It was another gathering of some 108 graduates of Leonardo High School recently when the annual class reunion of the former high school in Middletown held its 93rd reunion, which was held, as in all recent years, at the Shore Casino.
Graduates came from as far as Massachusetts, Georgia and Colorado for the annual event, many with spouses or siblings accompanying them. They came from all walks of life, including three graduates who attend regularly, and all are retired from the Middletown Police Department. Former Chief Robert Letts, Former Detectives George Freibott and Irwin Beaver sat with their respective classes renewing friendships and stories they have shared over decades.
Freibott’s sister Ruth McDonald, another Leonardo High graduate attended with her brother. She was a long-time employee at the Courier, the local weekly newspaper .
Highly organized Richard Winters of Sunnyside Road, Lincroft, headed the committee who arranged and coordinated efforts for the annual event. Winters, who has lived in his Lincroft home for 74 years, said he looks forward to the reunion annually because “it’s just fun, it’s great to see old friends.”
Winters is a retired civil engineer who worked in highway construction for 46 years and has worked on “just about every local, county and state road in New Jersey,” including both the Garden State Parkway and the New Jersey Turnpike, as well as both the approach to the Verrazano Bridge and routes 287 and 195.
Winters said he learned all his expertise and continued to be promoted within the company on the job from the time he started as a bulldozer operatior until he retired as executive vice-president of Hess Brothers the firm where he worked all those years. He had also attended Monmouth Junior College before deciding on his career in road construction.
At 93 years of age, Winters has been chairman of the Leonardo reunion for the past 18 years and this year introduced Bill Brown, “to let the younger guys get more involved.” Working with Brown for next year’s reunion is Mike O’Brien. The reunion will be held at the Shore Casino on September 26, 2025.
Leonardo High School closed in 1958 when the building went on fire. Middletown High School on Tindall Road, now Middletown High School North, was under construction at the time and open in 1959.
“Only seven more years to go,” Winters chuckled, saying he is looking forward to the 100th class reunion of Leonardo High School.
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