In 2007, Gaines' trainee
Nashoba’s Key would go to win over $1m in winnings in just ten races before being euthanized after an accident. Nashoba's Key was named the 2009
California Horse of the Year and later inducted into the California Thoroughbred Breeders’ Association Hall of Fame in 2023. In 2009, Gaines had the biggest win of her career when
Dancing in Silks won the Sentient Jet
Breeders' Cup Sprint at
Santa Anita Park. Dancing in Silks owner advocated to enter the horse in the race against Gaines' advice. A longshot at the start of the race, Dancing in Silks won a purse of $1,080,000 for his victory in the race. Dancing in Silks was later named the 2009
California Horse of the Year, sharing the honor with
California Flag. In 2010 and 2011, Gaines campaigned
Malibu Pier to multiple stakes wins and a place in the La Brea Handicap. In 2015, Gaines brought Bolo to the
Kentucky Derby, making history as the sixteenth female trainer to campaign a horse in the race. Bolo would end up finishing twelfth in the Derby. Four years later in 2019, Bolo won the $500,000
Shoemaker Mile Stakes at Santa Anita Park. In 2024, her trainee mare Closing Remarks was named the 2023 Champion California-bred Turf Horse and Champion California-bred Older Female by the
California Thoroughbred Breeders Association. Closing Remarks was retired from racing in March 2024. In 2024, Gaines's trainee Hot Girl Walk won the $100,000 Generous Portion Stakes in
Del Mar, California. == Controversies ==