Vicar's in Trouble is one of two Derby entries for the Ramseys.<br><a target="blank" href="">Order This Photo</a>

Vicar's in Trouble is one of two Derby entries for the Ramseys.
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Anne M. Eberhardt

Multiple Derby Starters Rewards Owners

Ramseys, Starlight, and Skychai continue a tradition of more than one Derby starter.

Difficult as it is to own one Thoroughbred that makes it to the starting gate of the Kentucky Derby, you would think not many owners have started more than one horse in any given Derby. But you'd be wrong.

Ken and Sarah Ramsey, Starlight Racing, and Skychai Racing, all with two starters in this year's Run for the Roses, are merely continuing a trend that is as old as the Derby itself. Either alone or in partnership, at least 128 entities in the Derby's 140 years have had more than one starter in the same Derby.
On eight occasions a single owner has sent three horses to the post, most recently WinStar Farm in 2009. Col. E.R. Bradley managed that feat on two occasions, in 1922 and 1924. But Bradley had the most success when starting two horses: he finished 1-2 with Behave Yourself and Black Servant in 1921 and pulled off that feat again in 1926 with Bubbling Over and Bagenbaggage. In 1932 Bradley won the Derby with Burgoo King while also starting Brother Joe (19th).
Greentree Stable, owned by various members of the Whitney family, also enjoyed success with multiple starters, winning the 1931 Derby with Twenty Grand while Anchors Aweigh and Surf Board ran 10th and 11th; and again in 1942 when Shut Out prevailed and Devil Diver finished sixth.
Brookmeade Farm won in 1934 with Cavalcade while Time Clock ran seventh. Powerful Calumet Farm took the 1948 edition with Citation and ran second with Coaltown. H.P. McGrath started the trend in 1875 when Aristides won the Derby while Chesapeake finished eighth. Andy Crevolin (Determine 1954), King Ranch (Middleground, 1950), Thomas Clay McDowell (Alan-a-Dale, 1902), J.E. Cushing & J. Orth (Lookout, 1893), Overbrook Farm (Grindstone, 1996), Ral Parr (Paul Jones, 1920), J.K.L. Ross (Sir Barton, 1919), Dan Swigert (Baden-Baden, 1877), and Harry Payne Whitney (Whiskery, 1927) have also won the Derby when starting two horses. 
Most recently, the trick has been pulled off by WinStar Farm in 2010 with Super Saver  (American Lion  11th), IEAH Stables in 2008 with Big Brown  (Court Vision  13th), and Lael Stables in 2006 with Barbaro (Showing Up sixth).
The Golden Age of multiple starters in one Derby seems to be the Roaring Twenties. Bradley did it six times in that decade and twice more in the '30s; Harry Payne Whitney also started at least two six times in the '20s, winning with Whiskery in 1927 on the sixth occasion. Joseph Widener started two in 1927.
WinStar, alone or in partnership, carries on the tradition, with two or more starters in 2006, 2008, 2009, and 2010. Other outfits with two recent starters include Zayat Stables (2008), Silverton Hill (2007), Derrick Smith and Michael Tabor (2005), J. Paul Reddam (2007), Tabor (1996, 2005, 2007), Padua Stables (2007), Allen Paulson (1999, 1993), John Oxley (1995), Mike McCarty (2006), Mrs. John Magnier (2002), Robert LaPenta (2010), B. Wayne Hughes (2005), Robert and Beverly Lewis (1995), George & Lori Hall (2009), Dogwood Stable (2000), and Godolphin (2000).
So good luck to the Ramseys, Skychai, and Starlight. It seems the more, the merrier is a common theme on the first Saturday in May.