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Shanghai Bobby
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Shanghai Bobby Clear Leader Among 2YO Males

He'll shine at Breeders' Cup but his pedigree raises questions about the classics.

While the standings in most of Thoroughbred racing's other divisions are still in flux, the juvenile male division appears to have a clear leader, at least in the East. Now unbeaten in four starts, Starlight Racing's Shanghai Bobby  staked his claim to favoritism in the Grey Goose Breeders' Cup Juvenile (gr. I) with a visually impressive win in the Foxwoods Champagne Stakes (gr. I) on Oct. 6.

Bred in Kentucky by Stonehaven Steadings, Shanghai Bobby is one of 12 stakes winnersfour of them of graded caliberrepresenting WinStar Farms stallion Harlan's Holiday in 2012. Ranked 19th on the general sire list (as of Oct. 8), Harlan's Holiday leads the juvenile sire list by earnings and number of stakes winners with four. To date, Harlan's Holiday has sired 288 winners (51.2%) and 33 stakes winners (5.9%) from 563 foals of racing age. The best other than Shanghai Bobby have been grade I winners Majesticperfection  and Into Mischief ; the latter-named horse, a freshman sire of 2012, is the sire of Champagne Stakes runner-up Goldencents.

Produced from the Affirmed mare Christmas in Aiken (a granddaughter of 1968 Hollywood Gold Cup heroine Princessnesian), Harlan's Holiday is the leading runner and sire for the late Harlan, a son of Storm Cat whose chief victory came in the 1994 Vosburgh Stakes (gr. I) as a 5-year-old. As a late-maturing sprinter, Harlan was not well patronized by breeders, getting just 102 named foals before dying in 1999, but his six stakes winners included two very good middle-distance runners in Harlan's Holiday and Menifee. While both were from mares that could reasonably be expected to contribute some stamina, both also probably benefited from the fact that Harlan was out of Country Romance, a stakes-winning daughter of the staying Halo.

A grade III winner as a juvenile, Harlan's Holiday came into his own in the spring of 2002, winning the Florida Derby (gr. I) and the Toyota Blue Grass Stakes (gr. I). He was made the favorite for the Kentucky Derby (gr. I) off those efforts but finished seventh, and his only other win at 3 was in the Pennsylvania Derby (gr. II). At 4, Harlan's Holiday won the Donn Handicap (gr. I) and was runner-up in both the Dubai World Cup (UAE-I) and the Hollywood Gold Cup (gr. I) before suffering a tendon injury while finishing last in the Saratoga Breeders' Cup Handicap (gr. II). He entered stud at Airdrie Stud in 2004 and was second to Posse on the freshman sire list in 2007, third on the second-crop sire list in 2008, and fifth on the third-crop list in 2009.

Shanghai Bobby is the first foal of the stakes-winning Orientate mare Steelin', who earned her black type by winning the 2008 Bangles and Beads Stakes at Fairplex as a 4-year-old. Orientate himself was of much higher class, winning the Breeders' Cup Sprint (gr. I) and five other stakes of 2002 on his way to a title as that year's champion sprinter. At stud, Orientate has gotten plenty of winners (to date, 360 of his 643 foals of racing age) but has been more uneven in terms of quality. Somewhat surprisingly, his top earner has been the 2007 Alabama Stakes (gr. I) winner Lady Joanne, and he is also the sire of 2011 Sky Classic Stakes (gr. IIT) winner Kara's Orientation, demonstrating his ability to get horses capable of staying 10 furlongs. But his other two grade/group I winners, 2008 Eclipse Award finalist Intangaroo and the Argentine-based Lady Sprinter, have been more what one might expect with their major successes coming at sprint distances. Shanghai Bobby is Orientate's first graded winner as a broodmare sire.

Steelin' was produced from the Carson City mare Steel Band, a full sister to 1996 Oak Leaf Stakes (gr. I) winner and multiple stakes producer City Band. As Carson City (a multiple graded stakes-winning sprinter) was produced from a daughter of 1976 French champion juvenile and 1977 English and French champion miler Blushing Groom, also the paternal grandsire of Orientate via his good sire son Mt. Livermore, Steelin' is inbred 3x4 to Blushing Groom through lines that suggest high-class speed rather than stamina.

That might lead to suspicions that Shanghai Bobby may not want distances much greater than a mile, and Steel Band's dam Wedding Band would tend to support that hypothesis. Sired by 1984 Remsen Stakes (gr. I) and Laurel Futurity (gr. I) winner Mighty Appealing (by Valid Appeal), who failed to train on at 3 despite his successes over routes at 2, Wedding Band was an unbeaten juvenile in four races over sprint distances at 2 but managed only one more win while racing through age 4. The closest influence for stamina along Shanghai Bobby's female line is 1966 champion turf male Assagai, sire of Wedding Band's dam Ring of Light.

Given that Harlan's Holiday appeared to be a better horse at nine furlongs than at 10, Shanghai Bobby may find the 10 furlongs of the Kentucky Derby Presented by Yum! Brands a reach. Nonetheless, the colt has done everything asked of him to date without ever being pressed for his best, and that bodes well for a trip to Santa Anita Park and a shot at this year's juvenile championship.