Harry “Sammy” Samuel Winfrey III, also lovingly known as Big Sam, 76, of Newport News, VA, went home to be with the Lord on Monday, June 30, 2025.
Born January 15, 1949, to Harry Samuel Winfrey Jr. and Mary Kelley, Sammy lived a life full of laughter, love, and service to others. On February 16, 1974, he married Elva “Cissie” Stainback, and together they shared over 51 years of marriage, building a beautiful life and family. Their union brought together three children: Samuel, Shaun, and Summer, whom he loved beyond measure.
Sammy graduated from Ferguson High School in 1967 before being drafted into the U.S. Army in May of 1969. He proudly served his country in Vietnam, where he was awarded a Purple Heart with an oak leaf cluster for injuries sustained in battle. After being honorably discharged in 1971, he went on to work for the National Park Service starting in June 1978, a position he held with pride until his retirement in 2007.
Even after retirement, Sammy stayed active, working at Busch Gardens for 10 more years, where he brought his signature humor and warmth to everyone he met. He often made light of even the most difficult experiences, famously joking, “I was a damn war hero, I was in the big one,” with a grin and a wink. That kind of humor—sharp, unfiltered, and real—was part of who he was. He said what others were thinking, and you never left a conversation without a laugh.
To the many kids who knew him, he was simply “Dad.” He never missed a game, a practice, or a moment. He was the guy who took the whole carpool to the tournament, paid for every kid’s ticket, bought snacks for the team, and made sure no child missed out just because they couldn’t afford it. He worked extra jobs, made extra time, and gave extra love to anyone who needed it. His reach was wide, and his impact even wider—there are countless people who will tell you that they got to play ball or join a team because Big Sam made sure they could. If he loved you, he gave you a hard time—and you loved every minute of it.
Sammy was preceded in death by his parents, Harry Jr. and Mary, and by his sister, Sharon McEnerney, and her husband, Ronnie. He is survived by his wife, Cissie; his sister Sandra Wolpert and her partner Rich; his brother Steve Winfrey and wife Debbie; and his three beloved children: Samuel IV, Shaun, and Summer. He also leaves behind his nine granddaughters and one great-grandson: Amathyst Flippin and her husband Kyle, and their son W. Riggsley “Riggs” Flippin; Karagan and Talyn Winfrey, Scout and S. Belle “B” Winfrey; Taylor and Parker Chapman; and Josephine and Kaylee Munford.
To know Sammy was to be loved, teased, supported, and probably offered a snack from the concession stand he’d just bought out. His presence made life lighter, fuller, and funnier. He gave his all to his family, friends, community, and country, and he will be deeply missed by all who were lucky enough to know him.
Hug your kids, take them to the game, and don’t forget to laugh—Big Sam would insist on it. A visitation with closed casket will be held on Monday, July 21, from 5:30 to 7:30 p.m. at Peninsula Funeral Home, 11144 Warwick Blvd, Newport News, VA 23601. Graveside services will follow on Tuesday, July 22, at 11:00 a.m. at Albert G. Horton Jr. Memorial Veterans Cemetery, 5310 Milners Rd, Suffolk, VA 23434.
4 Comments
My boyfriend (Josh) and I were going to attend the viewing today. But, our child got really sick this morning and she’s still ill. I know that Mr. Sam would rather us take care of our child instead. We both worked alongside Mr. Sam at Busch Gardens, he was the sweetest (to us at least) of course he would let you know if he liked you or not! Haha! Very funny man and I always enjoyed seeing his face on the days him and I worked together! Sending so many healing blessings to your family. If there is any other way besides our comment; to pay our respects more please let us know!
I’m sorry to hear about Sammy. His laugh would make one smile.
I worked with Sam at Busch Gardens for ten years. We became best friends. We would do a lot of trash talking to each other. We had so fun together and still managed to our work done. Those were the best times I had. I’m going to miss him. I always treasure the fun times we had working together. I will never forget him.
I worked with Sam at Busch Gardens for ten years. We had so much fun working together. We did a lot of trash talking, but still managed to get our work done. I really looked forward in working with Sam. We became best friends. I will never forget him. Sam would pick me up, so we would ride together at work. I would enjoy having lunch with him outside of work. Sam was the best.