Background: The prosperous financial relationship between physicians and industry remains a highly scrutinized topic. Recently, a publicly available website was developed in conjunction with the U.S. Affordable Care Act to shed light on payments from industry to physicians with the goal of increasing transparency. The purpose of this study was to assess possible relationships between industry payments and orthopaedic surgeon gender, subspecialty training, and practice settings. Methods: A retrospective analysis was performed using publicly available information from the Centers for Medicare & Medicaid Services (CMS) to identify the 25 orthopaedic surgeons with the highest compensation from each of the 10 largest orthopaedic companies from 2013 to 2017. Statistical analyses were conducted to investigate the factors that contributed to payment differences. Results: Among the 347 highest-compensated orthopaedic surgeons, only 1 woman (0.29%) was identified. Orthopaedic surgeons in the subspecialties of spine (32.9%), adult reconstruction (27.9%), and sports medicine (14.5%) made up a majority of the 25 highest earners. A larger proportion of the physicians in this study worked in private practice (57.6%) compared with an academic setting (42.4%). Orthopaedic surgeons who subspecialize in sports medicine had significantly higher total mean payment amounts when compared with all other specialties. The primary method of compensation was found to be through licensing or royalty payments. Conclusions: The large majority of orthopaedic surgeons who are highly compensated from industry are men. Among these, the greatest number specialize in the spine, while sports medicine surgeons receive significantly higher total mean payment amounts. Additional studies are warranted to evaluate the disparities between men and women and encourage policies to promote gender equality.