Crockett was last seen in the Chesapeake Bay on March 10, 2005. He left his Tangier Island, Virginia home and took his 38-foot fishing vessel, the Eldora C and took his pet cat to a vetrinarian appointment in Crisfield, Maryland, thirteen miles away. Crockett left the vetrinarian's office at noon to sail home.

There was a severe storm that day, with snow, 58-mile-per-hour winds and six-foot swells. While out on the ocean, Crockett radioed a man on a nearby boat, but didn't indicate there was anything wrong. The other sailor pulled ahead of Crockett and lost sight of him. He was scheduled to return to the island by 1:30 p.m., but he never arrived. The Coast Guard began searching for Crockett at 3:30 p.m. The only thing they found was a life ring from the Eldora C and a small oil slick, south of Watts Island, Virginia.

Crockett is a very experienced fisherman who lived on Tangier Island his entire life. He has four sons, all of whom are also fishermen. One of Crockett's sons died of cancer in 2005, and Crockett's wife died in 1982. He is presumed to be lost at sea, but his body and his boat were never recovered.