Racing Career
Flannery began racing on a snowmobile before switching to a two wheel drive Class 6 off-road racing utility vehicle in the early 1970s. He started racing a buggy in 1974 before he moved up into full-size trucks in the late 1970s. He left the Midwest and competed in the selected Western United States desert events when he raced in the 1978 and 1979 Mint 400. In the early 1980s, he twice raced in the Canadian Off-Road Series while winning five class titles in SODA. Flannery competed in SCORE International in the Western United States during that time period.
In 1990, he won the SCORE race at Phoenix, Arizona. That same year, he won the Class F division in his Ford and was awarded the Rookie of the Year award at the Pikes Peak International Hill Climb. Flannery changed to a Chevrolet in 1991 with his "Chevy Thunder" team that he would become most known for. That year he won nine of ten events in SODA's ESPN TV-Pro series. He also won the Heavy Metal division at Pikes Peak and broke his own record by climbing the hill 22 seconds faster. In 1992 he competed at Pikes Peak, setting the record for the fastest hill climb in the Unlimited Off-Road Truck class. In 1996 he won the $125,000 Borg-Warner World championship off-road race race at Crandon en route to his sixth ESPN Pro Series championship. Flannery won the major 1997 events at Crandon, winning the Governor's Cup in Spring and both his class and the Heavy Metal Borg-Warner World Championship races in fall en route to winning the 1997 SODA Class 4 championship.
Most of the drivers in SODA changed to new short course off-road racing series CORR after the 1997 season. Flannery narrowly won the 1998 CORR Pro-4 (4WD) championship over his son Jamey. Flannery won another Governor's Cup race in 1999.
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