We employ the concept of word sense disambiguation to determine the inherent meaning of voter intentions regarding possible political candidates from the 2016 Presidential election. We present our findings based on a website (www.presidentselect.com) that we developed, where candidates can be examined and their true assets and competencies in three major areas of eligibility, education, and experience inputs can be deciphered. Data envelope analysis is used to determine underlying word instances for elected and successful outputs. We also utilize our web site results to longitudinally extend these findings for decision making of potential election fraud detection in the 2020 Presidential election, utilizing Benford’s Law. Our results shed light on these phenomenon and provide new insights into the word sense disambiguation literature.