5 Longest Prison Sentences in U.S. History Charles Scott Robinson: 30,000 years. ... Allan Wayne McLaurin: 21,250 years. ... Dudley Wayne Kyzer: 10,000 years. ... James Eagan Holmes: 12 life sentences and 3,318 years without parole. ... Bobbie Joe Long: 28 life sentences, 99 years, and 1 death sentence. Aug 28, 2015