Osgood was last seen boating on the Pacific Ocean between the California mainland and Catalina Island on April 30, 1988. He was on the Sea Lust, a 51-foot sailboat, and was on the rigging when he was knocked into the water by high winds at 4:00 p.m. Osgood was not wearing a life jacket at the time. The other people on the boat threw him a dinghy to hold onto and attempted to pull him back on board three times. By the fourth attempt, Osgood had vanished. An extensive search by the United States Coast Guard failed to produce any evidence as to his whereabouts.

Osgood was born in California but raised in Washington State. He was a resident of Canoga Park, California in 1988. He is a former professional jazz drummer and an Air Force veteran, and at the time of his disappearance he owned and operated a construction company out of his home. Osgood is described as an accomplished sailor; he owned two boats in 1988. He is presumed to have drowned at sea.