The Road to the Kentucky Derby Presented by Woodford Reserve winds its way through Oaklawn Park this Saturday, for the $1 million, Grade 2 Rebel Stakes. A competitive field is set to line up for this 1 1/16-mile event, with 50 qualifying Derby points going to the winner.

The race was inaugurated in 1961 as the Rebel Handicap, and was changed to the Rebel Stakes in 1984. That same year, the distance was adjusted from one mile and 70 yards to 1 1/16 miles. In 1990, the race was given Grade 3 status, but was ungraded in 2003 and 2004. It was upgraded to Grade 2 in 2008.

In recent years, this race has seen dramatic purse increases. In 2011, the race carried a purse of $300,000. By 2016, the purse had tripled to $900,000. It was held as a $1 million race for the first time in 2020. Thanks to its lofty purse, its list of high-profile winners including Triple Crown winner American Pharoah, and its 50-20-15-10-5 allocation of Derby qualifying points, the Rebel is guaranteed to be one of the season's major Kentucky Derby prep races.

Here, we’ll take a look back at some of the best winners of the Rebel Stakes.

TEMPERENCE HILL (1980)

CAREER RECORD: 31 starts, 11 wins, 4 seconds, 2 thirds

CAREER EARNINGS: $1,567,650

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Temperence Hill began his career inauspiciously as a 2-year-old, missing the board in three starts in New York. To begin his 3-year-old season, he was sent to Oaklawn Park, the home base of his owners, Loblolly Stable. Off two straight wins, he was sent to the Rebel Handicap for his stakes debut.

Bettors thought little of his chances, sending him off at 16.50-1. He was far behind early on, 17 lengths off the leader after the opening quarter-mile. However, as they turned for home he found another gear and charged hard after pacesetter Be a Prospect. That one had no response, and Temperence Hill cruised by him and drew off to a 2 ¼ length win under jockey Darrell Haire.

Two starts later, Temperence Hill won his first graded stakes with a 1 ¼-length win in the Arkansas Derby. However, he was not nominated for the Kentucky Derby so he was forced to sit that race out. After defeats in two graded stakes races, Lobolly Stable and trainer Joseph Cantey decided to take a shot in the Belmont Stakes. Temperence Hall was not nominated for that race either, so they had to pay a $5,000 supplemental fee on top of the $15,000 entry fee. He was considered a rank 53.40-1 outsider. Preakness winner Codex was the 8-5 favorite.

However, Temperence Hill pulled off a surprise. Under Eddie Maple, he wore down Kentucky Derby-winning filly Genuine Risk in the stretch to win by two lengths, paying a whopping $108.80 to win. Proving that he was no fluke classic winner, Temperence Hill won the Travers Stakes, the Jockey Club Gold Cup, and the Super Derby. At year’s end, he won the Eclipse Award for champion 3-year-old male.

SUNNY’S HALO (1983)

CAREER RECORD: 20 starts, 9 wins, 3 seconds, 2 thirds

CAREER EARNINGS: $1,247,791

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The Canadian-bred Sunny’s Halo did his best work in his home country in 1982, where at his home base of Woodbine he won four stakes races. Those wins earned him the Sovereign Award as the champion 2-year-old male in Canada. His American body of work, however, left something to be desired. In four stakes tries in the United States at age 2, he managed to finish in the top three just once, nabbing third in the Tremont Stakes at Belmont Park. As a result, he was not regarded as a serious Derby prospect going into the 1983 trail.

Sunny’s Halo did not make his 3-year-old debut until the March 26 Rebel. He went off as second choice in the field of 11. Jockey Larry Snyder rated him off the leaders early and then moved after them on the turn. From there, Sunny’s Halo drew off to a three-length victory.

Next out, Sunny’s Halo won the Arkansas Derby by four lengths under Eddie Delahoussaye. Despite the impressive wins, there were still some questions about Sunny’s Halo before the Derby. At that time no horse had won both the Arkansas Derby and the Kentucky Derby. Some bettors were also concerned about a lack of foundation, as he had only two starts as a 3-year-old before the Derby. Despite the doubts, Sunny’s Halo was the 5-2 second favorite.

The doubters were silenced after the race, as Sunny’s Halo got a great stalking trip and drew off to a two-length win under Delahoussaye. He became the first Canadian-bred horse to win the Derby since Northern Dancer in 1964.

VANLANDINGHAM (1984)

CAREER RECORD: 19 starts, 10 wins, 3 seconds, 3 thirds

CAREER EARNINGS: $1,409,476

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Four years after Temperence Hill, Loblolly Stable was back with another up-and-coming 3-year-old. In his Oaklawn Park debut the race before the Rebel, Vanlandingham impressively defeated an allowance field by 10 lengths. Off the strength of that win, he was made the 6-5 favorite in the Rebel.

Vanlandingham lived up to all expectations in the Rebel. Although he had to grind a bit in the stretch, Vanlandingham pulled clear in the last eighth for a 1 ¼-length victory with Pat Day in the irons. He covered the 1 1/16 miles in an impressive 1:41.

He was scratched from the Arkansas Derby due to illness but recovered in time to compete in the Kentucky Derby. Along with stablemate Pine Circle, he represented the first Derby starters for Loblolly Stables and their trainer, Shug McGaughey. They were coupled in the wagering, and given a strong 6-1 chance. Unfortunately, Pine Circle was a nonthreatening sixth, while Vanlandingham fractured a pastern bone during the race and finished 16th.

While the injury cost him the rest of his 3-year-old season, Vanlandingham returned better than ever at age 4. In his third start off the layoff, he won the Suburban Handicap by 8 ¾ lengths. Later that year, he won the Jockey Club Gold Cup by 2 ½ lengths, becoming the first multiple Grade 1 winner trained by McGaughey. Although he was a disappointing seventh in the Breeders’ Cup Classic, a win on grass in the Washington D.C. International restored his reputation and helped him win the Eclipse as champion older male.

PINE BLUFF (1992)

CAREER RECORD: 13 starts, 6 wins, 1 seconds, 3 thirds

CAREER EARNINGS: $2,255,884

After a bit of a slow start to his career, Pine Bluff found his best stride towards the end of his 2-year-old campaign. He capped off his 1991 season with wins in the Remsen and Nashua Stakes at Aqueduct.

In his 3-year-old debut, he was second in the Southwest Stakes behind upset winner Big Sur. Bettors were not deterred by that defeat and made him the 3-10 favorite in the Rebel Stakes next out. With Jerry Bailey in the saddle, Pine Bluff moved to engage pacesetting Desert Force and sent him through strong fractions. They went the opening quarter-mile in 23.14 seconds and followed it up with a half-mile in 46.26 seconds. The pair continued their duel into the stretch, opening up 10 lengths on the others.

In the last eighth of a mile, although Desert Force continued to fight, Pine Bluff got the upper hand and pulled clear late for a 2 ½-length win, completing the 1 1/16 miles in 1:42.83.

For his final Derby prep, Pine Bluff was the 4-5 favorite in the Arkansas Derby. He once again had to duel, this time with Lil E. Tee, but he prevailed in a long stretch battle to win by a neck. In the Kentucky Derby, Pine Bluff was the 10.50-1 third choice with Craig Perret, who rode him as a 2-year-old, getting back in the stirrups. He finished fifth as Lil E. Tee turned the tables with a Derby upset.

For the Preakness Stakes, Pine Bluff got another new jockey as Chris McCarron took over riding duties. He was the slim 7-2 favorite in the full field of 14 and lived up to expectations. Perret, riding Alydeed, opened up a clear lead in the last eighth, but McCarron and Pine Bluff chased him down, rallying for a three-quarter-length victory. It was the first Triple Crown race win for Loblolly since Temperence Hill’s Belmont.

VICTORY GALLOP (1998)

CAREER RECORD: 17 starts, 9 wins, 5 seconds, 1 thirds

CAREER EARNINGS: $3,505,895

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As a 2-year-old, Victory Gallop won two stakes races at Colonial Downs, making strong rallies from behind both times. He concluded his 2-year-old season with a monster second-place finish in the Laurel Futurity, where he closed from second despite being pace compromised with a wide trip.

After that big race, Victory Gallop was purchased privately by Prestonwood Farm, which transferred him to the care of Elliott Walden. He made his first start for the new connections in the Rebel Stakes in late March. He was the 4.10-1 third choice in a wide-open betting race.

Jockey Eibar Coa kept him fairly close to the pace as longshots Robinwould and Slew the Mark set moderate fractions. As the field rounded the far turn, Coa asked his mount for run in the three path and he moved to engage the leaders. He moved past Slew the Mark easily, but Robinwould dug in on the inside and would not let him by without a fight. Victory Gallop held on to win by a head.

Following another hard-fought win in the Arkansas Derby, Victory Gallop was not highly regarded going into the Kentucky Derby. At 14.60-1, he rallied from dead last to finish second, beaten half a length by Real Quiet. As the favorite in the Preakness Stakes, he once again closed for second, but Real Quiet prevailed again to set himself up for a Triple Crown bid in the Belmont Stakes.

That Belmont proved to be one of the most dramatic editions in the race’s history. Kent Desormeaux moved Real Quiet to the lead early on and drew off from the rest as the horses rounded the final turn, with five-sixteenths of a mile still to run. Victory Gallop, under Gary Stevens, remained well out of it, but began to hit top gear as they turned for home. In the stretch, Real Quiet began to tire while Victory Gallop flew down the stretch in his bid to thwart history. Even though Real Quiet lugged out in the stretch into Victory Gallop’s path, Victory Gallop closed powerfully to win, denying Real Quiet the Triple Crown.

Although Victory Gallop could not take the champion 3-year-old male Eclipse away from Real Quiet, he took home year-end honors at age 4. He won two Grade 1s in 1999, including a dramatic stretch battle in the Whitney Handicap over Behrens, to win the Eclipse as champion older male.

SMARTY JONES (2004)

CAREER RECORD: 9 starts, 8 wins, 1 second, 0 thirds

CAREER EARNINGS: $7,613,155

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For their 100^th anniversary in 2004, Oaklawn Park decided to spice up their road to the Kentucky Derby. They announced that if a horse swept the Rebel Stakes, the Arkansas Derby, and the Kentucky Derby they would win a $5 million bonus.

That offer proved very enticing for Pennsylvania-bred Smarty Jones. He won his first three starts, racing at Philadelphia Park (now known at Parx Racing) and Aqueduct, by a combined 27 ¾ lengths. Although his owner, Someday Farm, and trainer, John Servis, were East-Coast based they decided to send their prized colt to Oaklawn to prepare for a Derby run.

In his first Oaklawn start, Smarty Jones won the Southwest Stakes by three-quarters of a length. Despite his unblemished record, he did not command that much respect at the betting windows on Rebel Stakes day. He was the 7-2 third choice behind the much-hyped Todd Pletcher trainee Purge and Fair Grounds shipper Mr. Jester.

Purge went out to the lead, while Stewart Elliott rated Smarty Jones just off the leader’s flank in second. As the field rounded the far turn, Purge maintained a narrow advantage but Smarty Jones continued to edge closer. Purge had no response in the last eighth, and Smarty Jones pulled away for a 3 ¼-length victory.

Following a dominant win in the Arkansas Derby, Smarty Jones went to Louisville as the Kentucky Derby favorite, with a shot to become the first undefeated Derby winner since Seattle Slew in 1977. On a sloppy track, he wore down pacesetting Lion Heart for a 2 ¾-length victory, clinching the $5 million bonus.

Smarty Jones then won the Preakness Stakes in dominant fashion, setting himself up to become the first Triple Crown winner in 26 years. A crowd of more than 120,000 showed up to Belmont Park for the Belmont Stakes to cheer on the popular Pennsylvania-bred. He lost to late-running upset winner Birdstone in one of the most memorable Triple Crown races of this century.

CURLIN (2007)

CAREER RECORD: 16 starts, 11 wins, 2 seconds, 2 thirds

CAREER EARNINGS: $10,501,800

Curlin was on the national racing scene from the moment he made his debut. He won his first start at Gulfstream Park in February 2007 by 12 ¾ lengths, going seven furlongs in 1:22.25. After that win, Stonestreet Stables purchased an 80% share in the colt for $3.5 million and transferred him to trainer Steve Asmussen.

For his second start, Curlin was immediately sent into the deep end, and went off as the second betting choice in the Rebel Stakes. Against a tougher field and stretching out around two turns for the fist time, he was just as impressive. He made a big, four-wide sweep on the turn and powered away in stretch for a dominant 5 ¼-length win. Instantly, Curlin became one of the Kentucky Derby favorites.

In his final tune-up for the first Saturday in May, Curlin won the Arkansas Derby by 10 ¼ lengths. Despite not racing at age 2 and with only three starts under his belt, Curlin was the 5-1 second choice in the Kentucky Derby. He finished third behind Street Sense, but avenged that defeat with a win in the Preakness Stakes. Curlin lost a thrilling Belmont Stakes to the filly Rags to Riches, but later that year he won the Jockey Club Gold Cup and the Breeders’ Cup Classic to clinch the Horse of the Year title.

As a 4-year-old in 2008, Curlin added another Horse of the Year title to his résumé, notching four Grade or Group 1 wins. He also became the first American-based horse to pass $10 million in career earnings.

LOOKIN AT LUCKY (2010)

CAREER RECORD: 13 starts, 9 wins, 1 second, 1 third

CAREER EARNINGS: $3,307,278

Lookin At Lucky won the Eclipse for champion 2-year-old male for 2009 on the strength of four stakes wins. Were it not for a head defeat in the Breeders’ Cup Juvenile, he would have had a perfect season. Even so, he loomed as a serious Derby prospect going into his 3-year-old debut in the Rebel Stakes.

Despite his impressive résumé, Lookin at Lucky was not the overwhelming favorite. Dublin, off a second-place finish in the Southwest Stakes, was the 7-5 second choice. Lookin At Lucky, meanwhile, closed as the 11-10 favorite. In the race, Lookin At Lucky rated off the pace a few paths of the rail and then moved wide in the stretch. At the eighth pole he remained in third, still two lengths behind dueling Dublin and Noble’s Promise. While Dublin faded in the final sixteenth of a mile, Noble’s Promise remained strong on the lead. Under vigorous urging from Garrett Gomez, Lookin At Lucky wore down Noble’s Promise in the last stride to win in a photo finish. That win gave trainer Bob Baffert the first of his seven Rebel wins.

After a third-place finish in the Santa Anita Derby and a sixth-place effort in the Kentucky Derby, Lookin at Lucky’s star dimmed a bit. He bounced back in his next start with a game three-quarter-length Preakness Stakes win. He then tallied two more graded stakes wins in 2010 and earned another Eclipse championship, this time for top 3-year-old male.

WILL TAKE CHARGE (2013)

CAREER RECORD: 21 starts, 7 wins, 6 seconds, 1 third

CAREER EARNINGS: $3,924,648

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Entering the 2013 Rebel Stakes, Will Take Charge was a mixed bag. He began his 3-year-old season with a win in the Smarty Jones Stakes and was second in the Remington Springboard Mile in the race before. However, the D. Wayne Lukas trainee went into the Rebel off a dismal sixth-place finish in the Southwest Stakes, beaten 18 lengths by Super Ninety Nine. Will Take Charge was a 28-1 outsider going into the Rebel while Super Ninety Nine was bet down to 6-5 favoritism.

Will Take Charge was sixth in the early stages, racing about three lengths off pacesetting Title Contender. On the final turn, Super Ninety Nine and Oxbow (Will Take Charge’s stablemate) drew away from the rest of the field while Will Take Charge was third. Super Ninety Nine faded in the last eighth and Oxbow pulled clear. Under a drive from Jon Court, Will Take Charge surged at the leader late and rallied to defeat Oxbow by a head and pull off the upset.

After that win, Will Take Charge competed in all three Triple Crown races, finishing no better than seventh in any of them. Oxbow went on to win the Preakness and Will Take Charge finished 16 lengths behind, but Oxbow tailed off after that. Conversely, Will Take Charge caught fire for "the Coach" toward the end of the season. He won the Travers Stakes, the Pennsylvania Derby, and the Clark Handicap while also finishing second by a nose in the Breeders’ Cup Classic on his way to an Eclipse Award.

AMERICAN PHAROAH (2015)

CAREER RECORD: 11 starts, 9 wins, 1 second, 0 thirds

CAREER EARNINGS: $8,650,300

The great 'Pharoah' in 2015. (Eclipse Sportswire)

Despite not racing in the Breeders’ Cup, Bob Baffert-trained American Pharoah was voted champion 2-year-old male of 2014 based on two Grade 1 wins in California. He made his comeback in the Rebel Stakes, where he was made the overwhelming 2-5 favorite in the field of seven.

American Pharoah recovered quickly from a bad break and went immediately to the front. By the time he reached the opening quarter, he was 1 ½ lengths in front and setting very moderate fractions. None of his rivals had much hope of catching him and he opened up more and more with every stride. On a very sloppy track, he crossed the finish line 6 ¼ lengths clear of the others, stopping the clock in 1:45.78.

The Rebel proved to be a launching pad for an awe-inspiring campaign. That summer, American Pharoah swept his way through the Triple Crown, becoming the first horse to win the Kentucky Derby, the Preakness Stakes, and the Belmont Stakes since Affirmed in 1978. As the cherry on top, he completed his year with a dominant Breeders’ Cup Classic win. With that victory, he became the first horse since Unbridled in 1990 to win the Kentucky Derby and the Breeders’ Cup Classic in the same year.