognathic procedures in order to characterize factors that determine legal responsibility and help make the craniomaxillofacial (CMF) surgeon more comfortable when treating this patient population. Methods: The database was queried for medical malpractice cases involving orthognathic surgery from 1985-2021. The characteristics of each lawsuit were identified, and descriptive statistics were reported. Results: A total of 42 CMF malpractice cases were available for review, and total of 15 cases were included in the final sample. Verdict decisions and settlements occurred between 1991 and 2012. Of the 15 cases, the highest concentration of cases occurred in California (6) and Pennsylvania (2). 53% of cases were ruled in favor of the defendant, 7% of cases were settled, 27% of cases were ruled in favor of the plaintiff against the surgeon, and 13% were ruled in favor of the plaintiff against the hospital with the surgeon being found not liable. The minimum award of damages was $29,999 and the maximum was $550,000. Conclusion: Litigation experience can be very time consuming and troublesome for medical practitioners. The risk of litigation and complications might be a prohibiting factor as to why CMF surgeons may not be preforming orthognathic surgery. The best defense against a malpractice case is to avoid one altogether. Learning from past mistakes is one way of ensuring that goal.