Foaled in 1997, Darling My Darling was a good race mare on her own account, running second in the Matron Stakes (USA-G1) and Frizette Stakes (USA-G1) as a juvenile. At 3, she won the listed Raven Run Stakes at Keeneland, clicking off seven panels in a swift 1:20.88, and at 4 she added the Doubledogdare Stakes, also at Keeneland, at a mile and one-sixteenth.
Sired by two-time American champion sire Deputy Minister (the 1981 Canadian Horse of the Year and American champion 2-year-old male), Darling My Darling was produced by the Mining mare Roamin Rachel, making her a half sister to 2004 Japanese Horse of the Year Zenno Rob Roy (by Sunday Silence). Darling My Darling is also a half sister to Stray Cat (by Storm Cat), dam of Japanese Group 3 winners Cat Coin (by Stay Gold), One Breath Away (by Stay Gold), and Rock This Town (by Orfevre) as well as Japanese listed stakes winner Tagano Elisabeth (by Special Week).
Roaming Rachel was probably the best runner sired by the brilliant but unsound 1988 Vosburgh Stakes (USA-G1) winner Mining. Like her sire, she could pick ‘em up and put ‘em down, picking up the marquee score of her career in the 1994 Ballerina Handicap (USA-G1). A full sister to Canadian restricted stakes winner Hello Rachel and to Choice Claim, dam of 2001 First Lady Handicap (USA-G3) winner Another (by Seattle Slew), Roaming Rachel is also a half sister to Tangled (by Linkage), dam of 1995 Acorn Stakes (USA-G1) winner Cat’s Cradle (by Flying Paster), Roamin Rachel is out of the unraced Clever Trick mare One Smart Lady, whose dam Pia’s Lady (by the top-class handicapper Pia Star) also produced stakes winner Not Tomorrow (by Moonsplash).
Darling My Darling produced two good fillies on her own account to matings with stallions from the A.P. Indy male line. The elder, Forever Darling (by Congrats), won the 2016 Santa Ynez Stakes (USA-G2) and is the dam of Forever Young, who has the UAE Derby (UAE-G2) and Saudi Derby (KSA-G3) to his credit along with his Kentucky Derby third. The younger, Heavenly Love (by Malibu Moon), won the 2017 Darley Alcibiades Stakes (USA-G1) and is the dam of Sierra Leone (by Gun Runner), who came into the Run for the Roses off wins in the Toyota Blue Grass Stakes (USA-G1) and Risen Star Stakes (USA-G2). Darling My Darling is also the dam of Sky My Darling (by Sky Mesa), dam of multiple Brazilian Group 3 winner Charles Do Bronxs (by Carrocel Encantado).
Darling My Darling’s last name foal is Lovely Darling, an unraced 2021 filly by Flameaway, but both Forever Darling and Heavenly Love remain in production. The former produced a 2022 filly by Kizuna and a 2023 filly by Epiphaneia, while the latter is the dam of the unraced 2022 Nyquist colt Domestic Policy and a 2024 filly by Gun Runner. As for the participants in Darling My Darling’s double of Derby placers, they will undoubtedly be heard from again later in the year, though perhaps in not such dramatic fashion as when they nearly kept the Kentucky Derby all in the family.