Bobby left Miami, Florida in 1959 in search of “racing territory”. He had with him his brother Donnie who rode along mainly for the adventure of the whole trip. Also along on the trip were two other Florida youngsters, Kenny Andrews and Gil Hearn. Gil went along to drive for Kenny. As they drove into Montgomery, Alabama they spotted a very attractive 34 Chevy modified with a Cadillac engine parked at a gas station. There they met the owner a young man named Bo Freeman. Bo showed them Montgomery Speedway. There they found out that races were being run that very night at Dixie Speedway in Midfield, Alabama.
It was a Friday Night and away they went. Bobby finished 5th in the heat, 5th in the semi-final, and 5th in the feature. That one night paid more than any one of them had ever won in South Florida even finishing as high as second in a special event. The next night (Sat.) Montgomery Speedway was running so they headed there. Bobby had fast time, won the heat and the semi-final, won the Australian Pursuit race and finished second to Sonny Black in the feature. They then went over to Georgia for the peach bowl in Atlanta on Sunday Night.