Osborn disappeared with his friend and coworker, Rickey Kutej. They worked at a garage owned by Osborn, near 5th Street and U.S. Highway 270 in Alderson, Oklahoma. They were last seen on the morning of March 26, 2003 in McAlester, Oklahoma. The two men planned to go to the garage to complete some odd jobs. Later that day, the police were summoned to the garage because it was empty. They found the garage open, but deserted. Someone had been working with a bulldozer and there was an overturned ladder and a small amount of blood on the ground. Authorities theorized one of the men fell off the ladder and hurt himself, but there is no record of either Osborn or Kutej seeking medical attention. Neither of them have ever been heard from again.

Osborn and Kutej may be traveling with a black 1999 Dodge Ram 3500 pickup truck with Oklahoma license plates and custom aluminum parts. The circumstances of their disappearances are unclear.