Hon. Robert Borden Cromwell Jr.

The Honorable Robert Borden Cromwell, Jr., 93, left this transitory life in the presence of God and his family on February 7, 2026. He was born on November 22, 1932, in Norfolk to Robert B. Cromwell, Sr. and Edna Gunther Cromwell. He was predeceased by his wife of 57 years, Barbara Heflin Cromwell, and his sister, Beverly Cromwell Wall.

Bob grew up on the Lafayette River and delivered newspapers for The Virginian-Pilot. He graduated from Granby High School in 1951 and immediately went to work for the Norfolk & Western Railway. At age 18, Bob was drafted into the U.S. Army and served two years in Korea. On his return, he used the G.I. Bill to attend the College of William & Mary. It was there that he met the love of his life and married Barbara in Williamsburg. For this reason, he would often say that getting drafted was the best thing to have ever happened to him. He graduated from the John Marshall School of Law at William & Mary in 1961and began practicing with Kellam & Kellam in Norfolk. In 1964, Bob and his close friend, the late Hon. Kenneth Whitehurst, Jr., opened a small law office at Robin's Corner in Virginia Beach. Bob served on the Virginia Beach City Council from 1966 to 1978, including four years as Vice Mayor (1966-1970) and two years as Mayor (1972-1974). He eventually helped form the law firm of Guy, Cromwell, Betz & Lustig in Virginia Beach. In 1990, the General Assembly appointed Bob to serve as a judge in Virginia's Second Judicial Circuit, which includes the Circuit Courts of Virginia Beach, Northampton County and Accomack County. During this time, he thoroughly enjoyed working with the staff, clerks, deputies, lawyers and fellow judges. He retired from the Circuit Court in 2002 and continued to serve as a substitute judge before retiring completely to care for Barbara, who passed away on May 19, 2017.

Bob was a true Virginia gentleman: kind, polite and humble to everyone he met. He loved his family fiercely and loved being a part of the extended Dickinson family. He is survived by his son James Thomas Cromwell, his son Richard Joshua Cromwell, his wife Payton Dickinson Cromwell, his two spectacular grandchildren, Luke Dickinson Cromwell and Holley Chase Cromwell, his nephew Charles Coleman Wall, III and his wife, Tara Duffy, his niece Elizabeth Alice Stuhlsatz and her husband David, and his grandnephew James Nicholas Wall. We will all miss him terribly.

The family acknowledges with heartfelt appreciation the care and attention provided to Bob by the staff and caregivers at Westminster Canterbury in Virginia Beach, especially Samuel Knight, and by the Intensive Care Unit nurses at Virginia Beach General Hospital.

A memorial service to celebrate Bob's life will be held on February 14, 2026, at 11:00 a.m. at Baylake United Methodist Church, 4300 Shore Drive, Virginia Beach, Virginia 23455.