Early Career
Bickle was brought into the sport as a child, when he watched his father, Rich Sr., race throughout Wisconsin. The younger Bickle began racing motocross at the age of five. While winning the 250cc championship on Sunday nights when he was 16, he raced stock cars at Jefferson Speedway on Saturday nights in 1977. He went behind his father's barn to pick out one of his father's old racecars and selected a beat up 1968 Pontiac GTO. "It was so beat up you could hardly tell what it was." Bickle started racing a 1974 Pontiac as a sportsman at Jefferson for the second half of the 1977 season and the whole 1978 season. Bickle stopped racing motorcycles after he graduated in 1979. He built a 1972 Ford Torino with a 302 cubic inch motor that year, which he began using at mid-season. He used the car to win a heat and the semi-feature at Columbus 151 Speedway in the car's first night out, and it ran well at Lake Geneva Raceway and Rockford Speedway. That off-season he changed the rear clip on the car to improve it for Rockford before deciding to give away the car and build a new one. In 1980 he raced weekly at Rockford, Lake Geneva, and Capital Speedway (now Madison International Speedway), winning 23 semi-features which was the most in the United States. He was named the Sportsman Rookie of the Year at Lake Geneva and Rockford.
Bickle turned his Rockford car into a late model in 1981 and raced the car to a Top 5 points finish at Lake Geneva and ninth place at Capital. He raced the car at Slinger Super Speedway and selected ARTGO races. He won his first late model feature that season at Lake Geneva. For 1982, he decided to try to ran as many races as he could within 300 miles of his home, and he had raced in between 90 and 100 events by the end of the season. He had won a couple of features and had set fast time at Wisconsin Dells Speedway (now Dells Raceway Park). At the off-season banquet for Slinger Super Speedway, he told track owner Wayne Erickson that he would win the 1983 track championship. Bickle focused on winning Slinger's track championship that year and he finished in the Top 5 in 17 of 18 features that season to win the track championship. In 1984 he raced primarily at Slinger, Wisconsin International Raceway (WIR), and Capital. Bickle won his first half mile feature at WIR even though he had raced at Capital for several seasons.
Bickle updated his car, hauler, engine, and equipment for 1985 with a new sponsor. He won the season opener at Capital and several other features later in the season en route to winning the track championship. He had a good season at WIR and raced well at the ARTGO races that he ran. In 1986 he won the points championship at Capital Speedway. He had 17 feature wins that season, and he ran well at Slinger, WIR, and Wisconsin Dells. In 1987, he raced at numerous Wisconsin tracks. He won a $15,000-to-win event at Calgary, Alberta, Canada in 1987. Butch Miller, who had led most of the race, went in for a pit stop with 60 laps left and Bickle and Ted Musgrave gained the lead. The race was halted for rain and hail with 46 laps left, and it was declared over with Bickle receiving the win.
He had won 230 races at various short tracks, including Lake Geneva Raceway, Wisconsin International Raceway, and late model track championships at Slinger Super Speedway in 1983 and 1989. Bickle won the Snowball Derby at Five Flags Speedway a record five times: 1990, 1991, 1996, 1998 and 1999.
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