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On This Date in Sports May 1, 1999: Charismatic

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Charismatic, a 31-1 longshot ridden by Chris Antley, wins the Kentucky Derby by a head over Menifee. The win was the fourth Derby win for trainer D. Wayne Lucas and denied Bob Baffert a third straight win, despite having three contenders who were non-factors at the end of the race. Charismatic would win the Preakness but pulled up in the Belmont, missing the Triple Crown.

The 125th run for the roses saw a crowded field with 19 horses entered. After leading Silver Charm to victory in 1997 and Real Quiet to victory in 1998, all eyes were on trainer Bob Baffert who had three strong contenders in the race with Excellent Meeting, General Challenge, and Prime Timber.

Nobody gave much of a chance to Charismatic, who starting in the 16th gate, had been listed at 31-1 to win the race. The horse had a good pedigree being the Squire of Preakness winner Summer Squall. Struggling most of the season, Charismatic did not show any promise until he captured the Lexington Stakes two weeks earlier.

When the race started, Valhol, ridden by Willie Martinez, broke in front early, setting a slow pace in front of Cat Thief with Mike E. Smith in the saddle. Charismatic spent most of the race in the middle of a crowded field but began making his move after three-quarters of a mile. As the race hit the final stretch, Charismatic, with his rider, Chris Antley, passed Cat Thief to take the lead. Over the final furlongs, Pat Day made a late charge with Menifee but could not catch Charismatic, who won the race in a time of 2:03.29, winning by a head over Menifee, as Cat Thief ended up in third. Bob Baffert’s trio of contenders ended up not being much of a factor as Prime Timber, ridden by David Flores, finished fourth, Excellent Meeting, ridden by Kent Desormeaux, finished fifth and General Challenge, finished in 11th place.

Two weeks late,r Charismatic was still not listed as a favorite as he battled Menifee again in the Preakness Stakes. Posting a time of 1:55.20, Charismatic won the second jewel of the Triple Crown, finishing a length and a half in front of Menifee, the favorite in Baltimore. Charismatic finally was a favorite in the Belmont Stakes, looking to be the first horse in 21 years to win the Triple Crown. History appeared to be within grasp as Charismatic led into the final stretch, but Jockey Chris Antley pulled up, allowing Lemon Drop Kid to pass in the last on the eighth mile to win in New York as Vision and Verse finished second. After Charismatic finished third, Antley quickly dismounted and held his horse, realizing he suffered an injury. If not for the jockey’s quick actions, the injury could have been fatal to Charismatic, but surgeons were able to repair the fractured front left leg. Despite never racing again, Charismatic was named Horse of the Year in 1999.