After a lifetime of dieting, Oprah met the personal trainer in 1992, when she was at her all-time heaviest – 237 lbs. Since then, Greene has been there for her weight-loss triumphs (showing off her toned, 160-lb. body on the cover of O in 2005) and her setbacks (gaining 40 lbs. four years later). His reward: The media tycoon threw Greene a lavish, black-tie wedding at her Montecito, Calif., estate when he married in 2004.