Stars of Yesterday: Trying Again at Greatest Insurgent Stakes Winners

The Highway to the Kentucky Derby Introduced by Woodford Reserve winds its approach by Oaklawn Park this Saturday, for the $1.25 million, Grade 2 Insurgent Stakes. A aggressive subject of 13 entrants is ready to line up for this 1 1/16-mile occasion, with 50 qualifying Derby factors going to the winner.

The race was inaugurated in 1961 because the Insurgent Handicap, and was modified to the Insurgent Stakes in 1984. That very same yr, the gap was adjusted from one mile and 70 yards to 1 1/16 miles. In 1990, the race was given Grade 3 standing, however was ungraded in 2003 and 2004. It was upgraded to Grade 2 in 2008.

Lately, this race has seen dramatic purse will increase. In 2011, the race carried a handbag of $300,000. By 2016, the purse had tripled to $900,000. It was held as a $1 million race for the primary time in 2020 and elevated once more by 1 / 4 of 1,000,000 {dollars} in 2024. Because of its lofty purse, its record of high-profile winners together with Triple Crown winner American Pharoah, and its 50-25-15-10-5 allocation of Derby qualifying factors, the Insurgent is assured to be one of many season’s main Kentucky Derby prep races.

Right here, we’ll have a look again at a number of the finest winners of the Insurgent Stakes.


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


Temperence Hill started his profession inauspiciously as a 2-year-old, lacking the board in three begins in New York. To start his 3-year-old season, he was despatched to Oaklawn Park, the house base of his house owners, Loblolly Secure. Off two straight wins, he was despatched to the Insurgent Handicap for his stakes debut.

Bettors thought little of his possibilities, sending him off at 16.50-1. He was far behind early on, 17 lengths off the chief after the opening quarter-mile. Nevertheless, as they turned for residence he discovered one other gear and charged exhausting after pacesetter Be a Prospect. That one had no response, and Temperence Hill cruised by him and drew off to a 2 ¼ size win underneath jockey Darrell Haire.

Two begins later, Temperence Hill received his first graded stakes with a 1 ¼-length win within the Arkansas Derby. Nevertheless, he was not nominated for the Kentucky Derby so he was pressured to sit down that race out. After defeats in two graded stakes races, Lobolly Secure and coach Joseph Cantey determined to take a shot within the Belmont Stakes. Temperence Corridor was not nominated for that race both, so that they needed to pay a $5,000 supplemental payment on prime of the $15,000 entry payment. He was thought-about a rank 53.40-1 outsider. Preakness winner Codex was the 8-5 favourite.

Nevertheless, Temperence Hill pulled off a shock. Underneath Eddie Maple, he wore down Kentucky Derby-winning filly Real Threat within the stretch to win by two lengths, paying a whopping $108.80 to win. Proving that he was no fluke traditional winner, Temperence Hill received the Travers Stakes, the Jockey Membership Gold Cup, and the Tremendous Derby. At yr’s finish, he received the Eclipse Award for champion 3-year-old male.


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


The Canadian-bred Sunny’s Halo did his finest work in his residence nation in 1982, the place at his residence base of Woodbine he received 4 stakes races. These wins earned him the Sovereign Award because the champion 2-year-old male in Canada. His American physique of labor, nevertheless, left one thing to be desired. In 4 stakes tries in the US at age 2, he managed to complete within the prime three simply as soon as, nabbing third within the Tremont Stakes at Belmont Park. Because of this, he was not considered a severe Derby prospect going into the 1983 path.

Sunny’s Halo didn’t make his 3-year-old debut till the March 26 Insurgent. He went off as second alternative within the subject of 11. Jockey Larry Snyder rated him off the leaders early after which moved after them on the flip. From there, Sunny’s Halo drew off to a three-length victory.

Subsequent out, Sunny’s Halo received the Arkansas Derby by 4 lengths underneath Eddie Delahoussaye. Regardless of the spectacular wins, there have been nonetheless some questions on Sunny’s Halo earlier than the Derby. At the moment no horse had received each the Arkansas Derby and the Kentucky Derby. Some bettors had been additionally involved a couple of lack of basis, as he had solely two begins as a 3-year-old earlier than the Derby. Regardless of the doubts, Sunny’s Halo was the 5-2 second favourite.

The doubters had been silenced after the race, as Sunny’s Halo bought a fantastic stalking journey and drew off to a two-length win underneath Delahoussaye. He turned the primary Canadian-bred horse to win the Derby since Northern Dancer in 1964.


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


4 years after Temperence Hill, Loblolly Secure was again with one other up-and-coming 3-year-old. In his Oaklawn Park debut the race earlier than the Insurgent, Vanlandingham impressively defeated an allowance subject by 10 lengths. Off the power of that win, he was made the 6-5 favourite within the Insurgent.

Vanlandingham lived as much as all expectations within the Insurgent. Though he needed to grind a bit within the stretch, Vanlandingham pulled clear within the final eighth for a 1 ¼-length victory with Pat Day within the irons. He lined the 1 1/16 miles in a powerful 1:41.

He was scratched from the Arkansas Derby because of sickness however recovered in time to compete within the Kentucky Derby. Together with stablemate Pine Circle, he represented the primary Derby starters for Loblolly Stables and their coach, Shug McGaughey. They had been coupled within the wagering, and given a robust 6-1 likelihood. Sadly, Pine Circle was a nonthreatening sixth, whereas Vanlandingham fractured a pastern bone in the course of the race and completed sixteenth.

Whereas the harm price him the remainder of his 3-year-old season, Vanlandingham returned higher than ever at age 4. In his third begin off the layoff, he received the Suburban Handicap by 8 ¾ lengths. Later that yr, he received the Jockey Membership Gold Cup by 2 ½ lengths, changing into the primary a number of Grade 1 winner educated by McGaughey. Though he was a disappointing seventh within the Breeders’ Cup Traditional, a win on grass within the Washington D.C. Worldwide restored his repute and helped him win the Eclipse as champion older male.


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


After a little bit of a sluggish begin to his profession, Pine Bluff discovered his finest stride in direction of the tip of his 2-year-old marketing campaign. He capped off his 1991 season with wins within the Remsen and Nashua Stakes at Aqueduct.

In his 3-year-old debut, he was second within the Southwest Stakes behind upset winner Large Sur. Bettors weren’t deterred by that defeat and made him the 3-10 favourite within the Insurgent Stakes subsequent out. With Jerry Bailey within the saddle, Pine Bluff moved to have interaction pacesetting Desert Pressure and despatched him by robust fractions. They went the opening quarter-mile in 23.14 seconds and adopted 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.

Within the final eighth of a mile, though Desert Pressure continued to struggle, Pine Bluff bought the higher hand and pulled clear late for a 2 ½-length win, finishing the 1 1/16 miles in 1:42.83.

For his closing Derby prep, Pine Bluff was the 4-5 favourite within the Arkansas Derby. He as soon as once more needed to duel, this time with Lil E. Tee, however he prevailed in a protracted stretch battle to win by a neck. Within the Kentucky Derby, Pine Bluff was the ten.50-1 third alternative with Craig Perret, who rode him as a 2-year-old, getting again within the stirrups. He completed fifth as Lil E. Tee turned the tables with a Derby upset.

For the Preakness Stakes, Pine Bluff bought one other new jockey as Chris McCarron took over driving duties. He was the slim 7-2 favourite within the full subject of 14 and lived as much as expectations. Perret, driving Alydeed, opened up a transparent lead within the final eighth, however McCarron and Pine Bluff chased him down, rallying for a three-quarter-length victory. It was the primary Triple Crown race win for Loblolly since Temperence Hill’s Belmont.


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


As a 2-year-old, Victory Gallop received two stakes races at Colonial Downs, making robust rallies from behind each occasions. He concluded his 2-year-old season with a monster second-place end within the Laurel Futurity, the place he closed from second regardless of being tempo compromised with a large journey.

After that large race, Victory Gallop was bought privately by Prestonwood Farm, which transferred him to the care of Elliott Walden. He made his first begin for the brand new connections within the Insurgent Stakes in late March. He was the 4.10-1 third alternative in a wide-open betting race.

Jockey Eibar Coa saved him pretty near the tempo as longshots Robinwould and Slew the Mark set average fractions. As the sphere rounded the far flip, Coa requested his mount for run within the three path and he moved to have interaction the leaders. He moved previous Slew the Mark simply, however Robinwould dug in on the within and wouldn’t let him by and not using a struggle. Victory Gallop held on to win by a head.

Following one other hard-fought win within the Arkansas Derby, Victory Gallop was not extremely regarded going into the Kentucky Derby. At 14.60-1, he rallied from lifeless final to complete second, crushed half a size by Actual Quiet. As the favourite within the Preakness Stakes, he as soon as once more closed for second, however Actual Quiet prevailed once more to set himself up for a Triple Crown bid within the Belmont Stakes.

That Belmont proved to be some of the dramatic editions within the race’s historical past. Kent Desormeaux moved Actual Quiet to the lead early on and drew off from the remainder because the horses rounded the ultimate flip, with five-sixteenths of a mile nonetheless to run. Victory Gallop, underneath Gary Stevens, remained effectively out of it, however started to hit prime gear as they turned for residence. Within the stretch, Actual Quiet started to tire whereas Victory Gallop flew down the stretch in his bid to thwart historical past. Although Actual Quiet lugged out within the stretch into Victory Gallop’s path, Victory Gallop closed powerfully to win, denying Actual Quiet the Triple Crown.

Though Victory Gallop couldn’t take the champion 3-year-old male Eclipse away from Actual Quiet, he took residence year-end honors at age 4. He received two Grade 1s in 1999, together with a dramatic stretch battle within the Whitney Handicap over Behrens, to win the Eclipse as champion older male.


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


For his or her 100th anniversary in 2004, Oaklawn Park determined to boost their highway to the Kentucky Derby. They introduced that if a horse swept the Insurgent Stakes, the Arkansas Derby, and the Kentucky Derby they might win a $5 million bonus.

That supply proved very engaging for Pennsylvania-bred Smarty Jones. He received his first three begins, racing at Philadelphia Park (now recognized at Parx Racing) and Aqueduct, by a mixed 27 ¾ lengths. Though his proprietor, Sometime Farm, and coach, John Servis, had been East-Coast based mostly they determined to ship their prized colt to Oaklawn to arrange for a Derby run.

In his first Oaklawn begin, Smarty Jones received the Southwest Stakes by three-quarters of a size. Regardless of his unblemished document, he didn’t command that a lot respect on the betting home windows on Insurgent Stakes day. He was the 7-2 third alternative behind the much-hyped Todd Pletcher trainee Purge and Honest Grounds shipper Mr. Jester.

Purge went out to the lead, whereas Stewart Elliott rated Smarty Jones simply off the chief’s flank in second. As the sphere rounded the far flip, Purge maintained a slender benefit however Smarty Jones continued to edge nearer. Purge had no response within the final eighth, and Smarty Jones pulled away for a 3 ¼-length victory.

Following a dominant win within the Arkansas Derby, Smarty Jones went to Louisville because the Kentucky Derby favourite, with a shot to change into the primary undefeated Derby winner since Seattle Slew in 1977. On a sloppy observe, he wore down pacesetting Lion Coronary heart for a 2 ¾-length victory, clinching the $5 million bonus.

Smarty Jones then received the Preakness Stakes in dominant trend, setting himself as much as change into the primary Triple Crown winner in 26 years. A crowd of greater than 120,000 confirmed as much as Belmont Park for the Belmont Stakes to cheer on the favored Pennsylvania-bred. He misplaced to late-running upset winner Birdstone in some of the memorable Triple Crown races of this century.

CURLIN (2007)

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

CAREER EARNINGS: $10,501,800

Curlin was on the nationwide racing scene from the second he made his debut. He received his first begin at Gulfstream Park in February 2007 by 12 ¾ lengths, going seven furlongs in 1:22.25. After that win, Stonestreet Stables bought an 80% share within the colt for $3.5 million and transferred him to coach Steve Asmussen.

For his second begin, Curlin was instantly despatched into the deep finish, and went off because the second betting alternative within the Insurgent Stakes. Towards a more durable subject and stretching out round two turns for the fist time, he was simply as spectacular. He made a giant, four-wide sweep on the flip and powered away in stretch for a dominant 5 ¼-length win. Immediately, Curlin turned one of many Kentucky Derby favorites.

In his closing tune-up for the primary Saturday in Might, Curlin received the Arkansas Derby by 10 ¼ lengths. Regardless of not racing at age 2 and with solely three begins underneath his belt, Curlin was the 5-1 second alternative within the Kentucky Derby. He completed third behind Avenue Sense, however avenged that defeat with a win within the Preakness Stakes. Curlin misplaced an exciting Belmont Stakes to the filly Rags to Riches, however later that yr he received the Jockey Membership Gold Cup and the Breeders’ Cup Traditional to clinch the Horse of the Yr title.

As a 4-year-old in 2008, Curlin added one other Horse of the Yr title to his résumé, notching 4 Grade or Group 1 wins. He additionally turned the primary American-based horse to go $10 million in profession earnings.


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


Lookin At Fortunate received the Eclipse for champion 2-year-old male for 2009 on the power of 4 stakes wins. Had been it not for a head defeat within the Breeders’ Cup Juvenile, he would have had an ideal season. Even so, he loomed as a severe Derby prospect going into his 3-year-old debut within the Insurgent Stakes.

Regardless of his spectacular résumé, Lookin at Fortunate was not the overwhelming favourite. Dublin, off a second-place end within the Southwest Stakes, was the 7-5 second alternative. Lookin At Fortunate, in the meantime, closed because the 11-10 favourite. Within the race, Lookin At Fortunate rated off the tempo a number of paths of the rail after which moved vast within the stretch. On the eighth pole he remained in third, nonetheless two lengths behind dueling Dublin and Noble’s Promise. Whereas Dublin light within the closing sixteenth of a mile, Noble’s Promise remained robust on the lead. Underneath vigorous urging from Garrett Gomez, Lookin At Fortunate wore down Noble’s Promise within the final stride to win in a photograph end. That win gave coach Bob Baffert the primary of his seven Insurgent wins.

After a third-place end within the Santa Anita Derby and a sixth-place effort within the Kentucky Derby, Lookin at Fortunate’s star dimmed a bit. He bounced again in his subsequent begin with a sport three-quarter-length Preakness Stakes win. He then tallied two extra graded stakes wins in 2010 and earned one other Eclipse championship, this time for prime 3-year-old male.


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


Getting into the 2013 Insurgent Stakes, Will Take Cost was a combined bag. He started his 3-year-old season with a win within the Smarty Jones Stakes and was second within the Remington Springboard Mile within the race earlier than. Nevertheless, the D. Wayne Lukas trainee went into the Insurgent off a dismal sixth-place end within the Southwest Stakes, crushed 18 lengths by Tremendous Ninety 9. Will Take Cost was a 28-1 outsider going into the Insurgent whereas Tremendous Ninety 9 was wager right down to 6-5 favoritism.

Will Take Cost was sixth within the early levels, racing about three lengths off pacesetting Title Contender. On the ultimate flip, Tremendous Ninety 9 and Oxbow (Will Take Cost’s stablemate) drew away from the remainder of the sphere whereas Will Take Cost was third. Tremendous Ninety 9 light within the final eighth and Oxbow pulled clear. Underneath a drive from Jon Court docket, Will Take Cost surged on the chief late and rallied to defeat Oxbow by a head and pull off the upset.

After that win, Will Take Cost competed in all three Triple Crown races, ending no higher than seventh in any of them. Oxbow went on to win the Preakness and Will Take Cost completed 16 lengths behind, however Oxbow tailed off after that. Conversely, Will Take Cost caught fireplace for “the Coach” towards the tip of the season. He received the Travers Stakes, the Pennsylvania Derby, and the Clark Handicap whereas additionally ending second by a nostril within the Breeders’ Cup Traditional on his strategy to an Eclipse Award.


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


Regardless of not racing within the Breeders’ Cup, Bob Baffert-trained American Pharoah was voted champion 2-year-old male of 2014 based mostly on two Grade 1 wins in California. He made his comeback within the Insurgent Stakes, the place he was made the overwhelming 2-5 favourite within the subject of seven.

American Pharoah recovered rapidly from a foul break and went instantly to the entrance. By the point he reached the opening quarter, he was 1 ½ lengths in entrance and setting very average fractions. None of his rivals had a lot hope of catching him and he opened up an increasing number of with each stride. On a really sloppy observe, he crossed the end line 6 ¼ lengths away from the others, stopping the clock in 1:45.78.

The Insurgent proved to be a launching pad for an awe-inspiring marketing campaign. That summer time, American Pharoah swept his approach by the Triple Crown, changing into the primary horse to win the Kentucky Derby, the Preakness Stakes, and the Belmont Stakes since Affirmed in 1978. Because the cherry on prime, he accomplished his yr with a dominant Breeders’ Cup Traditional win. With that victory, he turned the primary horse since Unbridled in 1990 to win the Kentucky Derby and the Breeders’ Cup Traditional in the identical yr.

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