Skippylongstocking's Preakness Bid Could Be Monumental For Doble Jak Investments, Top Line Sales - Horse Racing News | Paulick Report

Skippylongstocking’s Preakness Bid Could Be Monumental For Doble Jak Investments, Top Line Sales

Skippylongstocking at Pimlico

For many in this year's Preakness Stakes field, the road to Pimlico Race Course involved a six-figure trip through the auction ring. Skippylongstocking took a similar route to Baltimore, but with a key detour.

The Exaggerator colt is the lone horse in the Preakness field to change hands at a 2-year-old sale prior to his racing career, and his $37,000 sale price at the 2021 Ocala Breeders' Sales Co. Spring Sale of 2-Year-Olds in Training was the lowest of this year's entries.

Across town from Pimlico, Jimbo Gladwell plans to watch the race from the Maryland State Fairgrounds as he shows horses from his Top Line Sales consignment ahead of the Fasig-Tipton Midlantic 2-Year-Olds in Training Sale. If Skippylongstocking pulls off the upset, it would be a monumental name to add to Top Line's fast-growing list of prominent alumni.

However, Gladwell is quick to acknowledge that he did not have his hands on the horse for very long before he went through the ring. The colt shipped directly to the Top Line shedrow at last year's OBS Spring sale after the father-son team of Tito and Luis Guevara of Doble Jak Investments did the heavy lifting getting him ready.

“They did a great job with the horse,” Gladwell said. “They had the horse ready. He came straight to us and trained good, prepped good, was in one piece, and we just got the honor of selling him for them. We didn't do a whole lot of work other than hold him together and point him down the track.”

Getting a horse in the gate for any of the Triple Crown races is a triumph against the odds for even the biggest operations that start and resell racehorses, but Skippylongstocking's entry in the Preakness is a special kind of moonshot for the Doble Jak operation, which keeps its numbers between five and 10 young horses to start each year.

“It's pretty much me, my father, and my grooms,” Luis Guevara said about the Florida-based Doble Jak operation. “For the most part, we like to keep it small and hands-on.”

Luis (left) and Tito Guevara of Doble Jak Investments.

Luis said he and and his father Tito complement each other's strong points when it comes to pinhooking horses.

Luis handles the business end, taking care of the buying and selling of the horses, working with the consignors, sale companies, clients, and potential buyers. Tito, who was a jockey in Venezuela for over 25 years, handles what can be done in the saddle.

“He's the mastermind,” Luis said of his father. “I've learned not to question him. He always seems to be right.

“The best sale horse we ever had was Sarah Sis,” he continued. “We breezed her, I'm not lying to you, one time, and he said, 'We're not breezing this filly again until we get to OBS.' We never breezed her again. She ended up earning almost a million dollars at the races. After that, I thought maybe I should listen to him a little more.”

Both Luis and Tito were skeptical of Skippylongstocking before he went through the ring at the 2020 Keeneland September Yearling Sale, but the colt fit their price range between $10,000 and $20,000, and as the very last horse on offer for the session, they wondered if they might find a soft spot in the market after most other buyers had left for the night.

“The sale was really hard that year, everything was so expensive,” Luis said. “He comes up, and I kind of overlooked him because he was really immature. He was a big horse, lanky and narrow, but you could tell he was going to need a lot of time.

“I remember the guy running the (consignor) South Point shows saw me looking at him, and my dad and I were walking away, and he comes up running and says, 'Man, you need to take another look at him. His half-brother is breezing pretty hard at Gulfstream,'” Luis continued, referencing Moonlite Strike, who has since become a stakes winner. “We went back I talked to my dad, and he said if we give him the time, he thought he was going to be a nice horse. He was so lanky, and we knew if we put in the time, he would fill out eventually, and that's pretty much how it went.”

Doble Jak landed the colt for $15,000. The underbidder was trainer Saffie Joseph Jr., who had Moonlite Strike in his barn. Joseph would eventually saddle Skippylongstocking, as well.

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Luis said the colt was never outstanding during his time learning how to become a racehorse with Doble Jak, but he wasn't a problem child in training. His behavior in the barn was another issue.

“He was pretty much straightforward,” Luis said. “The only thing that was different was his attitude. He was a very mean horse. Feeding time was bad for him, for us, because he used to try to kick you, bite you, run up to you. Stuff like that.”

The Doble Jak method for training is just that – methodical. Luis said his dad is patient to a fault when it comes to bringing a horse along, making sure the one or two furlongs they cover during the breeze show isn't the peak of their athletic careers.

“He doesn't like to push,” Luis said. “I get frustrated sometimes when I feel like we need to push them a little harder, but he gets on them, and he knows which ones are ready and which ones need a little more work. We only work them about five times prior to the sale.”

A young Skippylongstocking.

Skippylongstocking breezed an eighth of a mile in :10 2/5 seconds during the OBS Spring breeze show, and he finished under his reserve when he went through the ring. However, the Guevara team got the colt sold privately when he returned to the barn, going to owner Daniel Alsono – and into Joseph's barn – for $37,000.

Even if Skippylongstocking doesn't run a step on Satruday, it has already been a solid purchase for Alsono. Skippylongstocking has won a pair of races at Gulfstream Park and earned $156,100 on the racetrack, most recently finishing third in the Grade 2 Wood Memorial.

With a day left before the big race, Luis said he was still mulling over if and how he'd make it to the Preakness to watch Skippylongstocking run. It could be a once-in-a-lifetime opportunity, but he's also got to try to create the next once-in-a-lifetime opportunity.

“I was trying to get the tickets, but I'm not sure if I'm going to be able to make it to the race or not,” he said. “I've got four horses in the (OBS) June sale, and it kind of conflicts with the timing. I might not have one in there for a very long time, if ever again.”

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