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O’Leary came to the Sturgis Rally to race for the first time in 1948. In 1949 he won the amateur final and in 1950 he broke the track record of 29.75 seconds, posting a time of 29.06. Dick was looking forward to more wins that week, however due to heavy rains, the races were moved and wet track conditions caused him to go down in the third turn, breaking all of the bones in his left foot.

After a short time (he took his cast off after four weeks), Dick took off for the East Coast where he had several wins as an amateur. Heading south for the winter O’Leary tried his hand at “Outlaw” races, races that were not AMA sanctioned, and learned a lesson in competing in “wildcat” racing. After winning the “Tri-State Championship”, he and other riders discovered that the race promoters had taken off with all the gate receipts.
In 1951 Dick returned to Sturgis almost taking the Sunday final where he was beaten by his friend Bill Tuman “by a wheel”. 1952 was a great year for O’Leary, taking second place at the Michigan State Championship and winning several other races culminating with his win at Dodge City, Kansas.
In the spring of 1953 in a race at Mishawaka, IN, O’Leary was involved in a serious accident when another racer went down and slid into his bike. The other rider hit the fence but O’Leary cleared it and landed hard breaking his back and mangling his leg, which he almost lost to amputation. This accident effectively terminated Dick’s career as a racer.
Dick O’Leary was inducted into the White Pine Flat Trackers Association as a charter member in 1982 and went on to serve on the Board of Directors. He treasures his years as a motorcycle racer and returns to Sturgis whenever he can.