courtesy WinStar FarmHarlan's Holiday Shanghai Bobby did not come out of nowhere to win the Eclipse Award—after all, he hails from the most powerful barn in America, that of trainer Todd Pletcher. But from a pedigree standpoint, Shanghai Bobby does not hail from a family of proven stock… and so, as the saying goes, he will have to make his own pedigree. So far, so good. Shanghai Bobby is the first foal of the Orientate mare Steelin’.  Her produce record may turn out to be good or great, especially since she figures to be bred to top sires in future years. But other stakes winners in his family are far and few between. On the male-line side, Harlan’s Holiday, the sire of Shanghai Bobby, is by no means obscure or average. In fact, he was the leading juvenile sire in 2012, setting a single-season record for progeny earnings. His reputation as a sire is ascending and his progeny have been valued at sales. The 70 yearlings by Harlan’s Holiday that sold at public auction last year averaged $87,745. Harlan’s Holiday is a son of Harlan, who initially stood for $5,000 and died with just 102 foals left behind. One turned out to be Grade 1 winner Menifee. His other Grade 1 winner was Harlan’s Holiday. As a racehorse, Harlan’s Holiday immediately made an impression, being a graded stakes winner at two, and then went from strength to strength as the distances increased at age three. He won the 2002 Florida Derby and Blue Grass Stakes and was one of the favorites in the Kentucky Derby, but he could only finish seventh on War Emblem’s day at Churchill Downs. He was a consistent runner, though, and he came back to excel later that year and as a 4-year-old, winning the Grade 1 Donn Handicap in 2003 and finishing second in that year’s Dubai World Cup. He won nine of 22 starts, with six seconds, and earned $3,632,664. Harlan’s Holiday retired in 2004 to Airdrie Stud in Midway, Ky., at a fee of $17,500. In his first crop, he sired Grade 1 Hollywood Futurity winner Into Mischief, and finished the season second to Posse on the freshman sire list. Into Mischief has reflected well on Harlan’s Holiday by becoming the third-leading freshman sire of 2012 and siring current Kentucky Derby points leader Goldencents among three stakes winners from his initial crop. Harlan’s Holiday has been a steady sire, getting 34 stakes winners from 565 foals of racing age (six percent) through last year, with 14 graded stakes winners. He has three Grade 1 winners to date: Shanghai Bobby, Into Mischief, and Majesticperfection; plus Grade/Group 2 winners Willcox Inn and Mendip, among others. Harlan’s Holiday moved to WinStar Farm in Versailles, Ky., for the 2011 breeding season, and his stud fee this year will be $35,000. He is expected to cover a book of 150 mares. He has 117 two-year-olds of 2013. Shanghai Bobby hails from a female family that has produced only two Grade 1 winners in the first three dams. His dam, Steelin’, raced on the Southern California circuit and was a stakes winner of $185,197, taking the Bangles and Beads Stakes at Fairplex Park. Steelin’ was the only successful racehorse from her dam, the Carson City mare Steel Band, who produced just the one winner from six foals, four to race. Steel Band was only placed herself, but was given a chance in the breeding shed because she was a full sister to Grade 1 winner City Band. City Band won the 1996 Grade 1 Oak Leaf Stakes and the Grade 3 Golden Rod Stakes and earned $607,419. City Band produced Canadian stakes winner Weather Warning and Charles Town stakes winner Foolishly, and she is the granddam of 2010 Illinois Derby winner American Lion and Canadian stakes winner St Liams Halo. And that’s it. No other mare in the first three dams has produced a stakes winner. When Shanghai Bobby, bred by Stonehaven Steadings, was offered at the 2011 Keeneland September yearling sale, Frank Brothers saw something that he liked and went to $105,000 to purchase him as agent for Starlight Stable. It was more than four times Harlan’s Holiday’s stud fee at the time, and worth every penny. To read more about Shanghai Bobby's Eclipse Award-winning season, click here.