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Remembering Win Headley

Win Headley — one of the most storied athletes in Staples High School history — died last Wednesday in Naples, Florida. He was 73 years old. His family says:

Born on the Fourth of July 1949, Winthrop (Win) Sargent Headley was a real-life Yankee Doodle Dandy.

He became an All-American football player, a lifelong football coach, a successful Wall Streeter, a loving family man, a passionate volunteer, an avid golfer, a loyal friend and a man of faith.

Win was born in California and raised in Westport. He starred as a Staples football player, and state champion heavyweight wrestler.

Win attended Wake Forest University, where he was a football All-American, captain and MVP on its ACC championship team. He received WFU’s first annual prestigious Arnold Palmer and Brian Piccolo Awards as an outstanding athlete, and is in the university’s Hall of Fame.

Win Headley at Wake Forest University.

He was drafted by the Green Bay Packers, and played for the Montreal Alouettes in the Canadian Football League. His career was shortened by injury.

He found a true calling as a coach. Over the years, Win coached at 3 universities (Winston-Salem State, Wake Forest and Princeton) and several high schools.

While in Princeton, New Jersey Win married Patty Cashill. They raised a family, and he had a long, successful career as a financial advisor for institutional investments.

In retirement in Naples Win continued to coach. He also volunteered in libraries, animal shelters and with the Knights of Columbus.

As Arnold Palmer would say, Win “played on through” when he peacefully passed away in his sleep on January 18.

Win Headley

Win is survived by his wife Patty; children Summer and Jonathan; sister Lynn Kelly (Michael); 2 nieces, 1 nephew; stepdaughter-in-law Rachel Y. Watlington, and step-grandson Christopher T. Watlington. He was predeceased by his stepson, Thomas Watlington III.

As Win would say, “The long and short of it”: Winthrop Sargent Headley was a man of passion and faith. He was a loving father and husband, and a devoted friend.

There will be a celebration of his life at a later date.

In lieu of flowers, Win would have appreciated your support for the Deacon Club (499 Deacon Boulevard, Winston-Salem, NC 27105) and the Humane Society of Naples (370 Airport-Pulling Road, North Naples, FL 34104).

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