Jessie graduated from Christopher Columbus Catholic High School in 2006, where he was crowned the Iron Man champion for his senior class and also played football at the position of defensive end, eventually leading to several Division 1 scholarship offers. However, he opted to follow his lifelong dream and start his law enforcement career. At the age of 18, straight out of high school, Jessie was hired as a police trainee and entered the Broward Community College Police Academy , graduating at 19, taking the honor of “Top Shooter” and “Most Athletic” and later began his career working for the a local police department. In 2009, Jessie went on to graduate from one of the most prestigious and rigorous SWAT schools, making him the youngest officer to ever complete this course at that time, at the age of 21. Jessie served as a member of the full- time elite Crime Suppression Team (CST / SWAT) from 2009 to 2013; he later was promoted to Sergeant and continued serving the city in a patrol sergeant capacity and later returning to the SWAT team as one of the youngest ever team leaders.

One of the highlights of Jessie’s career was taking down a human trafficking ring, something that had never been done before in the city and subsequently has never been done since that time. While serving as a police officer and later a patrol sergeant, Jessie received numerous awards and commendations. His performance evaluations were excellent, and his record was stellar. He was a proactive sergeant and had the highest squad productivity statistics anywhere he was placed. Jessie served as a mentor to many law enforcement officers, sharing his knowledge, training and work ethic. He took advantage of training opportunities and enjoyed expanding his knowledge and training skills even on his own time and in most cases covering costs out of his own pocket.