Jake Winslow has been a long time resident of southeastern Massachusetts. He spent his early years living in Somerset and Berkley. He graduated from Coyle Cassidy High School in Taunton in 1992. After high school, Jake attended Wesleyan University in Middletown, Connecticut, graduating with a degree in government in 1996. While at Wesleyan University, Jake played football and was president of his fraternity, Delta Kappa Epsilon. Jake’s first career revolved around football. He coached collegiately at Wilkes University in Wilkes-Barre, Pennsylvania and Trinity College in Hartford, Connecticut. He also worked for the Washington Redskins and Cleveland Browns front office staffs. Jake decided to change courses and attend law school in 1999. He graduated from Suffolk University Law School in Boston, Massachusetts in 2002. Since graduating, Jake has had a practice with a focus on all aspects of residential and commercial real estate. Jake currently lives in Rochester, Massachusetts with his wife and two children. He likes to spend as much of his free time as possible with his family at Bakers Beach in Westport, Massachusetts.