He had great success with Cochise, winning several important races between 1949 and 1951, including the Massachusetts and Arlington Handicaps and the Saratoga Cup and set or equaled track records at Suffolk Downs and Delaware Park.
In July 1950, with the colt Greek Song, Raines won the Arlington Classic, a race that at the time was one of the most important in America.
Their union produced Greek Money who would give Buddy Raines his most important win in 1962 when the chestnut colt won a U.S.
On a personal basis, Buddy Raines played a major role in the rearing of his grandsons John and Mike Luzzi who both became jockeys.
One of the family's great memories came in 1991 when the eighty-year-old Raines saddled Timely Warning and watched as grandson Mike Luzzi won the Maryland Million Classic and the Brooklyn Handicap.