A Famous Bobby- Not Frankel or Flay, but A Shanghai

Shanghai Bobby’s trademark as a racer was his grit and tenacity down to the wire. The son of Harlan’s Holiday was not afraid to throw down the gauntlet and challenge his rivals to catch him or to withstand his brilliant kick. It did not matter if they were sprinting at 4.5 furlongs or they were running a mile and 1/16th; Shanghai Bobby was not going to relinquish his lead or the victory easily.

That mentality crowned him the 2012 Champion 2YO as voters preferred his culminated campaign over the colt who had come within a head of beating him at the Breeders’ Cup, He’s Had Enough. In a world that’s dominated by who’s in your pedigree, the latter grey colt had the upper hand in that department but could not beat the intangible part of his competitor, as Bobby’s heart just proved too much.

That head may have ultimately made the difference as Shanghai Bobby attracted the legendary farm -and international titan- Coolmore as the handlers of his breeding career, and He’s Had Enough now stands in Florida, despite his champion female family that includes the dams of another exciting sire, Bayern and the late, great Claiborne stallion Arch among many others.

Perhaps unknown to a few, but Shanghai Bobby does share a connection with another (rumored) soon-to-be resident of Ashford: Justify.


While Justify had not even seen a racetrack in the afternoon by the time that Shanghai Bobby had effectively stamped himself as Champion 2YO in the Breeders’ Cup, and Bobby never made it far into his 3YO year, where Justify cemented himself as an immortal with his Triple Crown victory, they shared an owner.

Starlight Racing (while holding the majority share of Bobby and a minority in Justify) can claim both stallions in their racing barn’s glorious history book. It could be argued, as in many cases, that perhaps they would have been treated just as well by Bobby had he not been injured during the running of the Aljiman S. at Belmont Park, but that will be left for the part of history known as “what could have been”. As is the case for many, it’s a section that is notorious for creeping up when you least expect it.

However, while Justify’s breeding future is still just that- in the future, Shanghai Bobby has already experienced some success both in the auction ring and on the racetrack. His offspring include notable runners Gotta Go, March X Press, and Mr. Pete and his presence in South America is being felt with his 2YOs running up the tally boards in Brazil as Group I winners in their respective country. Buyers aren’t running as quickly for his yearlings, but they consistently sell in the middle to high six digit range while bringing positive remarks from a wide variety of people.

Now, Bobby’s female family was mentioned above and it got a bit of a negative ring when being compared to He’s Had Enough’s dams and granddams. While the mares of the Bobby family may have lacked immediate brilliance, they go back to a proud racing tradition that includes a Triple Crown winner and some of the most recognized names in racing. This part is just a fun trip down history courtesy of Shanghai Bobby.

His dam, Steelin’, raced 25 times and finished in the money in eleven of those starts. She didn’t produce many other runners or breeders of notice (outside of Bobby) and records indicate there were only four foals at the time of this article. Her dam, Steel Band, did even worse than that while having seven foals, and not one being of enough importance to justify a mention in the stallion register. Ouch.

The great great granddam is where the family gets most of its register page black-type, as Wedding Band produced twelve foals that eventually gave rise to stakes winner City Band and that daughter in turn contributed to the genes of Foolishly, Weather Warning, American Lion, St. Liam’s Halo, and Freedom Child. Wedding Band was eventually sent to Japan to breed for a bit before making another international trip to Australia in 2004, where she stayed presumably until her death.

We jump to the 5th dam and we find Spinning Reel. Bred in Kentucky and a winner of her career debut (and only start), she went on to have 14 foals with five retiring at the end of their careers with the coveted black-type. While she was known for her breeding prowess, her dam Spinning Top was the racing attraction for her owner, John S. Phipps. She garnered victories in the Black Eyed Susan and Vineland Handicap while also producing strong showings in the Top Flight Handicap (two years in a row) and in the Firenze Handicap at the long closed and demolished Jamaica Racetrack.

As we travel back, the racing and breeding talent becomes more potent as we now find Whirlabout, who raced and won every year from ages 2 to 5. She made 51 starts for part owner and breeder Arthur B. Hancock, Jr. with some of those 17 wins being in the Gazelle, Test, Debutante, and Santa Barbara Stakes. Remarkably, she finished her career being on the board 35 times; the average career now doesn’t even beat her win count.

Dustwhirl- Dam of Whirlaway Photo Belong to Owner, All Rights Reserved

Finally, on the last stop of the historical tour, we find Dustwhirl. Born in 1926, with no starts, no white markings on her body (from what limited black and white pictures of her show) and no real reason to stand out, why did she? This bay mare was the dam of the fifth Triple Crown winner, Whirlaway.

The colt was by the English Derby winner Blenheim, and came into the world April 2nd, 1938. Dustwhirl was purchased from Arthur B. Hancock while Whirlaway was still in-utero for $12,000 (about $212,404 now) and her now legendary son was campaigned to his Triple Crown triumph by the storied Calumet Farm. She died in 1946, and “Mr. Longtail” joined her on the other side just seven years later at the age of 15.

While the genetics this far back in his pedigree have no impact on Shanghai Bobby now, it is interesting to see how gradually things began to change. Some records invariably were lost to time, but Bobby descends from a very noble tradition of racing and breeding excellence. He has a Triple Crown producing mare in his pedigree, his owners are blessed with a Triple Crown winner, and his sire even has a Triple Crown winner in his family as Harlan’s Holiday’s dam is the daughter of Affirmed and Harlan’s Holiday’s sire line contains Secretariat, perhaps the most famous and talented winner of them all.

Shanghai Bobby doesn’t have just looks on his side, but heart, genetics, and history look kindly upon a stallion that is just starting to get warmed up as a sire. The future looks bright for the nearly black descendent of Triple Crown glory.

3 replies »

  1. Very nice analysis. I was never a huge fan of this horse, when he ran. I saw him at Coolmore, and he is a very nice looking stallion.


    • I love him now and loved him then, as he was my first Breeders’ Cup experience in person! I will always have a soft spot for Shanghai Bobby. He got sparkling reviews when I saw him at the open house and the manager who was there speaking to breeders at the time could not say enough good things about him. I even believe Bobby was called “one of the nicest and most consistent Harlan’s Holidays that he [the manager] had ever seen”. Apparently, the most recent book of mares was amazing and they are expecting very nice foals this year. Maybe we’ll see a bit more of this once the yearling photos are released before the September sale.

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      • Yeah, this Shang Shang Shang and your article likely will change my mind about him. I loved his sire as well. Bobby is a very beautiful sire. 🙂