One of the biggest winners of the Kentucky Derby and Oaks weekend didn’t run a horse in either of the marquee races. Sheikh Mohammed al-Maktoum’s Darley America picked up another big win for its stallion roster Friday when Cathryn Sophia, a daughter of Street Boss, drew away to win the Kentucky Oaks. The following day, future Darley resident Nyquist took home the roses as the favorite in the Kentucky Derby. “It was a special weekend,” said Dan Pride, chief operating officer of Darley’s U.S. base in Lexington, Ky. “Sheikh Mohammed bought Jonabell Farm back in 2001 and started the stallion operation in 2002, and this would be right in the bull’s-eye of the game plan for him – having horses sired by his stallions and being future stallions in the biggest races in America. Certainly, the Oaks and Derby are the pinnacle of those goals.” The champion Nyquist’s Derby victory added to the likely dividends from what was already a shrewd investment by Darley. Pride said terms were reached with owner J. Paul Reddam to secure Nyquist’s breeding rights last October, prior to the Uncle Mo colt’s win in the Breeders’ Cup Juvenile at Keeneland. “It was very quick,” Pride said. “Mr. Reddam ran Gomo in the Alcibiades, which we sponsored, so Mr. Reddam was at the race that day, and Nyquist was the topic of conversation. It was a very uncomplicated process. Mr. Reddam was open to receiving offers, so we were in a position to make one, and luckily for us, he picked us.” Nyquist would be the third Kentucky Derby winner on the active roster at Darley, joining 2007 winner Street Sense and 2011 winner Animal Kingdom. Nyquist and Street Sense are also the only two horses to win the Breeders’ Cup Juvenile and Kentucky Derby. In assessing Nyquist as a stallion prospect, Pride said the three biggest variables were pedigree, race record, and conformation. At the time the two sides began negotiations, Nyquist was already a two-time Grade 1 winner, and Gomo picked up a Grade 1 victory in the Alcibiades, both key parts of Uncle Mo’s record-breaking first crop of juveniles. As for conformation, Pride said Nyquist’s three successful trips through the auction ring were a ringing endorsement. “He sold as a weanling, yearling, and 2-year-old, and each time he made money for the person who sold him, and that doesn’t always happen,” Pride said. “He increased in value, and that gives you confidence in what people think about the profile of the horse and what he looks like on the shank.” Terms of the agreement are confidential, but Pride said that Reddam and Darley management would meet following this year’s Breeders’ Cup to determine whether to begin Nyquist’s stallion career or race him at age 4. Among the stallions Nyquist will join upon his retirement is Street Boss, who picked up perhaps his biggest résumé boost with Cathryn Sophia’s Oaks win. It’s easy to fly under the radar in a group of sires that includes champions, classic winners, and sires of Hall of Famers. Street Boss stands for the farm’s third-lowest advertised fee of $12,500. Make no mistake, Street Boss holds his own. The 12-year-old son of the late Darley stallion Street Cry is a multiple Grade 1-winning sprinter with five crops of racing age, 231 winners, and progeny earnings in excess of $18.7 million. Cathryn Sophia was the third North American Grade 1 winner for Street Boss, following Capo Bastone and Danza, who finished third in the 2014 Kentucky Derby. Street Boss is the first Darley stallion to sire a Kentucky Oaks winner as a resident of Sheikh Mohammed’s operation, with Medaglia d’Oro conceiving 2009 winner Rachel Alexandra and 2011 winner Plum Pretty prior to being acquired by Darley. “I remember watching him run, and Bruce Headley co-owned him and trained him and focused on those one-turn six- and seven-furlong races,” Pride said. “He’s built more like a sprinter. He’s got a beautiful profile but looks more like a one-turn sire, so for him to get an Oaks winner, that’s what you want.” Street Boss is also a frequent shuttler to Darley’s Australian base, where his runners include Group 1 winner The Quarterback. “If you look at him in Australia, he’s going from $10,000 Australian last year and he’s at $25,000 this year,” Pride said. “They’re selling seasons already for him for the Southern Hemisphere season, and he’s already booked full or close to it before Cathryn Sophia happened. His demand and interest in him is going to continue to increase. If he keeps on with the Cathryn Sophias of the world, it’ll get people’s attention.”