Charley Bennett is one of Portland High School’s greatest all-time athletes. His exceptional accomplishments earned him state-wide recognition and honors not only in baseball, but also in football, basketball and tennis. Legendary P.H.S. coach Jimmy Sibson emphasizes his “outstanding character, versatility and leadership qualities”.
At Portland High School, Charley was the spark-plug of Bulldog baseball for three seasons as the team’s shortstop.
During his years at P.H.S., the Bulldogs captured one Telegram League title and were runners-up in another season.
His baseball prowess earned him an invitation during his junior year to Fenway Park for a Red Sox tryout.
After accepting an all sports athletic scholarship to Boston College, Charley started at halfback for the B.C. Eagles as a freshmen in the fall of 1945.
However, his college career was interrupted by a three year stint in the United States Navy, where he did play three years of high level service baseball.
Upon his return to college, Charley transferred to Bowdoin College. He originally played football (All State), basketball and baseball, but academics and injuries eventually curtailed his Polar Bear baseball career. During the late 1940’s and early 1950’s, Charley also played semi-pro baseball in the Portland Twilight League.
He played on two championship teams, the Emerald A.C. and the Haskell Aces, along with several other MBHoF members - Andy Lano, Carlo Tucci, Sonny Noel, Willie Greenlaw, Frank Nappi, etc.
in 1955, Charley began a 37 year career in education, from Biddeford High School to Portland’s Jack Junior High to the Kennebunk Middle School.
he coached at all three schools, including football, basketball, tennis, swimming and baseball (18 years). Charley officiated a combined total of sixty seasons of football, soccer, basketball and baseball.
in addition, for thirty years he ran recreation programs in Portland and Kennebunk.
Charley and Marie, his wife of 45 years, now reside in Kennebunk.
They raised nine children - Charles Ill, Jonathan, Stephen, Peter, Michael, Paul, Mary, Victoria and Sara - and currently have eight grandchildren.