Richard "Dick" Stillings was born on March 7, 1944 in Mt. Vernon, Ohio. After graduation from high school he received his early exposure to harness racing by working as a groom for Hall of Fame Immortal Dick Buxton. Stillings' career in racing was interrupted by a three-year volunteer stint in the Army, including six months served in Vietnam as an air supply specialist. Upon returning to civilian life, Stillings found work in a local factory and quickly realized he preferred employment out-of-doors. He took jobs with Immortal Jimmy Cruise, Sr. and Hall of Famer Howard Beissinger,and moved from grooming to training.
In 1968 Stillings relocated to The Meadows in Pennsylvania, where he established himself as a top trainer-driver, just as the sport was moving towards trainers specializing in training and drivers in driving. In the 1970s, Stillings and his brother Charles ("Buddy") joined forces. At The Meadows, Stillings and owner Roy Davis formed a partnership that sent out a series of hard-battling Grand Circuit types, all of them with the surname "Spur" after Davis's favorite soccer team, Tottenham Hotspur of England.
In 1985, driven by Hall of Famer Bill O'Donnell, two-year-old Barberry Spur p,3,T1:50.2 ($1,634,017) was victorious in the $1.36 million inaugural Governor's Cup and a division of the Matron Stake, both at Garden State Park. Stillings drove Barberry Spur to a 1:55.2 world record for two-year-old pacers on a half-mile track in The Standardbred at Delaware, Ohio. Two-Year-Old Pacing Colt of the Year Barberry Spur was the leading moneywinner in his division with $971,147 in earnings, as well as the fastest on both a five-eighths and half-mile track.
In June 1986, Stillings drove Gunslinger Spur 3,1:58f ($317,562) to victory in the Yonkers Trot. Three-year old Barberry Spur's 1986 season included wins in the Adios (driven by Stillings), Cane Pace and Little Brown Jug (both driven by O'Donnell). Barberry Spur was the fastest Standardbred of 1986 (TT1:50.2), and retired holding the record for two-year-old pacers on a half-mile track (1:55.2) and the Standardbred record for a two-heat race on a five-eighths mile track (3:46.4), while ranking ninth among the leading moneywinning Standardbreds of all time.
Stillings piloted three-year-old Jaguar Spur p,4,T1:49.2 ($1,806,473) to victory in the 1987 Little Brown Jug, as well as in that season's Hanover-Hempt, Gaines Memorial and Tattersalls Pace. Later in his career, Jaguar Spur would record wins in the Driscoll Series, Mohawk Gold Cup, George Morton Levy, Graduate Series and Battle of Lake Erie (twice). The first pacer in history to record $500,000 seasons at three, four and five, Jaguar Spur retired as the twelfth-leading moneywinning pacer of all time. He also held the world records for four-year-old pacers on both a mile (TT1:49.2) and a half-mile (1:53h) track.
Stillings trained and drove 1988 American-National and Breeders Crown winner Kentucky Spur p,3,1:52 ($1,341,340), who retired owning the world record for two-year-old pacers on a five-eighths mile track (1:53.2f). In 1989, Colonial, Matron Stake and Breeders Crown-winning trotter Esquire Spur 3,1:56f ($336,250) was voted Three-Year-Old Trotting Colt of the Year, with Stillings receiving co-honors as Glen Garnsey Trainer of the Year. Stillings-trained Pegasus Spur 3,1:54 ($1,296,683) was runner-up in the 2001 Hambletonian Stake. As a driver, Stillings has earned over $40 million to date.
Dick Stillings continues to excel as both trainer and driver, to this day ranking high in the horsemen's colony at The Meadows. He and his wife Mary Lou live in Washington, Pennsylvania. He has one son, Rick, and two grandchildren, Sophia and Ella.