Shackleford held off a late-charging Animal Kingdom in the stretch to win the Preakness Stakes, the second race in the Triple Crown held May 21 at Pimlico Race Course in Baltimore, Md. The 3-year-old son of Forestry is a homebred for Mike Lauffer and William Cubbedge. He was ridden by Jesus Castanon and trained by Dale Romans.

As anticipated, the pace was much faster than in the Kentucky Derby–held May 7 at Churchill Downs in Louisville, Ky.–where Shackleford led the field through early fractions of :23.74, :48.63, and 1:13.40. Shackleford wound up finishing a respectable fourth behind Animal Kingdom, Nehro, and Mucho Macho Man.

On May 21 at Pimilco, however, a solid pace was set by Flashpoint, a son of Pomeroy, who clicked off the first three-quarters of a mile in :22.89, :46.87, and 1:12.01.

Shackleford set just behind Flashpoint after the start and stayed there through the first turn and all the way down the backstretch. Stalking behind the front-runners were Midnight Interlude and Dance City. The winner took the lead going into the second turn and swung into the stretch about three paths off the rail