Stilleto Boy is the best of nine winners out of Rosie's Ransom (Marquetry), who has produced three stakes performers, with Stilleto Boy clearly the best. She is also the dam of the Listed winner Rosie My Rosie (Purge) and of Condo Closing (Offlee Wild), twice Listed-placed. Rosie's Ransom is a half-sister to the Listed-placed Grandelena (Grand Slam) and to the winner Ama De Casa (Grand Slam), dam of the Listed-placed Diego.

Second dam Gold Ransom (Red Ransom) was unraced. She is a full-sister to Lulu's Ransom, a multiple Listed winner who was Grade 3-placed.

Third dam Flaming Gold (Storm Bird) was unraced.

Stilleto Boy is the first graded winner from his immediate female family. A distant relative is Typecast (Prince John), champion older mare in 1972.

Rosie's Ransom's latest reported foal is the 2-year-old colt Irish Ransom (Gormley).