The path leading to the Kentucky Derby, sponsored by Woodford Reserve, proceeds through Oaklawn Park this Sunday, featuring the $1.25 million, Grade 2 Rebel Stakes. This race, covering 1 1/16 miles, consistently attracts a robust and highly contested group of participants, motivated by a substantial prize pool and 50 essential Derby qualification points awarded to the victor.
Initially launched in 1961 as the Rebel Handicap, the event transitioned to the Rebel Stakes in 1984. Concurrently in that year, its length was modified from one mile and 70 yards to 1 1/16 miles. In 1990, it achieved Grade 3 recognition, though it lacked a grade in 2003 and 2004, before advancing to Grade 2 status in 2008.
Over the past few years, the prize money for this competition has significantly escalated. In 2011, the event offered a $300,000 purse. By 2016, this amount had surged threefold to $900,000. It first featured a $1 million prize in 2020 and has maintained a seven-figure purse annually thereafter. Partly due to its generous prize fund, a roster of celebrated victors like Triple Crown champion American Pharoah, and its system for allocating 50-25-15-10-5 Derby qualifying points, the Rebel is assuredly a premier preparatory race for the Kentucky Derby each season.
We will now review some of the most distinguished champions of the Rebel Stakes.
TEMPERENCE HILL (1980)
CAREER RECORD: 31 starts, 11 victories, 4 runner-up finishes, 2 third-place showings
CAREER EARNINGS: $1,567,650
Temperence Hill commenced his racing journey without much promise at age two, failing to place in three races held in New York. For the start of his three-year-old campaign, he was relocated to Oaklawn Park, which served as the home turf for his proprietors, Loblolly Stable. Following two consecutive wins, he was entered into the Rebel Handicap for his initial stakes appearance.
Wagerers held low expectations for his prospects, giving him odds of 16.50-1. He trailed significantly in the initial stages, sitting 17 lengths behind the frontrunner after the first quarter-mile. Nevertheless, upon entering the final stretch, he accelerated dramatically, vigorously pursuing the leader, Be a Prospect. The latter offered no counter, and Temperence Hill effortlessly overtook him, extending his lead to a 2 ¼-length victory guided by jockey Darrell Haire.
In his subsequent two outings, Temperence Hill secured his inaugural graded stakes triumph, achieving a 1 ¼-length win in the Arkansas Derby. Yet, his omission from the Kentucky Derby nominations meant he could not participate. Following losses in two graded stakes competitions, Loblolly Stable and trainer Joseph Cantey opted to enter him in the Belmont Stakes. Temperence Hill was also not nominated for this event, necessitating a $5,000 supplementary charge in addition to the $15,000 entry cost. He was perceived as a considerable longshot at 53.40-1 odds, with Preakness victor Codex favored at 8-5.
Nonetheless, Temperence Hill achieved an unexpected victory. Guided by Eddie Maple, he outlasted Genuine Risk, the Kentucky Derby-winning filly, in the final stretch to claim a two-length win, yielding a substantial $108.80 payout for a victory bet. Demonstrating that his classic win was no mere chance, Temperence Hill subsequently triumphed in the Travers Stakes, the Jockey Club Gold Cup, and the Super Derby. By the close of the year, he was honored with the Eclipse Award as the premier three-year-old male.
SUNNY’S HALO (1983)
CAREER RECORD: 20 appearances, 9 victories, 3 runner-up placements, 2 third-place finishes
CAREER EARNINGS: $1,247,791
Sunny’s Halo, bred in Canada, showcased his most impressive performances in his native country in 1982, securing four stakes victories at his home track, Woodbine. These achievements garnered him the Sovereign Award for the top two-year-old male in Canada. His racing efforts in the United States, however, were less distinguished. In four American stakes attempts at age two, he only managed one top-three finish, securing third in the Tremont Stakes at Belmont Park. Consequently, he was not considered a strong Derby contender leading up to the 1983 season.
Sunny’s Halo commenced his three-year-old campaign no earlier than the Rebel on March 26. He started as the second favorite among the 11 competitors. Jockey Larry Snyder kept him positioned behind the frontrunners initially, then urged him forward around the bend. From that point, Sunny’s Halo pulled ahead to a decisive three-length win.
In his subsequent race, Sunny’s Halo triumphed in the Arkansas Derby by four lengths, guided by Eddie Delahoussaye. Despite these striking victories, uncertainties lingered regarding Sunny’s Halo ahead of the Derby. Historically, no horse had ever secured both the Arkansas Derby and the Kentucky Derby. Certain punters also worried about his limited preparation, having only two starts as a three-year-old before the Derby. Notwithstanding these reservations, Sunny’s Halo was the 5-2 second betting choice.
All skeptics were quieted following the race, as Sunny’s Halo executed an excellent stalking strategy and extended his lead to a two-length victory with Delahoussaye aboard. He achieved the distinction of being the first Canadian-foaled equine to win the Derby since Northern Dancer in 1964.
VANLANDINGHAM (1984)
CAREER RECORD: 19 races, 10 victories, 3 second-place finishes, 3 third-place finishes
CAREER EARNINGS: $1,409,476
Four years subsequent to Temperence Hill’s success, Loblolly Stable introduced another promising three-year-old. In his initial appearance at Oaklawn Park, preceding the Rebel, Vanlandingham decisively beat an allowance group by 10 lengths. Propelled by this dominant performance, he was established as the 6-5 favorite for the Rebel.
Vanlandingham fulfilled every anticipation during the Rebel. Despite needing to exert effort in the homestretch, Vanlandingham ultimately surged ahead in the concluding eighth of a mile to achieve a 1 ¼-length win with Pat Day riding. He completed the 1 1/16-mile distance in a remarkable 1:41.
He was withdrawn from the Arkansas Derby because of sickness but recuperated sufficiently to participate in the Kentucky Derby. Alongside his stablemate Pine Circle, he marked the initial Derby entrants for Loblolly Stables and their conditioner, Shug McGaughey. They were combined for betting purposes and assigned a robust 6-1 likelihood. Regrettably, Pine Circle secured a distant sixth position, whereas Vanlandingham suffered a fractured pastern bone mid-race, concluding in 16th place.
Although the ailment kept him sidelined for the remainder of his three-year-old campaign, Vanlandingham made a triumphant return at age four, performing with greater prowess than before. In his third race after the break, he clinched the Suburban Handicap by 8 ¾ lengths. Subsequently that year, he captured the Jockey Club Gold Cup by 2 ½ lengths, thereby becoming the inaugural multiple Grade 1 winner under McGaughey’s training. Despite a disappointing seventh in the Breeders’ Cup Classic, a victory on turf in the Washington D.C. International restored his standing and contributed to his Eclipse Award as champion older male.
PINE BLUFF (1992)
CAREER RECORD: 13 appearances, 6 victories, 1 second-place, 3 third-place finishes
CAREER EARNINGS: $2,255,884
Following an initial subdued phase in his career, Pine Bluff hit his peak performance by the conclusion of his two-year-old season. He concluded his 1991 racing year with triumphs in the Remsen and Nashua Stakes at Aqueduct.
For his three-year-old inaugural race, he secured a second-place finish in the Southwest Stakes, trailing the unexpected victor, Big Sur. Punters were undeterred by this loss, positioning him as the 3-10 favorite in his subsequent start, the Rebel Stakes. Guided by Jerry Bailey, Pine Bluff advanced to challenge the frontrunning Desert Force, pushing a swift pace. They completed the initial quarter-mile in 23.14 seconds, followed by a half-mile in 46.26 seconds. The two contenders sustained their rivalry into the homestretch, establishing a 10-length gap from the rest of the field.
During the final eighth of a mile, despite Desert Force’s persistent struggle, Pine Bluff gained the advantage and surged ahead in the late stages to claim a 2 ½-length victory, finishing the 1 1/16 miles in 1:42.83.
In his ultimate preparation for the Derby, Pine Bluff was the 4-5 favorite in the Arkansas Derby. He again engaged in a prolonged struggle, this time against Lil E. Tee, ultimately winning by a neck after an arduous stretch battle. For the Kentucky Derby, Pine Bluff was the third favored entry at 10.50-1 odds, with Craig Perret, his rider from his two-year-old season, resuming the reins. He concluded the race in fifth place, as Lil E. Tee reversed their previous outcome with an unexpected Derby triumph.
For the Preakness Stakes, Pine Bluff was assigned a different jockey, with Chris McCarron assuming riding responsibilities. He was the narrow 7-2 favorite among the complete field of 14 and performed as anticipated. Perret, aboard Alydeed, established a significant lead in the final eighth of a mile, but McCarron and Pine Bluff relentlessly pursued him, accelerating to secure a three-quarter-length victory. This marked Loblolly’s first Triple Crown race win since Temperence Hill’s success in the Belmont.
VICTORY GALLOP (1998)
CAREER RECORD: 17 outings, 9 triumphs, 5 runner-up spots, 1 third-place finish
CAREER EARNINGS: $3,505,895
At two years old, Victory Gallop claimed victory in two stakes races at Colonial Downs, executing powerful come-from-behind surges in both instances. He rounded off his juvenile season with an extraordinary second-place performance in the Laurel Futurity, where he advanced from second despite being disadvantaged by the pace and a wide racing path.
Subsequent to that notable race, Victory Gallop was acquired through a private transaction by Prestonwood Farm, who then entrusted him to the training of Elliott Walden. His initial start under these new affiliations occurred in the Rebel Stakes during late March. He was rated as the 4.10-1 third selection in a highly competitive betting event.
Rider Eibar Coa maintained his position relatively near the front as longshots Robinwould and Slew the Mark established a moderate tempo. As the contenders navigated the far turn, Coa urged his horse for acceleration in the third lane, and he advanced to challenge the leaders. He effortlessly passed Slew the Mark, but Robinwould resisted stubbornly on the inside, compelling a strenuous contest. Victory Gallop persevered to win by a head.
Subsequent to securing another hard-won triumph in the Arkansas Derby, Victory Gallop’s prospects for the Kentucky Derby were not highly favored. Priced at 14.60-1, he launched a strong rally from the very rear to claim second, defeated by a half-length by Real Quiet. As the favored contender in the Preakness Stakes, he again finished as the runner-up, but Real Quiet triumphed once more, positioning himself for a Triple Crown attempt in the Belmont Stakes.
That Belmont event stood out as one of the most exciting iterations in the history of the race. Kent Desormeaux guided Real Quiet to an early lead, and he distanced himself from the pack as the horses navigated the final bend, with five-sixteenths of a mile yet to be covered. Victory Gallop, ridden by Gary Stevens, remained far behind but began to accelerate rapidly as they straightened for the finish. In the homestretch, Real Quiet started to falter, while Victory Gallop surged down the track in his effort to prevent a historic win. Despite Real Quiet veering outwards into Victory Gallop’s lane in the stretch, Victory Gallop closed with immense force to seize victory, thereby stopping Real Quiet from achieving the Triple Crown.
While Victory Gallop was unable to claim the champion three-year-old male Eclipse from Real Quiet, he did secure year-end accolades at age four. In 1999, he earned two Grade 1 victories, notably triumphing in a thrilling stretch duel against Behrens in the Whitney Handicap, which led to his Eclipse Award as the premier older male.
SMARTY JONES (2004)
CAREER RECORD: 9 races, 8 victories, 1 second-place, 0 third-place finishes
CAREER EARNINGS: $7,613,155
To commemorate their 100th anniversary in 2004, Oaklawn Park chose to enhance its pathway to the Kentucky Derby. They declared that any horse winning the Rebel Stakes, the Arkansas Derby, and the Kentucky Derby consecutively would be awarded a $5 million bonus.
That proposition was highly appealing to Smarty Jones, a Pennsylvania-bred. He secured victories in his initial three races, competing at Philadelphia Park (presently known as Parx Racing) and Aqueduct, by a cumulative margin of 27 ¾ lengths. Despite his owner, Someday Farm, and trainer, John Servis, being located on the East Coast, they opted to dispatch their valuable colt to Oaklawn for Derby preparations.
During his debut at Oaklawn, Smarty Jones triumphed in the Southwest Stakes by three-quarters of a length. Even with his perfect record, he did not garner significant attention at the betting counters on Rebel Stakes day. He was ranked as the 7-2 third favorite, trailing the highly publicized Todd Pletcher-trained Purge and the Fair Grounds-shipped Mr. Jester.
Purge surged to the front, while Stewart Elliott kept Smarty Jones positioned closely behind the leader in second. As the group navigated the far bend, Purge sustained a slight lead, yet Smarty Jones persistently advanced. Purge offered no counter in the final eighth, and Smarty Jones powered clear to a 3 ¼-length win.
After a commanding victory in the Arkansas Derby, Smarty Jones headed to Louisville as the favorite for the Kentucky Derby, aiming to be the first undefeated Derby champion since Seattle Slew in 1977. On a muddy course, he gradually overcame the frontrunner Lion Heart to achieve a 2 ¾-length win, thereby securing the $5 million bonus.
Smarty Jones subsequently claimed the Preakness Stakes in a compelling manner, positioning himself to become the inaugural Triple Crown victor in 26 years. An audience exceeding 120,000 converged at Belmont Park for the Belmont Stakes to support the beloved Pennsylvania-bred. He was defeated by the late-charging, unexpected winner Birdstone in one of the century’s most unforgettable Triple Crown contests.
CURLIN (2007)
CAREER RECORD: 16 appearances, 11 victories, 2 second-place finishes, 2 third-place finishes
CAREER EARNINGS: $10,501,800
Curlin garnered national racing attention from the very moment of his initial outing. He triumphed in his debut at Gulfstream Park in February 2007 by 12 ¾ lengths, completing seven furlongs in 1:22.25. Following that victory, Stonestreet Stables acquired an 80% interest in the colt for $3.5 million, subsequently entrusting him to trainer Steve Asmussen.
In his second race, Curlin was immediately thrust into a challenging competition, becoming the second betting favorite in the Rebel Stakes. Facing a more formidable lineup and extending his distance around two turns for the first time, he performed with equal impressiveness. He executed a wide, four-path maneuver on the bend and surged ahead in the stretch to achieve a commanding 5 ¼-length victory. Immediately, Curlin emerged as a top contender for the Kentucky Derby.
In his ultimate preparatory race for the initial Saturday of May, Curlin secured the Arkansas Derby by 10 ¼ lengths. Despite not competing at two years old and having only three races to his credit, Curlin was the 5-1 second favorite for the Kentucky Derby. He placed third behind Street Sense, yet he retaliated for that loss with a victory in the Preakness Stakes. Curlin suffered defeat in an exhilarating Belmont Stakes against the filly Rags to Riches, but later that year, he triumphed in the Jockey Club Gold Cup and the Breeders’ Cup Classic, thereby securing the Horse of the Year distinction.
During his four-year-old season in 2008, Curlin augmented his accomplishments with an additional Horse of the Year award, achieving four Grade or Group 1 victories. He also became the inaugural American-based horse to exceed $10 million in total career winnings.
LOOKIN AT LUCKY (2010)
CAREER RECORD: 13 races, 9 victories, 1 second-place, 1 third-place finish
CAREER EARNINGS: $3,307,278
Lookin At Lucky earned the Eclipse Award as champion two-year-old male for 2009, propelled by four stakes triumphs. Had it not been for a narrow head defeat in the Breeders’ Cup Juvenile, his season would have been flawless. Nevertheless, he was considered a formidable Derby contender entering his three-year-old debut in the Rebel Stakes.
Notwithstanding his notable achievements, Lookin at Lucky was not the undisputed top choice. Dublin, coming off a runner-up performance in the Southwest Stakes, was the 7-5 second preference. Lookin At Lucky, conversely, ended up as the 11-10 favorite. During the race, Lookin At Lucky positioned himself off the pace, several strides from the rail, then shifted wide in the homestretch. At the eighth pole, he maintained third place, still two lengths adrift of the battling Dublin and Noble’s Promise. While Dublin weakened in the concluding sixteenth of a mile, Noble’s Promise held firmly to the lead. With persistent encouragement from Garrett Gomez, Lookin At Lucky overcame Noble’s Promise in the very last stride to clinch a photo finish victory. This triumph marked trainer Bob Baffert’s first of seven Rebel Stakes wins.
Following a third-place showing in the Santa Anita Derby and a sixth-place performance in the Kentucky Derby, Lookin at Lucky’s prominence waned somewhat. He rebounded in his subsequent race with a valiant three-quarter-length victory in the Preakness Stakes. He then amassed two additional graded stakes wins in 2010 and secured another Eclipse championship, this time as the premier three-year-old male.
WILL TAKE CHARGE (2013)
CAREER RECORD: 21 starts, 7 victories, 6 runner-up finishes, 1 third-place result
CAREER EARNINGS: $3,924,648
As he approached the 2013 Rebel Stakes, Will Take Charge presented an inconsistent profile. He commenced his three-year-old campaign with a triumph in the Smarty Jones Stakes and secured second place in the Remington Springboard Mile in his previous race. Nevertheless, the D. Wayne Lukas-trained horse entered the Rebel following a poor sixth-place finish in the Southwest Stakes, where he was defeated by 18 lengths by Super Ninety Nine. Will Take Charge was considered a 28-1 longshot for the Rebel, while Super Ninety Nine was backed heavily to 6-5 favoritism.
Will Take Charge occupied the sixth position early in the race, maintaining a distance of approximately three lengths behind the frontrunner, Title Contender. Rounding the final turn, Super Ninety Nine and Oxbow (Will Take Charge’s stable companion) distanced themselves from the other competitors, while Will Take Charge held third. Super Ninety Nine faltered in the concluding eighth of a mile, and Oxbow surged ahead. Propelled by Jon Court, Will Take Charge made a late charge at the leader and rallied to overcome Oxbow by a head, orchestrating an unexpected victory.
Following that triumph, Will Take Charge participated in all three Triple Crown events, achieving no higher than a seventh-place finish in any. Oxbow subsequently claimed the Preakness, with Will Take Charge trailing by 16 lengths, but Oxbow’s performance declined thereafter. In contrast, Will Take Charge gained significant momentum for “the Coach” near the season’s conclusion. He captured the Travers Stakes, the Pennsylvania Derby, and the Clark Handicap, in addition to securing a second-place finish by a nose in the Breeders’ Cup Classic, which led to his Eclipse Award.
AMERICAN PHAROAH (2015)
CAREER RECORD: 11 outings, 9 victories, 1 runner-up placement, 0 third-place results
CAREER EARNINGS: $8,650,300
Even though he did not compete in the Breeders’ Cup, the Bob Baffert-conditioned American Pharoah was designated champion two-year-old male for 2014, a recognition founded on his two Grade 1 wins in California. He staged his return in the Rebel Stakes, where he was established as the commanding 2-5 favorite among the seven-horse field.
American Pharoah swiftly overcame a poor start and immediately took the lead. Upon reaching the first quarter-mile, he held a 1 ½-length advantage and maintained a notably unhurried pace. None of his competitors harbored significant prospects of closing the gap, as he progressively widened his lead with each stride. On an exceedingly muddy course, he passed the finish line 6 ¼ lengths ahead of the rest, recording a time of 1:45.78.
The Rebel Stakes served as the springboard for an incredibly impressive season. That summer, American Pharoah achieved a clean sweep of the Triple Crown, marking the first horse to secure victories in the Kentucky Derby, the Preakness Stakes, and the Belmont Stakes since Affirmed in 1978. To cap off his accomplishments, he concluded his year with a commanding triumph in the Breeders’ Cup Classic. Through this win, he became the first horse since Unbridled in 1990 to win both the Kentucky Derby and the Breeders’ Cup Classic in the same calendar year.
