Ron Winchell, who campaigns Louisiana Derby (G2) runner-up Midnight Bourbon in the name of his family’s Winchell Thoroughbreds, said he’s trying to keep his enthusiasm in check about their chances in Saturday’s 146th Preakness Stakes (G1) at Pimlico in Baltimore.

Winchell is the co-owner and co-managing partner of Franklin’s Kentucky Downs with Marc Falcone. He’s also a Las Vegas entrepreneur as well as an internationally prominent owner and breeder.

“It’s hard not to be overly optimistic,” Winchell said by phone. “He’s doing great. The Derby didn’t seem to take a lot out of him.”

Midnight Bourbon finished a late-running sixth in the May 1 Kentucky Derby (G1) after an awkward start took the strapping, nearly-black colt out of his normal up-close running style.

His connections knew the son of Tiznow was in trouble early on in the Derby. With the scratch of King Fury, the Steve Asmussen trainee went from being one of the last horses to load to one of the first, having to stand in the gate while the others were led in. When the gate’s stall doors sprung open, his hind end slipped out from under him, taking Midnight Bourbon out of a preferred position up on the pace or just off the leaders. Instead, he found himself as far back as 14th and wide on both turns before rallying.

“I said it before the race, ‘If he doesn’t come by the first time and he’s not in the first five or six spots, we’re pretty much toast,’” Winchell said. “That’s just how the Derby seems to be working out now.”

Winchell doesn’t have to look back very far to appreciate how difficult it is to win an American Classic. He knows that no matter how fabulous your horse looks or trains that luck is involved – including the misfortunate of running into horses who are simply faster. Winchell’s best finish in the Kentucky Derby was a third in 2016 by Gun Runner. He would go on to win the $6 million Breeders’ Cup Classic (G1) in 2017, earning the Horse of the Year title. He capped his career with one race in 2018, taking Gulfstream Park’s $16 million Pegasus World Cup (G1) before heading off to stud duties at co-owner Three Chimneys Farm with earnings just shy of $16 million.

Gun Runner did not run in the Preakness and progressed from being a very good 3-year-old into a dominant champion at 4. Winchell is hoping Midnight Bourbon likewise will improve with age, though quicker the better, preferably Saturday.

Midnight Bourbon, winner of the Lecomte (G3) whose only finish worse than third in eight starts came in the Kentucky Derby, is the third choice in the Preakness morning line at 5-1 in a field of 10 3-year-olds. He will break from Post No. 5. With two-at-a-time loading, he’ll go into the gate next to last.

“If you had said, ‘Here’s 10 spots. Put all the horses where you want them to be,’ it would be pretty close to how it turned out. Which never seems to happen,” Winchell said.

In fact, it’s making him nervous how things so far have fallen into place.

“I’ve got people calling me, ‘I really like your horse,’” he said, adding with a laugh, “It’s like, ‘No. Stop it! Stop it!’”

Winchell has built upon the high-quality breeding and racing operation that his late father Verne started in the 1950s. With Ron taking over Winchell Thoroughbreds in partnership with his mother, Joan, upon Verne’s death in 2002, the Winchell Thoroughbreds stable has campaigned Gun Runner, 2014 Kentucky Oaks (G1) and Breeders’ Cup Distaff (G1) heroine Untapable, 2012 Breeders’ Cup Dirt Mile (G1) winner Tapizar, 2008 Louisiana Derby victor Pyro, 2005 Kentucky Oaks winner Summerly, and Cuvee, one of the top 2-year-olds of 2003, along with many other stakes winners.

The last horse Winchell purchased with his father was a silver-hued yearling bought two months before Verne’s death at age 87. That colt named Tapit captured the 2004 Wood Memorial (G1) to emerge among the favorites for the Kentucky Derby. Tapit finished ninth in the Derby, but his real fame has come as a breed-shaping stallion and one of the sport’s best sires of the last half-century.

“Winning the Derby has always been a focus,” Winchell said. “However, when my dad was around, we focused a little more on probably the speed element than the Derby distance. It’s kind of two different horses: the ones who are going to win as 2-year-olds at Saratoga and Del Mar. That’s a different set-up traditionally than the guy who is going to win the Derby.

“I’ve changed that focus to a certain degree in probably the last five to 10 years,” he added. “It’s reflective in the amount of starts we’ve had in the Derby.”

Verne Winchell had four Kentucky Derby starters, the best finish being Classic Go Go’s fourth in 1981. Midnight Bourbon became the eighth Derby runner for his son.

“We’re getting to the Derby; we’re just not performing in the Derby,” Winchell said. “However, Kentucky Oaks starters, we’ve started four with two winners. A little better record there. But it’s one of the categories that has been very elusive for our stable, winning Classic races. Breeders’ Cup races, yeah, we’ve won a number of those. We’ve brought some pretty good horses to the Derby. I think Gun Runner had a pretty good chance, but at that stage of his career, he couldn’t get to the finish line first. I mean, it is what it is.”

Midnight Bourbon will be Winchell’s third Preakness starter, following Tenfold’s close third in the fog to eventual Triple Crown champion Justify three years ago and Pneumatic’s 10th last year when the COVID-delayed race was in October. His dad finished fourth in the 1991 Preakness with Arkansas Derby (G1) winner Olympio.

Though he hasn’t had as many starters as in the Derby, Winchell said the Preakness is a race he very much covets, along with its iconic Woodlawn Vase, of which the winning owner gets a replica.

“It is one of those great races you grow up hearing about,” Winchell said. “I’d love to win. I’d love to get it behind me, honestly, because we’ve performed well in all sorts of races. There’s probably not a lot that we haven’t won over the course of my involvement in racing and my dad’s. These are ones that have eluded us. It’s a super cool race to win. The trophy is one of the best. I’ve love to have a spot for it on the mantel somewhere.”

Midnight Bourbon schooled at the starting gate, followed by a routine gallop, Thursday at Pimlico. He was scheduled to school in the paddock during the races.

Asmussen is pursuing a third Preakness victory, having won his first Triple Crown race in 2007 with two-time Horse of the Year Curlin and then two years later with the filly and 2009 Horse of the Year Rachel Alexandra.

“It is the Preakness and a great opportunity, being an American Classic and having a quality horse like this for Winchell Thoroughbreds,” Asmussen said. “If you’ve ever seen him, you realize the potential that’s there.”

Asmussen’s parents, Keith and Marilyn, raised and prepared all of Verne Winchell’s young horses for the races at their Laredo, Texas, training facility. That decades-long association has continued into the next generation, strengthened even more by Steve Asmussen being Ron’s primary trainer.

“I’m extremely proud of the Winchell and Asmussen connection,” Asmussen said. “Ron’s father and my father did business and had a lot of success before they let me or Ron make any decisions. So it’s extremely exciting for us.”