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The first decade of the 2000s was highlighted by a number of top-class horses and memorable Triple Crown and Breeders’ Cup races. Here is the story of three of the decade’s biggest stars and the impact they have left.

CURLIN (HILL ‘N’ DALE AT XALAPA) AND STREET SENSE (DARLEY AT JONABELL)

Turning for home in the 2007 Preakness, racing fans all over the country were already envisioning the end of a 29-year Triple Crown drought. That is where Kentucky Derby winner Street Sense, who had dominated the Run for the Roses, blew by Curlin and closed in on Derby runner-up Hard Spun, who he had handled with no problem at Churchill Downs. With the Derby second- and third-place finishers seemingly out of the way there was no stopping Street Sense.

Members of the Street Sense camp standing by the rail were certain of victory. Hotwalker Paul Rutherford, exercise rider Mark Cutler, and groom Jose Herrarte all began pumping their fists in the air and jumping up and down in celebration. For the fans it was time to start booking their flight to New York to witness history being made in the Belmont Stakes. If they couldn’t beat Street Sense in the first two legs of the Triple Crown, how could they beat him going a mile and a half with his stamina-oriented pedigree?

Street Sense had already made history when he became the first 2-year-old champion since Spectacular Bid to win the Derby and the first Breeders’ Cup Juvenile winner ever to take home the roses.

With Street Sense having won the Derby with such authority, being trained by two-time Derby-winning trainer Carl Nafzger, and having a classic pedigree to run all day, what could possibly stand in his way? He was now a furlong away from being an overwhelming favorite to sweep the Triple Crown.

But suddenly the scene changed. Street Sense was not pulling away as he had done at Churchill Downs. Someone was bearing down on him. Much to the shock of everyone, it was Curlin, who surely looked like a beaten horse when Street Sense came up on his inside and surged past him at the head of the stretch.

Now it was a battle. Curlin, despite having only four career starts, was relentless. Street Sense dug in and kept fighting trying to hold off this unexpected opponent. But at the wire it was Curlin by a head, as the crowd went silent. Not only did Street Sense’s attempt at a Triple Crown sweep go up in the proverbial puff of smoke, the Triple Crown had turned into a mess, especially when a surprised and dejected Nafzger announced after the race that Street Sense would not run in the Belmont Stakes, depriving fans of at least a rubber match between the Derby and Preakness winner.

So, who exactly was this horse who stood in the way of history and totally disrupted what was to be a historic Triple Crown?

Let’s go back to beginning when Kenny McPeek picked out Curlin as a yearling at the Keeneland September sale for $57,000. The son of Smart Strike had an OCD lesion removed from his left ankle as a weanling, and it wasn’t a pretty sight at the sale. Although it turned off most buyers, McPeek felt it would be a non-issue. But his clients, Shirley Cunningham and Bill Gallion, became furious with McPeek for spending$57,000 on a horse with physical issues that no one wanted, especially after they were told he would never make it to the races. McPeek tried to assure them the colt would be fine, but got nowhere and offered to take the colt back and find another client. He felt he was a steal at that price and believed he would have gone for $300,000 if his ankle didn’t look so unappealing. Eventually, Cunningham and Gallion began to have second thoughts and decided to keep him.

McPeek at the time had actually given up training for a while to concentrate on bloodstock work, mainly in the U.S. and South America. Also, his mother was terminally ill. He contacted his owners and convinced them to keep the horses with his longtime assistant Helen Pitts and that he would always be close by.

Pitts was an excellent horsewoman and appeared to be a new major force in training, having immediate success with the help of assistant Hanne Jorgensen, who had exercised and taken care of Sarava for McPeek every day at Belmont Park prior to his shocking victory in the 2002 Belmont Stakes at odds of 70-1. When Pitts went out on her own, Jorgensen, who had become a good friend, went with her.

After spending several years focusing on bloodstock work, McPeek decided he wanted to get back to training and politicked to get Curlin, but Cunningham and Gallion had already promised him to Pitts and didn’t want to renege on their word.

Curlin was sent to Gail Garrison, manager of Cunningham’s Hillcrest Farm near Lexington, and he immediately began working on the colt’s physical problems. Curlin was at the farm for 60 days, where he was turned out in a paddock and allowed to eat grass each day. Garrison could see he was still a “big, playful kid who was full of vinegar.” He just needed time to grow up and settle into that big effortless stride of his.

Finally, he was sent to Pitts, and it didn’t take long for her and Jorgensen to start seeing those visions of greatness. When Jorgensen worked him, she came back and told Pitts, “I’ve never sat on a horse like this before.”

On July 29, 2006, the Southern Legislative Conference convened at Churchill Downs, where the legislators were treated to a night at the races, which included three exhibition races. When Churchill Downs’ senior vice president of racing, Donnie Richardson, asked Pitts to help out and put a couple of her 2-year-olds in the races, she chose Curlin, who wound up finishing third behind the Bernie Flint-trained Speedway, who had already broken his maiden by three lengths, but was still green and needed more experience.

Riding Curlin that night was Hanne Jorgensen’s husband, Mick Jenner. They had been going together for several years when they faced each other as competitors in the 2002 Belmont Stakes. Jenner was the regular exercise rider for Kentucky Derby and Preakness winner War Emblem. But it was Jorgensen who got the better of that battle, winning the Belmont with the little-regarded Sarava.

Jenner recalled his ride aboard Curlin that night at Churchill Downs. “Curlin had worked a couple of half-miles, but he was just a big ol’ 2-year-old who had never been asked to do anything at that point,” he said. “Everything he’d done was on the bit. The race was only a quarter of a mile and he was bucking and rearing, and I was hanging on for dear life. So I not only got Curlin beat, I got him well beat.”

As Curlin matured he began to convince Pitts and Jorgensen that he could be something special. They were expecting big things first time out, as, apparently, was everyone else, with Curlin going off as the 2-1 favorite. For a new trainer like Pitts, it’s a very fine line between joy and dread when a young 3-year-old runs off the screen in his debut, as Curlin did, winning by almost 13 lengths in a swift 1:22 1/5 for the seven furlongs. The crashing sound you usually hear afterwards is that of the rich folks breaking open their piggy banks. You know the million-dollar offers are going to start pouring in for that brilliant ready-made Derby horse, and that a sale is most likely going to result in the horse being given to the buyer’s trainer, especially if he’s Pletcher or Asmussen or Mott or Baffert.

So, when Curlin rocked the Derby trail in his debut, Pitts knew there was a good chance she could lose the horse. Ironically, at the time of Curlin’s victory, Steve Asmussen just happened to be stabled in her barn, preparing Leprechaun Racing’s Gunfight for the 6 1/2-furlong Swale Stakes, his only starter at the meet. Asmussen had recently lost his big Derby horse, Tiz Wonderful, owned by Jess Jackson’s Stonestreet Stables, to injury and had no idea how he was going to replace a horse of that caliber, one who was undefeated and had already won the Kentucky Jockey Club Stakes at Churchill Downs.

Because Asmussen was stabled in Pitts’ barn, he had gotten to see Curlin close up on a daily basis and was impressed with everything he saw. When Curlin romped in his debut, it set the wheels in motion. Watching the race on simulcast at the Ocala Breeders 2-year-old sale was John Moynihan, who was Jess Jackson’s bloodstock manager. Watching from his home in San Francisco was owner George Bolton. Both had the same reaction – “Wow!” Asmussen after seeing the race, watched the colt cool out and said to himself, “We’ve got to get that horse.”

Bolton contacted someone at the Ragozin Sheets and found out Curlin had run a “5 3/4,” an extraordinary number for a first-time starter. The pieces were beginning to come together.

Moynihan knew that the offers would start to pour in for the colt, so he drove down to Gulfstream to see the horse and then contacted Cunningham and Gallion. As he figured, an offer had already come in, this one from Barry Irwin, president of Team Valor, who offered $1.75 million, but, as Irwin put it, his bid was “blown out of the water” by subsequent bids. As it turned out, there were 15 bids on the horse, each with different stipulations.

Cunningham and Gallion wanted to stay in for a minority interest, and the day after the race, Super Bowl Sunday, Moynihan began negotiations, representing Jackson, Bolton, and another interested party, Satish Sanan. By 2 a.m. Monday morning, the deal was completed.

Although Cunningham and Gallion had received larger offers for the whole horse, the Moynihan group’s selling point was allowing them to stay in as minority partner. So they made a huge profit and were able to retain an interest in the horse they didn’t want and nearly gave back.

The only thing left to be done was for Moynihan to look at Curlin on the racetrack to see how he had come out of the race and to make sure he was sound. So, Pitts brought him to the track that morning and when Curlin began bucking and squealing, the deal was finalized for a reported $3.5 million. That would be the last time Pitts would lead him to the track.

Asmussen was delighted, having found his Derby horse. He felt everything was meant to be, because if Tiz Wonderful hadn’t gotten hurt, Jackson would not have been looking for a Derby horse to replace him, and, as he put it, he’d be trying to figure out how to beat Curlin instead of training him.

Pitts and Jorgensen were devastated, especially having to watch their dream horse depart after devoting so much time and effort getting him through some physical issues and becoming so close to him.

“I cried my eyes out when they sold him,” Jorgensen said shortly after the sale. “We babied him for such a long time. He bucked his shins twice and we tried to get him through it and worked hard with him. And then, one big race and he’s gone. We felt he was something special before he even started, we really did. I understand it’s hard to turn down that kind of money, and they did keep a piece of him, so it wasn’t hard for them. But it’s hard for us, because you get so attached to them.”

Curlin, of course, set off on his meteoric rise to stardom, winning the Rebel Stakes by 5 1/4 lengths and the Arkansas Derby by 10 1/2 lengths before finishing a well-beaten third in the Kentucky Derby after encountering traffic problems at a key point in the race. It was a terrific effort considering it was only the fourth start of his life, and the last horse to win the Derby with only three starts was Regret in 1915.

After his Preakness victory, Curlin would go on to a Hall of Fame career, winning the Breeders’ Cup Classic, Dubai World Cup, Jockey Club Gold Cup twice, Woodward Stakes, and Stephen Foster Handicap.

Street Sense returned from his brief vacation to win the Jim Dandy and Travers Stakes, but was soundly beaten by Curlin over a sloppy track in a showdown for Horse of the Year honors in the Breeders’ Cup Classic at Monmouth Park. He was retired to Darley at Jonabell Farm following the Classic joining Hard Spun, giving the farm the one-two finishers of the 2007 Kentucky Derby. Among Street Sense’s most notable stakes winners are Whitney, Malibu, and Pennsylvania Derby winner McKinzie and Maxfield, who is a leading contender for this year’s Breeders’ Cup Classic.

Curlin was retired to Hill ‘n’ Dale Farm with record earnings of $10.1 million dollars. He joined Secretariat, Forego, Affirmed and Cigar as the only horses to win consecutive Horse of the Year Eclipse Awards. He went on to sire a number of major stakes winners, including several classic and Breeders’ Cup winners, as well as Keen Ice, who upset Triple Crown winner American Pharoah in the Travers Stakes. In 2019, his son Vino Rosso emulated his sire by winning the Breeders’ Cup Classic. Curlin has also become one of the hottest stallions at the sales with a number of his offspring selling in the millions.

Kenny McPeek has trained a number of top-class horses over his career, many of whom he picked out himself. But he will always be known as the person who found and purchased Curlin for a meager $57,000, seeing well beyond his physical problems and having to defend his purchase to his irate owners.

“I was still around Curilin a great deal during the winter of his 2-year-old year in Ocala,” McPeek recalled. “He was a man among boys even then. I’m very proud to have found him and it was great visiting him at the farm several years ago. I have mixed emotions because any normal year I would have trained him, but my mother was terminally ill and the time away and how the events unfolded kept me from handling him. I’m motivated every time I go to an auction to find horses like him. I set the bar very high with him, but I love the challenge of it all.”

McPeek said that if he hadn’t stepped away from training and gone into bloodstock work he probably would not have been able to buy a historic 115-acre farm outside Lexington, Kentucky (renaming it Magdalana Farm) that dates back to the Revolutionary War and was home to such top horses as Kentucky Derby winner Tomy Lee and three-time Horse of the Year Devil Diver.

“Everything happens for a reason,” McPeek said.

He can only hope that one day the farm will produce another Curlin. But for now he will have to be content with picking out one of greatest horses of the century.

MEDAGLIA D’ORO (DARLEY AT JONABELL)

Medaglia d’Oro, like Curlin, is one of the most popular stallions at the sales and has sired numerous grade 1 winners, most notably Rachel Alexandra and Songbird, two of the greatest fillies of the modern era. Both stallions were amazing physical specimens who won or placed in the most prestigious stakes in America.

But that is where the similarities end. Although Curlin sold for dirt cheap as a yearling because of a physical issue, that was nothing compared to Medaglia d’Oro’s humble beginnings.

Despite his reign high atop the equine monarchy, Medaglia d’Oro, a son of El Prado, was not “to the manor born.” He in fact spent his youth on a farm in Montana and later did his early training literally in the middle of the Arizona desert.

Born at Katalpa Farm in Paris, Ky., Medaglia d’Oro was sent to the farm of his owner/breeders, Joyce and Albert Bell, who had a 110-acre spread outside Great Falls, Montana. After being broken, he was about to return to Kentucky for his early training when the Bells’ trainer, Kent Jensen, suggested they send him to a small ranch in Arizona, which was located pretty much in the middle of nowhere, between Cave Creek and Carefree, light years away from the Kentucky bluegrass

Running the ranch was Jensen’s exercise rider at Turf Paradise, Raland (Ral) Ayers, who worked there with his brother Lance. Jensen had helped them get started, lining up a few yearlings for them to break, and he and Ral would divide their time between the ranch and the racetrack. Lance also galloped horses for trainer Jeff Mullins, and broke eventual Santa Anita Derby winner Buddy Gil.

The Bells agreed to send Medaglia d’Oro to the Arizona ranch, shipping the big, strapping yearling down just after Thanksgiving. “The day he arrived, he had dapples on him you wouldn’t believe,” Jensen recalled.

Over the next five months, Medaglia d’Oro grew into a grand-looking racehorse, but it certainly wasn’t the conventional early training one would expect for a future star, who would win the Travers, Whitney, Oaklawn Handicap, Donn Handicap, Strub Stakes, Jim Dandy, and San Felipe Stakes and finish second twice in the Breeders’ Cup Classic, as well as the Belmont Stakes, Dubai World Cup, Wood Memorial, and Pacific Classic.

“It was just a little training track out in the middle of nowhere,” Jensen recalled. “It didn’t even have a rail. When I first saw the place I didn’t like it, but it was close enough to Turf Paradise. Ral would take Medaglia d’Oro out and go riding off through the desert, out there with the cactus.”

“I can’t even remember the name of the place,” Ayers said. “It was just a little cowboy ranch.”

But Ayers and Jensen certainly got more than they bargained for with Medaglia d’Oro. “He stood out right from the beginning,” Ayers recalled. “He had size and was well put together, and was very athletic. People would come to look at the young horses, and they’d always ask, ‘Who’s that one?'”

Jensen and Ayers began to think that maybe they had something special on their hands; certainly something you wouldn’t expect to find running out in the middle of the Arizona desert.

“The first day I had him out on the track for a jog, he bowed his neck and knew exactly what he was supposed to do,” Ayers said. “I had to back him up in order to slow him down. He was never intimidated by other horses. He was just a pro from day one. The first time I galloped him, he went between two horses like he’d been doing it all his life. I’ve never been around a horse with that much class.”

As Medaglia d’Oro’s training picked up, he continued to amaze Ayers and Jensen. “He’d go two miles with rings on, then breeze three furlongs in :35 1/5,” Jensen recalled. “You just didn’t see young horses breeze in :35 1/5 after going two miles. It was nothing to him. He had an unbelievable stride. I trained him like I would a 3-year-old. The first time Ral got on him, he told me, ‘This colt is something.’ I never train a 2-year-old two miles, but from the first day he stepped foot on the track he wanted to train. You live your life to be around a horse like this. He was something special.”

The following April, Medaglia d’Oro was ready to be shipped to the racetrack, and the Bells sent him to trainer Dave Vance. While training at Churchill Downs that fall, he caught the eye of former trainer-turned bloodstock agent Mark Reid, who had just bought a 2-year-old named Labamta Babe for Bobby Frankel and owner Edmund Gann. Reid wasn’t in the market for another young horse at the time, having just bought a potential classic prospect for Frankel.

Medaglia d’Oro made his first start on December 7 at Turfway Park and finished second, breaking from the 12 post. Shortly after the race, Vance packed up shop and headed for Oaklawn Park. In February, Reid showed up looking for a new Derby horse for Frankel after Labamta Babe suffered an injury following an impressive victory in the Santa Catalina Stakes.

When Reid ran into Vance at the rail one morning, he told him to keep an eye out for any good-looking 3-year-olds.

“Well, remember that colt you watched train at Churchill last fall?” Vance said. “There’s no horse on the grounds who can beat him. He was second first time out, and I’m gonna run him again pretty soon. Watch him and let me know what you think.”

When he was entered on February 9, Reid called Frankel and told him to watch this colt. With Reid watching from Philadelphia Park, Medaglia d’Oro won by 4 1/4 lengths in 1:10 4/5 for the six furlongs, earning a sensational 101 Beyer Speed Figure. Frankel was unable to get to a TV and missed the race, but Reid told him this was a horse they definitely wanted to pursue. Frankel saw the huge speed figures the colt posted and gave Reid the green light.

The Bells told Jensen about the offer, and he felt the price they were offering was too good to pass up. “If I had known he had run a 101 Beyer in that race, I would have told them not to sell,” Jensen said, “When they told me it was Frankel who had bought him, I said, ‘Well, at least we’ll find out how good he really is.'”

And that they did, as Medaglia d’Oro developed into one of the leading horses in the country, winning grade I stakes at 3, 4, and 5, while earning over $5.7 million.

Medaglia d’Oro became a sought after stallion prospect and following his retirement, he joined the elite band of Sheikh Mohammed’s stallions at Darley Stud and became the leading second-crop sire in North America. But that was only the beginning. His stock has continued to rise every year, especially when his daughter Rachel Alexandra shook up the racing world in 2009 at 3, defeating the boys in the Preakness and Haskell Invitational and then knocking off older horses in the Woodward Stakes.

At age 22, Medaglia d’Oro remains one of the country’s elite stallions. And it all began on a Montana farm nestled between the Rocky and Little Belt Mountains and a small ranch in the middle of the Arizona desert.