Bred by Gainesway Thoroughbreds Ltd.[2] & Bill Andrade, the filly was sold at the September 2007 Keeneland Yearling Sale for $40,000.
She is owned by Verne Dubinsky of Alberta, Canada who races under the name Donver Stables, and is trained by Josie Carroll from a base at Woodbine Racetrack in Toronto.
[3] Careless Jewel came to prominence on the racing scene in July when she won the Delaware Oaks by over 8 lengths.
Ridden by regular jockey Robert Landry, Careless Jewell was the 9-5 favorite going into the November 6, 2009, Breeders' Cup Ladies' Classic world championship.
[5] However, the filly was uncontrollable and charged to an almost ten length lead, exhausting herself by the turn for home and fading to finish last.