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).

10 responses to “Remembering Win Headley

  1. Win Headley was a sports legend back in the day—someone younger aspiring athletes looked up to and wanted to emulate. He was in my brother’s class and was very welcoming to my brother when my family moved here in the spring of ‘63. (I’m pretty sure Win and Marc basketball together at Long Lots.)

    And I did see him wrestle at Staples. He was dominant.

    I can imagine he was a beloved coach. That seemed like a perfect calling for him.

  2. Kathy Herstein Weiss

    Win was a friend and classmate you never forget. We were in the same homeroom all through Staples, and graduated together in 1967. He was a star athlete in every sense of the word, but never let it “go to his head,” as he was very kind, caring and considerate to all. If I remember correctly, he was also crowned Homecoming King along with Kim H. in 1967. So sorry to hear of his passing.

  3. I was so saddened to learn of Win’s death. It was truly an honor to have played on the same Wreckers team with Win back in the mid-sixties at Staples. He inspired others by his commanding athleticism and, more importantly, by the manner in which he lived his life- one marked by caring, kindness and genuine humility. RIP Win, respectfully Steve Emmett

  4. Bonnie Scott Connolly

    I am very sorry to hear about Win. I was also in the class of 1967. Win was a very kind person. I was definitely not in the “In” crowd and he always spoke to me and was just very nice. It really makes an impact on people.
    Also, for one or two years his family hosted and housed Carolyn Hacker, a young woman our age who came to the area to train in gymnastics under former Olympian Muriel Grossfeld (in New Haven, I believe.)
    Carolyn was headed to the Olympics but I believe in the end was sidelined by an injury. But she was in our class also and it was fun knowing her and seeing her in an exhibition with Muriel Grossfeld. I’m not sure what the connection was between Win’s family and Carolyn Hacker but it was fun to know a possible Olympian.

  5. Chip Stephens SHS 73

    Although Win was 7 years before my time at Staples his name was always around from the Football stories from Coach Paul Lane and Saul “Neb” Pollak to the weight room rats we all know his name and were lucky to meet him now and then on visits to the gym. True legend as beast of the weights and on the field. Sorry to see his departure but legend will always live on.

  6. Stephen K Doig (Staples '66)

    Win was a wonderful Wreckers teammate. I’m glad for him and his loved ones that he had such a successful and fulfilling life after Staples.

  7. Terry Brannigan

    One of the greats from an era of gentleman multi-sport athletes (and leading man looks)

  8. Like the Steves–Doig and Emmett–I was a teammate of Win’s 1964-65. He was a fierce and dominating athlete in football and wrestling. He was also a fine golfer on the Wrecker golf team and would have been an outstanding pitcher on the baseball team. Yes, Win was a gentleman and a very kind guy. Off the field, he was very, very funny. In 1965-66 I was president of the Community Service Club, what passed for an athlete’s (mainly football) fraternity back in the day. Win always took our name and charter seriously, never missed a meeting at the Y and was generally hilarious at meetings. Good-bye big guy. Your former teammates honor you and will miss you. Tom Allen ’66.

  9. Dear Headley Family,
    I am so saddened to hear of the passing of Win. As a Westport schoolmate of Win’s I know he spent many hours in the gym lifting weights and doing other exercises to improve his on-field performance. Win was not only a good athlete naturally, but he was a great athlete because he worked as hard as anyone could to make himself better. Anyone who knew Win knew the work ethic and effort he brought to his game. Win never took anything for granted – he always went the extra mile to improve his performance. Win was a great teammate and a greater competitor. He was always fun to be around and I know he will be missed. Yet we can all keep our chins up knowing Win is now in a better place enjoying his just rewards. Enjoy, my friend.

  10. A life ended too soon – I had no idea Win was living here in Naples. Haven’t seen anything in the Naples Daily News. I’m from the Class of ’66. He was definitely the big man on campus. I am so sorry for your loss Headley Family.

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