Fentress left his Norfolk, Virginia home to attend a golf tournament in Richmond, Virginia on October 2, 2001. He took only his golf clubs and a small overnight bag. He checked into a Holiday Inn in Richmond at 6:00 p.m. Another guest at the hotel saw him at 10:00 p.m.; Fentress said he was tired and wanted to go to bed so he would be well rested for the next day's game. He never arrived at the golf course and has never been heard from again. When hotel workers checked his room, the bed did not appear to have been slept in and none of Fentress's belongings were located.

Fentress's four-door 1988 Oldsmobile was discovered locked and abandoned, stuck in the mud in a wooded area of Hanover County, Virginia on October 7, 2001. The site is 36 miles from Richmond. Fentress's golf clubs and overnight bags were in the trunk of the car, but the keys were missing. There was no sign of Fentress in or near his vehicle, and no indications of foul play. The area where the car was found is a popular spot for hunters and fishermen, but Fentress did not hunt or fish.

Since Fentress's disappearance, he has not used his credit cards or withdrawn cash from his bank account, where his pension checks are still automatically deposited every month. He formerly worked as a labor foreman with the Army Corps of Engineers; he retired in 1985. His family stated he was mentally sharp at the time of his disappearance. Authorities do not believe Fentress left of his own accord, but the circumstances surrounding his case are unclear.

Richmond authorities are handling Fentress's investigation.