In 2016, the Kennedy Eagles football program lost a long time alum and coach with the passing of Winfield 'Win' Cheske.  Coach Cheske was a 1967 graduate of Kennedy High and played football on the 1966 NVL Championship team.  After graduation he joined the United States Marine Corps before returning home to begin a career in education.  He taught and coached in the Waterbury public school system for over 30 years.  He returned in 2009 to coach at his alma mater, JFK, until his passing in 2016.
The ‘Cheske’ Award is named in honor of coach Win Cheske.  Coach Cheske was a ‘gentle giant’ who taught more than the game of football.  He taught the game of life.  He demanded that all players respect their teammates and coaches.  He expected their best personal character on and off the field.  Coach taught our young men to work thru the challenges that they faced both on and in life.  The ‘Cheske’ is awarded to the player who best demonstrates a passion for the game of football that comes from one of Coach Cheske's favorite sayings, ‘Fire in the Belly’. 
The 'Cheske' honorees, 2016 to present...
2016-Jacob Colon and Jude Sampson
2017-Marc Soto and Cassius Arnold
2018-Nytoni Jones
2019-Chris Byrd
2021-Josh Bayarinas
2022-Miguel Castillo