Robert Sylvester Tripp Sr.

Robert S. Tripp Sr.

"He worked with his hands, led with his heart, and left a mark on his community that will never be forgotten. May the lines be tight and the gardens be green.

Born: September 10, 1940 - Died: February 8, 2026

Virginia Beach, VA - Robert S. Tripp Sr., a man of profound resilience, legendary skill, and a cornerstone of the Virginia Beach community, passed away on February 8, 2026, at the age of 85.

A Journey of Resilience and Talent

Born in 1940, Robert's early years were defined by the grit of the rural South. As a youth, he labored in the fields picking cotton, beans, peanuts, and watermelon-experiences that fueled a lifelong work ethic and a humorous, permanent distaste for picking fruits and vegetables. As a young boy, Robert truly hated picking. He detested the heat of the fields and the stigging of the insects.

By 1955, Robert was a standout student-athlete at Edenton High School. A powerhouse in both football and baseball, his talent on the diamond was so undeniable that he was recruited to play for the county's adult travel baseball team while still a teenager, competing at a level far beyond his years.

A Pillar of the Community

Robert moved from the fields of his youth to the entrepreneurial success of his adulthood. For 50 years, he owned and operated Tripp's Barber Shop. Behind the chair, he was more than a barber; he was a mentor, a storyteller, and a community anchor who saw generations of families grow up in his shop. He also dedicated many years of service to the Virginia Beach City Public Schools as a custodian, later a distinct administrator, where his meticulous nature and dedication ensured a better environment for the city's youth. Robert was a trustee at First Baptist Church East End and spent many years in a servant-leader capacity helping church members and feeding the homeless.

In his leisure, Robert found peace in the outdoors. He was an avid gardener who took great pride in a pristine yard and a thriving garden. However, his true joy was found in Hatteras, out on the Atlantic. An expert fisherman, he lived for the thrill of the strike and the challenge of catching King Mackerel in the deep blue.

Family and Legacy

Robert was first married to Mary Francis Tripp who was the mother of four of his children. Later he shared a long, and devoted marriage with Ola Mae Tripp, who was his partner and the mother of his youngest son. He was preceded in death by his mother, Katie Tripp; his uncle, John Lee Tripp; and his sister, Louise Perry.

His legacy lives on through his seven children:

Sherry Tripp Baulkman, Victor Andre Tripp, Robert Cooper, Charisse Renae Tripp, Sean Dean, Viveca Hayes, and Robert Sylvester Tripp Jr.

He is also cherished by his seventeen grandchildren:

Chanel, Nicolette, Tierra, Berica, Dajuan, Demond, Litisha, Naralton, Mary, Ikea, Brandon, Madison, Ethan, David, Lauren, Kayla, and Rob Jr; as well as a host of great-grandchildren, nieces, nephews, and friends.