The question posed to jockey Julien Leparoux Tuesday is one with which many in the Thoroughbred racing world have wrestled. As the 10-time leading rider at Keeneland began his answer, his agent, Steve Bass, interjected with some blunt truth.
"You want to know the key to beating Wise Dan?" Bass asked rhetorically in reference to the two-time defending Horse of the Year and 10-time Grade I winner. "The way to beat Wise Dan is if Wise Dan beats himself somehow. That's the only way. He finds ways to win."
Leparoux knows this, having ridden Wise Dan half a dozen times earlier in the champion gelding's career. When Leparoux pilots Sayaad against the six-time Eclipse Award winner in Saturday's Grade I, $1 million Shadwell Turf Mile at Keeneland, he and six other challengers will do all they can to have their best possible outing on the chance the future Hall of Famer is less than his typical superior self.
After Wise Dan underwent emergency colic surgery at Rood and Riddle on May 16, there were the inevitable questions of whether he could return to races with his freakishly efficient step at 100 percent.
The 7-year-old gelded son of Wiseman's Ferry settled that issue, notching a nose victory over fellow Shadwell entrant Optimizer in the Grade II Bernard Baruch Handicap at Saratoga on Aug. 30, his first test since going under the knife.
Upon returning to his Keeneland base, Morton Fink's homebred has methodically touted himself to anyone witnessing his morning routine. There was the bullet 5-furlong move in :59.40 on the main dirt track on Sept. 13, the handy five-eighths work in 1:01.20 over the turf on Sept. 23 and on Monday, a strong gallop most horses would be hard pressed to match in timed workouts.
"I tell you he's on top of his game right now," said Wise Dan's trainer, Charlie LoPresti. "We gave him a long, strong gallop (Monday) and he was clicking off 12s and 13s at every pole. He's bouncing and seems real happy. I don't know how you can get him any better than he is right now.
"After everything he's been through this year, I kind of wondered myself when we went to Saratoga ... is he the same horse? Is that surgery going to take something out of him? And then you start thinking well, he's 7 years old, when will he start losing a step? Then he does what he does (Monday). And he does what he did on the grass last week and he gallops out :59 and change on the dirt. He just amazes me."
The Grade I Shadwell — Keeneland's first stakes to carry a $1 million purse — was won by Wise Dan in 2012 and anchors a Saturday card that features five graded stakes, including the Grade I Claiborne Breeders' Futurity for 2-year-olds and the Grade I First Lady for fillies and mares going 1 mile on the turf.
Last year's Shadwell Mile marked the lone defeat for Wise Dan in seven starts in 2013 and his first loss since running second in the 2012 Grade I Stephen Foster at Churchill Downs. When a deluge of rain soaked the area, last year's Shadwell was taken off the turf and contested at 11⁄16 miles over the synthetic Polytrack, conditions Dale Romans-trainee Silver Max relished as he upset Wise Dan in gate-to-wire fashion.
Silver Max is back to try for another shocker this year, but is coming off a last-place finish in the Grade II Fourstardave Handicap at Saratoga on Aug. 9. Still, the son of Badge of Silver figures to be the main speed again, although potential soft turf due to expected rain on Friday could hinder him.
"I don't ever write any horse off. I'm not taking anything for granted," LoPresti said. "But I'm happy where I'm at with (Wise Dan). He's fit enough. It just depends on the trip and how it unfolds."
Wise Dan will break from post No. 6 under jockey John Velazquez in the eight-horse field with his expected main challenger, fellow Grade I winner Seek Again, in the outside post under Joel Rosario.
The winner of the 2013 Grade I Hollywood Derby, Seek Again came within a head of defeating Wise Dan when he ran second to the two-time Breeders' Cup Mile winner in the Grade I Woodford Reserve Turf Classic at Churchill Downs this May 3.
Juddmonte Farms' homebred son of Speightstown has continued to improve, winning the Grade II Fourstardave in course-record time.
While Seek Again's athleticism and ability to run the turns has particularly impressed his connections, there is fear that they are all running headlong into the mouth of a reawakened monster.
"I feel very confident (Seek Again) will run his race," said Juddmonte Farms manager Garrett O'Rourke. "... The only thing that concerns me is the Wise Dan that shows up, and my reports that I'm getting is that the Wise Dan of old might be back. If he is, that scares me."