Cover photo for Leo Richard Orenstein's Obituary
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Leo Richard Orenstein

August 1, 1943 — July 27, 2023

Leo Richard Orenstein

   Lieutenant Colonel Leo Richard Orenstein, US Army Retired, 79, of Hertford, NC, died Thursday, July 27, 2023 in his home after losing his fight with cancer.

   Richard was born in Southport, NC on August 1, 1943. He moved often to follow his father’s Navy and Coast Guard assignments, but periodically returned to Southport for schooling and graduated at age 16 from Southport High School as Salutatorian in May 1960.

   Leo enlisted in the U.S. Army in January 1961 and served one tour in Laos and two tours in Vietnam. Ten of his 29 plus year career in the Army was spent overseas. Leo served in command and staff positions in Special Forces, Training Command, Mechanized Infantry, Fixed and Rotary Wing Aviation, Defense Nuclear Agency, Headquarters Dept. of the Army, Defense Intelligence Agency, and U.S. Embassy Jakarta as Attaché. Following retirement from the military, he founded and ran an international trading and consulting company in Manassas, VA for 17 years.

   He was preceded in death by his wife of 47 years, Deanna Sink Orenstein, his mother, Gilda Arnold Rogers of Southport, and his grandparents, Clifton and “Miss Annie” Arnold, also of Southport.

   Surviving is his wife, Beth Clayton Sessoms; his sister, Gina Rogers Jones (John); brother, Heywood “Woody” Orenstein (Lorraine); daughter, Scarlett Orenstein Grose (Matthew); grandson Carter Grose, and granddaughter, Sydney Grose. Also surviving are Beth’s children, Douglas Miller (Katie), Andrew Miller (Lauren) and Dr. Emily Ray (William); and six granddaughters, Katelyn Miller, Elizabeth Miller, Caroline Miller, Emily Miller, Annie Laurie Ray, and Margaret Ray.

   A gathering and time of visitation will be held Saturday, July 29, from 2:00 to 3:30 p.m. in Miller & Van Essendelft Funeral Home, 1125 Harvey Point Road, Hertford.

   A graveside service with full military honors will be held at a later date in Arlington National Cemetery followed by a celebration of his life.

   In lieu of flowers, contributions in his memory may be made to Gary Sinise Foundation, or to the United States War Dogs Association,

   Online condolences may be made by visiting

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Past Services

Gathering for Family and Friends

Saturday, July 29, 2023

2:00 - 3:30 pm (Eastern time)

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