The feat was accomplished by Hanley Webb in 1924 with Black Gold and by Ben A. Jones who did it twice, first with the great Citation in 1948 and then with Hill Gail in 1952.
[4] Since Tim Tam, the gradual trend in training has been toward giving Derby contenders fewer prep races and more time between them.
In recent years, the Trial has sent the Preakness such horses as Key to the Mint (1972), No More Flowers (1987), Houston (1989), Honor Grades (1991), Alydeed (1992), Cherokee Run (1993), Numerous (1994), Our Gatsby (1995), Black Cash (1998), Patience Game (1999), Sir Shackleton (2004), Flying First Class (2007), Macho Again (2008), and Pleasant Prince (2010).
And two of trainer Woody Stephens' Trial winners Caveat in 1983 and Creme Fraiche in '85 went on to win the Belmont Stakes (GI).
In 1967, Barb's Delight became the last Trial horse to have a significant impact on the Derby, finishing second by a length to longshot Proud Clarion.
Most notable of those were Calumet Farm's Iron Liege, who finished fifth in the Trial and returned to defeat a Kentucky Derby field that included champions Gallant Man, Round Table and Bold Ruler and is generally considered to be the greatest field in Derby history.
King Ranch's Assault finished fourth in the Trial, but returned to win the Derby and sweep the Triple Crown.