Dreaming of Anna (USA)
February 5, 2004 – January 9, 2018
Rahy (USA) x Justenuffheart (USA), by Broad Brush (USA)
Family 2-d
February 5, 2004 – January 9, 2018
Rahy (USA) x Justenuffheart (USA), by Broad Brush (USA)
Family 2-d
After setting a course record at Colonial Downs and defeating colts handily over turf in the 2006 Summer Stakes (CAN-G3), Dreaming of Anna was pointed to the Breeders’ Cup Juvenile Fillies (USA-G1) on dirt because there was no equivalent race on the grass. (The Breeders’ Cup Juvenile Fillies Turf was not inaugurated until 2008.) She earned an Eclipse Award with a performance that saw her kick away from a challenge by 2006 Adirondack Breeders’ Cup Stakes (USA-G2) winner Octave, who would win two Grade 1 races the following year. Dreaming of Anna continued to race well at 3 and 4 without earning another top-level score. She did fairly well in a regrettably short broodmare career.
Race record
17 starts, 10 wins, 3 seconds, 1 third, US$2,024,550
2006:
2007:
2008:
Honors
Eclipse Award, American champion 2-year-old filly (2006)
Assessments
Highweighted at 123 pounds on the Experimental Free Handicap for American juvenile fillies of 2006, 3 pounds above second-rated Octave.
Topped Canadian-raced juvenile fillies of 2006 on the Canadian Thoroughbred Ratings with 107 pounds.
As an individual
An attractive, refined chestnut mare, Dreaming of Anna had plenty of natural speed and preferred to run on the lead. A good mover, she was game and determined in a drive.
As a producer
Dreaming of Anna produced six named foals of racing age; all six ran and five were winners. Her important foals are as follow:
Connections
Foaled in Kentucky, Dreaming of Anna was bred and owned by Frank C. Calabrese. She was trained by Wayne M. Catalano and was ridden to her win in the Breeders’ Cup Juvenile Fillies by Rene Douglas. Dreaming of Anna remained in Calabrese’s ownership throughout her broodmare career. She died of a ruptured aorta on January 9, 2018, at Woodspring Farm, Kentucky.
Pedigree notes
Dreaming of Anna is inbred 4x5 to 1960 American champion juvenile male and 1970 American champion sire Hail to Reason. She is also inbred 5x5x5 to Hail to Reason’s sire, 1953 Garden State Stakes and 1954 Flamingo Stakes winner Turn-to. She is a full sister to multiple Grade 2 winner Lewis Michael and a half sister to multiple Grade 2 winner Justenuffhumor (by Distorted Humor). Dreaming of Anna is also a half sister to Desert Song (by Unbridled’s Song), dam of German listed stakes winner Spanish Honey (by Iffraaj), and to Justenufftime (by Giant’s Causeway), dam of 2014 Monmouth Oaks (USA-G3) winner Cassatt (by Tapit).
Dreaming of Anna and her siblings are out of multiple listed stakes winner Justenuffheart, a half sister to 2004 American champion turf male and two-time American champion sire Kitten’s Joy (by El Prado). Justenuffheart is also a half sister to multiple Grade 1 winner Precious Kitten (by Catienus), dam of 2015 Coolmore Lexington Stakes (USA-G3) winner Divining Rod (by Tapit) and 2020 Endeavour Stakes (USA-G3) winner Jehozacat (by Tapit). In addition, Justenuffheart is a half sister to Striking Image (by Red Ransom), dam of stakes winner Self Made Man (by Catienus). Finally, Justenuffheart is a half sister to Last Kitten (by Catienus), dam of listed stakes winner Prissy (by Unbridled’s Song) and multiple stakes winner Leadem in Ken (by Sky Mesa).
Kitten's First, the dam of Justenuffheart and her siblings, is a winning half sister to United Nations Handicap (USA-G1) winner Down the Aisle (by Runaway Groom). She is out of That's My Hon (by L'Enjoleur), a half sister to 1977 Mother Goose Stakes (USA-G1) winner Road Princess (by Gallant Man; dam of multiple Grade 2 winner Reign Road, by Sovereign Dancer) and 1973 Breeders' Futurity (USA-G3) winner Provante (by Prove It). The next dam in the tail-female line, the Prince John mare One Lane, is out of 1950 Molly Pitcher Handicap winner Danger Ahead (by Head Play), also the third dam of the great Spectacular Bid.
Books and media
Footage of Dreaming of Anna’s win in the 2006 Breeders’ Cup Juvenile Fillies can be accessed at https://www.youtube.com/watch?v=Yf0zhKFc0BE.
Fun facts
Photo credit
Dreaming of Anna prior to the 2008 Beverly D. Stakes at Arlington Park, Garrett Gomez up. Photo taken by Jessica Morgan. Used by permission.
Last updated: December 19, 2025
Race record
17 starts, 10 wins, 3 seconds, 1 third, US$2,024,550
2006:
- Won Breeders' Cup Juvenile Fillies (USA-G1, 8.5FD, Churchill Downs)
- Won Summer Stakes (CAN-G3, 8FT, Woodbine)
- Won Tippett Stakes (USA, 5.5FT, Colonial Downs; new course record 1:01.63)
2007:
- Won Pucker Up Stakes (USA-G3, 9FT, Arlington Park)
- Won Virginia Oaks (USA-L, 9FT, Colonial Downs)
- Won Double Delta Stakes (USA, 8FT, Arlington Park)
- 2nd Queen Elizabeth Invitational Challenge Cup Stakes (USA-G1, 9FT, Keeneland)
- 2nd Gaily Gaily Stakes (USA-L, 8.5FT, Gulfstream Park)
- 3rd Old Hat Stakes (USA-G3, 6.5FD, Gulfstream Park)
2008:
- Won Endeavour Stakes (USA-G3, 8.5FT, Tampa Bay Downs)
- Won Hillsborough Stalkes (USA-G3, 9FT, Tampa Bay Downs)
- Won Early Times Mint Julep Handicap (USA-G3, 8.5FT, Churchill Downs)
- 2nd Churchill Distaff Turf Mile Stakes (USA-G2, 8FT, Churchill Downs)
Honors
Eclipse Award, American champion 2-year-old filly (2006)
Assessments
Highweighted at 123 pounds on the Experimental Free Handicap for American juvenile fillies of 2006, 3 pounds above second-rated Octave.
Topped Canadian-raced juvenile fillies of 2006 on the Canadian Thoroughbred Ratings with 107 pounds.
As an individual
An attractive, refined chestnut mare, Dreaming of Anna had plenty of natural speed and preferred to run on the lead. A good mover, she was game and determined in a drive.
As a producer
Dreaming of Anna produced six named foals of racing age; all six ran and five were winners. Her important foals are as follow:
- All Her Class (2010, by Street Cry) failed to win in three starts but was stakes-placed. She is the dam of Grade 1-placed listed stakes winner With Honors (by War Front).
- Fast Anna (2011, by Medaglia d’Oro) placed in five stakes races including a runner-up finish in the 2014 Ketel One King’s Bishop Stakes. He sired 14 stakes winners from 279 named foals, headed by 2024 American Horse of the Year Thorpedo Anna.
- Dreamologist (2012, by Tapit) won the 2016 Las Cienegas Stakes (USA-G3).
Connections
Foaled in Kentucky, Dreaming of Anna was bred and owned by Frank C. Calabrese. She was trained by Wayne M. Catalano and was ridden to her win in the Breeders’ Cup Juvenile Fillies by Rene Douglas. Dreaming of Anna remained in Calabrese’s ownership throughout her broodmare career. She died of a ruptured aorta on January 9, 2018, at Woodspring Farm, Kentucky.
Pedigree notes
Dreaming of Anna is inbred 4x5 to 1960 American champion juvenile male and 1970 American champion sire Hail to Reason. She is also inbred 5x5x5 to Hail to Reason’s sire, 1953 Garden State Stakes and 1954 Flamingo Stakes winner Turn-to. She is a full sister to multiple Grade 2 winner Lewis Michael and a half sister to multiple Grade 2 winner Justenuffhumor (by Distorted Humor). Dreaming of Anna is also a half sister to Desert Song (by Unbridled’s Song), dam of German listed stakes winner Spanish Honey (by Iffraaj), and to Justenufftime (by Giant’s Causeway), dam of 2014 Monmouth Oaks (USA-G3) winner Cassatt (by Tapit).
Dreaming of Anna and her siblings are out of multiple listed stakes winner Justenuffheart, a half sister to 2004 American champion turf male and two-time American champion sire Kitten’s Joy (by El Prado). Justenuffheart is also a half sister to multiple Grade 1 winner Precious Kitten (by Catienus), dam of 2015 Coolmore Lexington Stakes (USA-G3) winner Divining Rod (by Tapit) and 2020 Endeavour Stakes (USA-G3) winner Jehozacat (by Tapit). In addition, Justenuffheart is a half sister to Striking Image (by Red Ransom), dam of stakes winner Self Made Man (by Catienus). Finally, Justenuffheart is a half sister to Last Kitten (by Catienus), dam of listed stakes winner Prissy (by Unbridled’s Song) and multiple stakes winner Leadem in Ken (by Sky Mesa).
Kitten's First, the dam of Justenuffheart and her siblings, is a winning half sister to United Nations Handicap (USA-G1) winner Down the Aisle (by Runaway Groom). She is out of That's My Hon (by L'Enjoleur), a half sister to 1977 Mother Goose Stakes (USA-G1) winner Road Princess (by Gallant Man; dam of multiple Grade 2 winner Reign Road, by Sovereign Dancer) and 1973 Breeders' Futurity (USA-G3) winner Provante (by Prove It). The next dam in the tail-female line, the Prince John mare One Lane, is out of 1950 Molly Pitcher Handicap winner Danger Ahead (by Head Play), also the third dam of the great Spectacular Bid.
Books and media
Footage of Dreaming of Anna’s win in the 2006 Breeders’ Cup Juvenile Fillies can be accessed at https://www.youtube.com/watch?v=Yf0zhKFc0BE.
Fun facts
- Dreaming of Anna was named in honor of breeder-owner Frank Calabrese’s late sister, Anna Anderson who had died of cancer at the age of 48. A redhead, Anderson was said to have had hair close to the color of the filly’s coat.
- Dreaming of Anna scored her win in the Breeders’ Cup Juvenile Fillies on Calabrese’s 78th birthday.
- Dreaming of Anna received 265 of a possible 270 first-place votes for her Eclipse Award.
Photo credit
Dreaming of Anna prior to the 2008 Beverly D. Stakes at Arlington Park, Garrett Gomez up. Photo taken by Jessica Morgan. Used by permission.
Last updated: December 19, 2025