Tales from the Crib: Sierra Leone

Apr 08, 2024

Sierra Leone before selling for $2.3 million as a yearling (Photo courtesy of ThoroStride)

John and Debby Oxley have savored the experience of winning the Kentucky Derby (G1) as owners, when Monarchos stormed to victory in the 2001 edition at Churchill Downs. Now they could celebrate a Derby win on the breeding side of the equation, if Sierra Leone – bred in Debby’s name, and born at the Oxleys’ Fawn Leap Farm – prevails in the 150th Run for the Roses.

Trainer Chad Brown aptly summed up Sierra Leone in his postrace interview at Keeneland, moments after the exciting colt enhanced his Derby credentials in the Blue Grass (G1):

“He’s been a star since he’s been born.”

You could surmise that, since Sierra Leone sold for $2.3 million as a yearling, the top price at the boutique Fasig-Tipton Saratoga Sale. His owners are among the shrewdest operators in the industry, an international partnership including the Coolmore principals and Peter M. Brant.

Yet the show-stopping combination of pedigree and physique only gets a youngster so far. There’s an awfully long road to travel from the auction ring to the racetrack, let alone the Derby trail, and Sierra Leone has continued to excel throughout his life.

As an added twist to his tale, one of Sierra Leone’s Derby rivals – Japan’s unbeaten Forever Young –descends from the exact same family nurtured by Debby. The two are “cousins,” produced by half-sisters. While Forever Young’s mother, Forever Darling, was sold, Sierra Leone’s mother, Heavenly Love, remained in the Oxley fold.

Their rise to prominence is especially heartwarming, considering how Debby came to cultivate the female line in the first place. The story is recounted by Eric Mitchell in the April edition of Blood-Horse.

Debby loved watching Roamin Rachel, who captured such major races as the Ballerina H. (G1) at Saratoga, the Beaumont (G2) at Keeneland, and the Brown & Williamson H. (G3) at Churchill (now known as the Grade 1 Derby City Distaff). Debby was enamored of Roamin Rachel’s classy consistency, as evidenced by her record of winning or placing in 14 of 15 career starts.

“I was a big fan of Roamin Rachel,” Debby told Mitchell. “She was a hard-knocking filly who always gave everything.”

When a yearling filly out of Roamin Rachel was offered at Keeneland September in 1998, John purchased her for Debby. The $300,000 anniversary gift would be named, fittingly enough, Darling My Darling. Little could they have foreseen her long-term impact.

Darling My Darling missed narrowly in two prestigious events as a juvenile, the 1999 Frizette (G1) (to future champion Surfside) and Matron (G1). She later went on to land the Raven Run S. and Doubledogdare S., both at Keeneland. Two of her daughters would earn graded laurels, and two others would become graded stakes producers themselves.

Forever Darling (by Congrats), let go for a mere $8,000 as a yearling, was a gritty winner of the 2016 Santa Ynez (G2). That caught the attention of Northern Farm impresario Katsumi Yoshida, who struck a deal to acquire her privately. Although she didn’t achieve anything else of note stateside, Forever Darling turned out to be a valuable addition for Northern Farm; she’s now responsible for arguably the best-ever Japanese candidate for the Kentucky Derby in Forever Young.

Darling My Darling has exerted an influence even through unraced daughters. Sky My Darling (by the Oxleys’ own Sky Mesa) was exported to Brazil, where she foaled multiple Group 3 scorer Charles Do Bronxs. Darling’s Darling (by champion Bernardini) stayed home to produce Grade 3-placed On Alert as well as current Triple Crown nominee Northern Flame (by the Oxleys’ Flameaway), who was third in the Feb. 24 Rebel (G2).

It’s apropos that Darling My Darling’s top performer, Heavenly Love, is basking in the limelight as a producer herself. Like her aforementioned half-sisters, who are all by A.P. Indy-line stallions, Heavenly Love is by A.P. Indy’s son Malibu Moon. She emulated her mother’s, and grandmother’s, affinity for Keeneland by scoring her signature win in the 2017 Alcibiades (G1).

Unplaced in that fall’s Breeders’ Cup Juvenile Fillies (G1) at Del Mar, Heavenly Love would eventually visit the brightest star of that Breeders’ Cup, Classic (G1) hero and Horse of the Year Gun Runner, in their new careers at stud.

The resulting offspring, a dark bay colt, was born on March 31, 2021 at the Oxleys’ Fawn Leap near Midway, Kentucky.

“I remember Sierra Leone as a foal,” Fawn Leap manager Laurie Gimmon said in a video for Blood-Horse Plus. “She (Heavenly Love) can get a little hot, and get a little antsy, but he was very even-keel, very smart.

“He was so level-headed, and such a good boy. Everything that’s been asked of him, he’s done, and it’s just so gratifying to see that.”

The good boy grew into a grand stamp of a yearling. Set to be consigned on the Oxleys’ behalf by Gainesway Farm, the colt drew rave reviews from their team as well, as you can see from the promotional video.

“When I first saw him in the spring, an alarm kind of went off in my head,” Gainesway’s general manager, Brian Graves, said in the build-up to the sale. “This is one of the best horses I’ve seen this year.

“What I like about this colt is his size and scope. He’s got a beautiful long neck with a deep girth, highly intelligent, and has a lot of class. One of the best-moving horses on the farm….”

That assessment was echoed by Gainesway’s farm manager, Sherri Ivanovich, who described his motion as a “really floating, flowing type of walk.”

Gainesway’s yearling manager, Lester Rogers, forecast a bright future: “I think that he’ll do himself and his sire proud once he starts racing.”

The Gun Runner-Heavenly Love colt was indeed a standout at the sale, catching the eye of onlookers. Zoe Cadman, in a recent Thoroughbred Daily News podcast, recalled him as the best yearling she’d ever seen.

No wonder he set off fireworks in the ring at Saratoga, with Brant’s White Birch Farm and Coolmore’s M.V. Magnier joining forces to secure him for the sales-topping $2.3 million.

For his early lessons in racecraft, Sierra Leone was sent to David Scanlon, whose lengthy list of graduates includes some very memorable names. Initially working alongside his late father, Robert, who passed away in 2005, David has taught the likes of Unbridled’s Song, dual classic champion Afleet Alex, 2004 Kentucky Derby runner-up Lion Heart, Bernardini, and 2007 Belmont (G1)-winning champion filly Rags to Riches. In recent years at his Williston, Florida, operation, he’s developed undefeated Grade 1 star Army Mule and $2.2 million-earner By My Standards, both sold under the Scanlon banner at two-year-olds in training sales.

Interestingly, Scanlon’s memories of Sierra Leone mirror the descriptions from those who were around him in his baby and yearling days.

The colt had a “beautiful body, beautiful frame,” but what stood out for Scanlon was that he was a “really good walker – he had that catlike, nice, big, loose walk.” Still as “level-headed” as ever, he was a good student throughout the breaking and training process.

Around December of his yearling year into January, when he officially turned two, Sierra Leone had another growth spurt, and got very leggy and tall at that stage.

“He was never really awkward” in his training, Scanlon reported. “He just needed time to fill in,” so that his body could catch up proportionally to his height.

Sierra Leone at Scanlon Training & Sales in Florida (Photo courtesy of David Scanlon)

By the end of February and beginning of March 2023, Sierra Leone was ready to be asked for a little more speed in his works. Another pricey Coolmore purchase by Gun Runner from the same Saratoga Sale, the $1.4 million colt who would be named Hall of Fame, was in the same group at “school,” making for a point of comparison.

Hall of Fame was “more precocious and aggressive in his training,” Scanlon observed, while Sierra Leone’s works were also good, but in a more laid-back fashion. A very good-minded colt, Sierra Leone was advertising himself as the type to come to hand at three.

Advancing to Brown’s barn at Belmont Park last summer, Sierra Leone recorded his first three-furlong breeze Aug. 20 in a leisurely :38.92 over the training track. He gradually ratcheted up from there, and his sharp half-mile moves in the latter part of October showed that it was time for his first start.

Sierra Leone debuted going a mile at Aqueduct on Nov. 4, the day after Fierceness stamped himself as the divisional champion in the Breeders’ Cup Juvenile (G1). As would become his custom, Sierra Leone kicked into overdrive late to win going away by 1 1/4 lengths.

Stretching out to 1 1/8 miles in the Remsen (G2) at Aqueduct figured to be the right idea, but the promising colt dropped much farther back to last, as many as a dozen lengths behind front-running Dornoch. Nevertheless, Sierra Leone uncorked a monster move, defying the track bias against deep closers, to collar Dornoch. Just when it appeared as though he had the trophy in his grasp, though, the inexperienced Sierra Leone let the savvier Dornoch come back to beat him by a nose.

Brown added blinkers to encourage Sierra Leone to get a little better position, and not be quite so laid-back early, in the Risen Star (G2). Ironically, he renewed acquaintance with his classmate Hall of Fame, who had just broken his maiden in a spectacular romp for Steve Asmussen. Hall of Fame didn’t follow up in the same vein on the Derby trail, but watch out for him to progress in the future.

Sierra Leone was still unhurried off the Risen Star pace with new rider Tyler Gaffalione, but within a readier striking range. Timing his move just right, Sierra Leone mowed down longtime leader Track Phantom in what’s proven to be the key prep. Risen Star third-placer Catching Freedom came back to win the Louisiana Derby (G2), and fourth Resilience rolled in the Wood Memorial (G2).

The point was reiterated by Sierra Leone in the Blue Grass, upholding the family tradition to win at Keeneland. Another powerful late rush propelled Sierra Leone past Just a Touch, a fellow highly-regarded Scanlon alum. Back in fourth was old foe Dornoch.

Just a Touch had come through Scanlon’s sales curriculum, bought for $125,000 as a “pinhook” venture to resell as a two-year-old. He did attract $300,000 at OBS April, but Scanlon felt as though he’d fallen through the cracks a bit at the sale, where he might well have sold for more.

Scanlon saw something special in Just a Touch, who’s validated that belief by earning his way into the Derby in a short span of time for trainer Brad Cox. The son of Triple Crown champion Justify is eligible to keep improving ahead of his rematch with Sierra Leone in the Derby. It would be quite a coup if Scanlon graduates are fighting out the finish on the first Saturday in May.

By the same token, it’s amazing for the Oxleys that two grandsons of their beloved Darling My Darling, Sierra Leone and Forever Young, rank among the very leading contenders for Derby 150. The 27-year-old mare is enjoying her twilight years as the queen of Fawn Leap, and her reign just might extend to Churchill Downs.

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