Careless Jewel (foaled March 4, 2006 in Kentucky) is a Canadian Thoroughbred racehorse.

Careless Jewel is out of the mare Sweet and Careless, and was sired by Tapit, a son of Pulpit by A.P. Indy by Seattle Slew. 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. She followed that with an 11-length victory in the Grade I Alabama Stakes over ten furlongs.^[4] She earned her fifth straight victory in the Cotillion Handicap in late September.

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. She did not race again.^[6]

Her first foal was by Street Cry (IRE) and in 2013, she became the first mare to check in foal to Bodemeister.^[7] She later had a colt by Tiznow (in 2015) and in 2017 foaled a filly by Pioneerof the Nile. Careless Jewel lives at Summer Wind Farm in Georgetown, Kentucky.