Bleakley was last seen in Clearwater, Florida on March 1, 2009. He was on a 21-foot fishing boat off the Gulf Coast with three other men: Corey Smith, Victor Marquis Cooper and Nick Schuyler. When they didn't return, the Coast Guard launched a search. They found Schuyler at 1:35 a.m. on March 2, clinging to the side of the overturned boat. He was suffering the effects of hypothermia and dehydration. The other three men were missing. Schuyler stated they had disappeared one after another. An extensive search turned up no sign of Bleakley, Cooper or Smith. They are presumed to be lost at sea.

Bleakley played football while attending the University of South Florida; he graduated in 2006. His body has never been found.