Robert Hill-Smith, chairman of the renowned Australian winery Yalumba and a figure with deep family ties to South Australian horse racing, is currently experiencing the unpredictable nature of thoroughbred breeding through his promising two-year-old colt, Bootlegger. Despite being passed in at auction below his reserve price, Hill-Smith chose to retain Bootlegger, a son of the notable sire Too Darn Hot, bred from the mare Princess Youmzain. Bootlegger has shown early promise with a maiden win at Gawler and has attracted overseas interest, though Hill-Smith prefers to continue racing the colt for enjoyment rather than immediate financial gain.

The South Australia Sires’ Produce Stakes, recently repositioned as a Group 3 event to highlight late-developing juveniles, has drawn strong competition including Bootlegger and other notable horses like the unbeaten Volkano. Hill-Smith remains cautiously optimistic about Bootlegger’s future, acknowledging the challenges ahead but hopeful that the colt will realize his potential over the coming 18 months. The race and Hill-Smith’s involvement underscore the enduring legacy and ongoing passion for racing within his family and the South Australian racing community.