The winner of the Natalma Stakes (CAN-G1) at 2, when she was Canada's champion juvenile filly, Lady Speightspeare is a descendant of Heatherglow, an unraced daughter of The Axe II x Brilliantly, by Hill Prince. As a broodmare prospect, Heatherglow's primary attraction was her pedigree: She is a direct female-line descendant of La Troienne through the important matrons Baby League, Striking, and Glamour, and is inbred 4x5 to the great matriarch. She is also 3x5 to Blenheim II and 4x5 to another great foundation mare, Mumtaz Mahal, through the three-quarters siblings Mahmoud (sire of The Axe II) and Mumtaz Begum (dam of Glamour's sire Nasrullah).
For all of her regal heritage, Heatherglow was solid but unspectacular as a broodmare, perhaps in part because she spent half her breeding career being put to sires that were no more than second-tier. While she produced nine winners from 11 named foals, her only black-type runner was Canonization, whose sire Native Heritage (by Raise a Native) won a modest stakes as a juvenile. Third in a minor stakes at Hollywood as a 4-year-old, Canonization represented an outcross away from her dam's inbreeding, though her pedigree sports a 5x5 cross to Blue Larkspur.
After producing three undistinguished winners for her owner-breeder, Harbor View Farm, Canonization was sent to the 1985 Fasig-Tipton November mixed sale in foal to Native Royalty, changing hands for US$20,000. The foal she was carrying, Host of Royalty, was also nothing special, and her new owner, Irish Acres Farm, sent the mare to two-time Washington Park Handicap (USA-G3) winner That's a Nice to produce a foal for the Illinois-bred program.
That foal turned out to be more than anyone could have reasonably expected. Named Lady Shirl, she became an Illinois-bred restricted stakes winner at 3 in the Anita Peabody Handicap at Arlington Park and then blossomed at 4 to win six stakes events, three of them graded. Her biggest win was in the 1991 Flower Bowl Handicap (USA-G1). She won two more listed stakes as a 5-year-old and at 6 scored her last stakes win by taking her third edition of the Anita Peabody, which she had also won at 4. She retired after four starts at age 7 with 18 wins and 12 placings from 41 starts and earnings of US$951.523.
While Lady Shirl was a Grade 1 winner, she was not a picture horse and had an offbeat pedigree. She may also have been stigmatized by the myth that hard-raced mares make poor broodmares, as she was a US$190,000 RNA from the 1995 Keeneland January sale. By the time of the 1998 Keeneland November sale, her perceived value (plus that of an unborn foal by Victory Speech) had declined to US$110,000, and at the 2000 Keeneland November sale, she changed hands again for US$90,000, this while in foal to Theatrical. Five years later, she went through Keeneland November once more, again in foal to Theatrical, and went for US$485,000 in spite of the fact that she was 18 years old. The reason for her marked upswing in price was her 2001 Theatrical colt. Named Shakespeare, he won the 2005 Joe Hirsch Invitational Turf Classic Stakes (USA-G1) and Belmont Breeders' Cup Handicap (USA-G2) before disappointing badly in the 2005 Breeders' Cup Turf (USA-G1), the only race of his career that he did not win. He later added the 2007 Woodbine Mile Stakes (CAN-G1) to his trophy case before retiring to a disappointing stud career.
Charles Fipke, never shy about making unorthodox moves in his breeding program, was Lady Shirl's buyer on her last trip through the sale ring, and the following spring, she produced Shakespeare's full sister Lady Shakespeare. Winner of the listed Ontario Colleen Stakes at 3, she improved from 3 to 4 as her dam and brother had and won the 2010 New York Stakes (USA-G2) and Grey Goose Bewitch Stakes (USA-G3). She was succeeded by her year-younger half-sister Perfect Shirl, the result of a mating between Lady Shirl and Fipke's homebred Canadian champion turf horse, 2003 Shadwell Turf Mile Stakes (USA-G1) winner Perfect Soul (by Sadler's Wells). All Perfect Shirl did was win the 2010 Lake George Stakes (USA-G2) at 3 and then upset the 2011 Emirate Airlines Breeders' Cup Filly and Mare Turf (USA-G1) at 27-1 odds.
Both Perfect Shirl and Lady Shakespeare are now Grade 1 producers, with Perfect Shirl having produced 2021 Maker's Mark Mile Stakes (USA-G1) winner Shirl's Speight to a cover by Speightstown. Lady Speightspeare is very similarly bred as she is Speightstown's daughter from Lady Shakespeare, now the dam of four winners. Lady Shakespeare's most recent foals are Ready Shakespeare, an unraced 2-year-old colt by More Than Ready, and a 2021 filly by Bee Jersey. Her most recent mating was to Perfect Soul for a 2023 foal.
Young mares generally carry a premium in the sale ring, but it is worth noting that Lady Shirl produced her graded stakes-winning offspring when she was 14, 19, and 20, as well as throwing restricted stakes winner Fantastic Shirl (by Fantastic Light) when she was 16. From Canonization onward, though, this has been a family that has generally shown its best with maturity. If that pattern holds true with Lady Speightspeare, look for her to add further graded races and perhaps another Canadian championship to her record before she attempts to emulate the feats of her granddam, dam, and "aunt" in the paddocks.