Massey was last seen in Huntsville, Alabama on November 30, 2000. Witnesses told authorities that Massey was inside a red 2001 Ford pickup truck with Alfred "Sonny" Hardy III prior to his disappearance. He has never been heard from again. The vehicle was discovered sometime afterwards in Cullman County, Alabama. The truck's owner was unable to provide any information regarding Massey's whereabouts. Witnesses may have also seen Massey earlier during the day in the company of two unidentified Caucasian males and one unidentified African-American male.

Hardy was arrested after Massey's disappearance and charged with the November 2000 murder of Derwin Tyrone Hawk. Authorities believe that Hardy killed Hawk inside a residence on Medaris Road in Huntsville. Massey may have witnessed the crime. Hardy was convicted of Hawk's homicide in 2001, although he maintains his innocence. He claimed that he was framed for Hawk's murder.

Authorities believe that Hardy may have killed Massey as a result of Hawk's homicide. No charges have been filed against anyone in connection with Massey's disappearance, which remains unsolved.

Massey may have traveled to the Birmingham, Alabama area. Some agencies may list December 1, 2000 as the date of his disappearance.