Ultimate Kentucky Derby Race: Secretariat Humbles the Field

The 150th Kentucky Derby goes on Saturday, with excitement building for the milestone event. One of the 20 horses in the Churchill Downs starting gate will be forever remembered as part of history alongside 149 other “Run for the Roses” winners.

Some of the 149 prior champions have shone more brightly than others, burning themselves perpetually into the minds of horseplayers and fans. 

For many, American Pharoah jumps out as an all-timer that broke the long drought between Triple Crown winners. For others, Secretariat has built a legacy that's impossible to surpass. There are several Kentucky Derby winners in between the two that are also in the National Museum of Racing and Hall of Fame, including Triple Crown winners Seattle Slew and Affirmed.

Assembling a field of only 20 runners from 150 possibilities (including this year’s favorite, Sierra Leone) to make the Ultimate Kentucky Derby is a daunting task, but I’ve done my best to separate the wheat from the chaff. Tough cuts were made, including Triple Crown winner Justify, who was recently disqualified from the Santa Anita Derby win that gave him a berth into the Kentucky Derby and cost him his perfect 6-for-6 record.

The remaining 12 Triple Crown champions all made the cut, meaning there were only seven “at large” bids to be had among former Derby winners. As a result, legends like Ben Brush, Old Rosebud, Regret, Zev, Black Gold, Reigh Count, Twenty Grand, Cavalcade, Johnstown, Needles, Tim Tam, Carry Back, Majestic Prince, Foolish Pleasure, Genuine Risk, Alysheba, Winning Colors, Sunday Silence, and Silver Charm all fell short.

Here’s the field of legends set to the compete in the Ultimate Kentucky Derby.

And for more on the 2024 Kentucky Derby, head over to our Kentucky Derby picks and predictions, Kentucky Derby odds, and Kentucky Derby post positions.

Ultimate Kentucky Derby field

Hindoo (1881, no Triple Crown)

Comparing Hindoo to the rest of the horses on the list is a bit like comparing apples and oranges. But the member of the inaugural 1955 Hall of Fame class should not be overlooked.

Hindoo reeled off 18 straight wins, including the Kentucky Derby (then run at 1.5 miles), at age three. All told, he compiled 30 wins (26 stakes) from 35 starts while never failing to hit the board.

Exterminator (1918, no Triple Crown)

A true war horse, Exterminator accumulated 50 wins from 100 career starts. Several of his most significant victories came in long-distance races, including his four consecutive triumphs in the 1.75-mile Saratoga Cup.

Exterminator was a 29/1 long shot when he won the Derby in his first start as a three-year-old.

Sir Barton (1919, Triple Crown)

Competing in the Kentucky Derby as a maiden, Sir Barton took the field gate-to-wire. He ran in the Preakness just three days later and won again. And after taking the Withers Stakes in between, Sir Barton became the first horse to win the Belmont Stakes along with the Derby and the Preakness, a feat that would retroactively come to be known as the Triple Crown.

Hoof problems prevented Sir Barton from being consistently great, but he did beat Exterminator later at age three in the Saratoga Handicap and lowered a Saratoga track record in the Merchants and Citizens Handicap.

Gallant Fox (1930, Triple Crown)

Gallant Fox demonstrated plenty of talent at two while taking a pair of stakes. But he was seen as inferior to a horse named Whichone, who beat him head-to-head in the Belmont Futurity. Gallant Fox would settle the score in the Belmont Stakes, but not before taking the Preakness and the Kentucky Derby (in that order) to become the second-ever Triple Crown winner.

After also posting wins during the Wood Memorial, Withers Stakes, Dwyer Stakes, Arlington Classic, Saratoga Cup, Jockey Club Gold Cup, and Lawrence Realization Stakes, Gallant Fox amassed a then-world record $317,865 in earnings before being retired.

Omaha (1935, Triple Crown)

Omaha became the first Triple Crown winner that a fellow Triple Crown winner sired (Gallant Fox) when he took the Kentucky Derby, Preakness Stakes, and Belmont Stakes in 1935.

Omaha won several more stakes in his career, but arguably his greatest achievement came in defeat when he lost by just a head in the 1937 Ascot Gold Cup while going 2.5 miles on turf at Royal Ascot.

War Admiral (1937, Triple Crown)

War Admiral became the third and final Triple Crown winner of the 1930s. His Derby, Preakness, and Belmont wins were part of an incredible 18-for-20 run to close out his career. The only losses came on a “heavy” track in the Massachusetts Handicap and to the legendary Seabiscuit in a match race in the 1938 Pimlico Special.

Man O'War sired War Admiral, and some believe the former is the greatest racehorse of all time, and his influence on the thoroughbred pedigree has been long-lasting. American Pharoah and Justify, among others, trace their roots back to him.

Whirlaway (1941, Triple Crown)

Whirlaway is still the only horse to win the Triple Crown as well as the Travers Stakes, a feat not even Secretariat or American Pharoah can boast. He also owns the co-largest margin of victory in the Kentucky Derby (eight lengths).

Whirlaway entered 60 races in his career while winning 32 (20 stakes) and hitting the board in 24 others.

Count Fleet (1943, Triple Crown)

Count Fleet, whom Derby winner and Hall-of-Famer Reigh Count sired, began his career with two losses before getting his act together. He won 10 of 15 starts at age two, which will probably never happen again.

Count Fleet injured himself after winning the Wood Memorial ahead of the Kentucky Derby, but he recovered in time to take the “Run for the Roses” and participate in the Preakness and the Belmont. He scared off many rivals and may have been on his way to all-time great status. But frequent injuries forced him to retire after his staggering 25-length victory in the “Test of the Champion.”

Assault (1946, Triple Crown)

Assault was unusual after being bred in Texas, and he developed a “club foot” due to an injury suffered as a weanling. Despite his less-than-regal appearance and pedigree, Assault proved the doubters wrong after recording an eighth-length victory in the Derby (a record he shares with Old Rosebud, Johnstown, and Whirlaway) before taking the Preakness and the Belmont while becoming the seventh Triple Crown winner.

He went on to be a solid handicap horse in 1947. And although he took his fair share of losses later in his career before retiring at age seven, Assault still stands as a legend of the sport.

Citation (1948, Triple Crown)

The first million-dollar earner in horse racing history, Citation showed rare ability from a young age before sustaining it over several years. He won eight of nine starts at age two, then beat 1947 Horse of the Year Armed as a three-year-old before even getting to the Kentucky Derby.

Citation took all three Triple Crown races in style, scaring away plenty of competitors. All told, he won 19 of 20 starts as a three-year-old. Success at age four and beyond allowed him to stake his claim as an all-time great.

Swaps (1955, no Triple Crown)

Known as the “California Comet,” Swaps sped away from the competition in 19 of 25 career starts with only two off-the-board efforts.

East coasters highly regarded Swaps, though they preferred Nashua in the 1955 Kentucky Derby. But Swaps was a game gate-to-wire winner over that rival. Although Nashua would get his revenge in a match race later that year, Swaps would go on to set multiple track records before calling it quits.

Injuries would truncate his career, as Swaps didn't get the chance to compete in the Preakness or Belmont.

Northern Dancer (1964, no Triple Crown)

The pride of Canada, Northern Dancer was never out of the money in 18 career starts and won 14 times. That includes the 1964 Kentucky Derby, when the undersized but talented colt held off a late rally from favored Hill Rise to win in 2:00 flat, which stood as the Kentucky Derby record until 1973.

Northern Dancer won the Preakness, once again beating Hill Rise and Belmont Stakes winner Quadrangle. While Northern Dancer could only be third in the Belmont, he did go back to Canada to become the first and only winner of both the Derby and the Queens Plate before injuries cut his career short.

Riva Ridge (1972, no Triple Crown)

It could be argued that without Riva Ridge, there would be no Secretariat as we know him today. Riva Ridge’s success in 1971 and 1972 was largely responsible for saving Meadow Stable from going bankrupt.

After taking championship honors as a juvenile, Riva Ridge won two of three Kentucky Derby preps before going gate to wire in America’s biggest race. A sloppy track stopped him from attaining Triple Crown glory in the Preakness, but ‘Ridge came back to crush the competition in the Belmont.

Secretariat (1973, Triple Crown)

Not only did Secretariat become the first Triple Crown winner since 1948, but he did so while setting stakes records in all three legs. His 31-length victory in the Belmont Stakes is the stuff of legends.

Though he didn't race at age four like the majority of horses on this list, there wasn't much left to prove after posting Grade I wins on both turf and dirt at various distances. To many, he's not only the greatest Derby winner, but the best thoroughbred that ever raced.

Seattle Slew (1977, Triple Crown)

Officially, Seattle Slew is the only horse to ever win the Triple Crown while still undefeated.

Seattle Slew would taste defeat just three times over 17 starts, and he had legitimate excuses each time. Even in his defeat in the 1978 Jockey Club Gold Cup, Seattle Slew was able to beat fellow Triple Crown winner Affirmed, which was the second time he finished ahead of that rival.

Affirmed (1978, Triple Crown)

Though Affirmed was unable to get the better of Seattle Slew, his accomplishments still shine. He won 22 of 29 starts, and in each leg of the Triple Crown another legend of the turf in Alydar hounded him. He faced Alydar 10 times and beat him on seven occasions (one loss was via a controversial DQ).

Affirmed enjoyed a dominant four-year-old season, handing Spectacular Bid a rare loss en route to becoming the first $2-million earner in the sport.

Spectacular Bid (1979, no Triple Crown)

Perhaps the greatest non-Triple Crown winner on this list, Spectacular Bid tasted defeat only four times in 30 career starts, and just twice after turning three. ‘Bid might have won the Belmont but for an incident in which he stepped on a safety pin in the build-up to the race, leading to an infection.

Spectacular Bid demonstrated greatness in easy wins during both the Derby and the Preakness, and later victories in the Santa Anita Handicap and more.

California Chrome (2014, no Triple Crown)

California Chrome captivated the nation while outrunning his humble pedigree and then some.

He produced mixed results at age two but seemed to find a home racing against California-bred opponents. However, he turned a corner at age three while starting to rack up wins against open company, including a convincing victory in the Santa Anita Derby. He would become the first California bred since 1962 to win the Kentucky Derby, and California Chrome followed it up with a comfortable score in the Preakness.

Though he was unable to pass the “Test of the Champion” while finishing fourth in the Belmont, Chrome won four more Grade/Groups before retiring, including the Dubai World Cup.

American Pharoah (2015, Triple Crown)

A fifth-place finish in his debut showed what a special horse American Pharoah would become, as he ended his career on a 10-for-11 run.

Pharoah did what many were beginning to think was impossible when he captured the Derby, Preakness, and Belmont, making him the first Triple Crown winner since 1978. His only loss since that unceremonious unveiling was a hard-luck second to Keen Ice in the Travers.

American Pharoah would shake off that loss while taking the Breeders’ Cup Classic, putting on a bow on his captivating career.

Sierra Leone (2024 Kentucky Derby favorite)

The odds-on favorite to win the 2024 Kentucky Derby might not possess nearly the same pedigree as the remainder of the competitors in this field. But anything can happen in a mile and a quarter. Trainer Chad Brown has experienced his fair share of triumphs in horse racing's most significant events, so don't rule out a strong finish from Sierra Leone.

Ultimate Kentucky Derby post draw and odds

Handicapping a field with such an incredible pedigree is difficult. But post position can guide us.

We put the names of all 20 horses into the list randomizer at , then shuffled the list 20 times to come up with our starting list. Here's a look at the post position results for our Ultimate Kentucky Derby race, along with the pre-race odds:

The picture becomes a little clearer with the starting positions settled. Despite opening from a 14-spot that's produced just two Derby winners (and none since 1961), Secretariat's reputation wins out en route to a field-best 3/1 odds entering the competition.

The other major headliner, 1948 Triple Crown winner Citation, drew an even less celebrated position. No horse has won a Kentucky Derby from the No. 17 spot. It's the only starting position in the race that's failed to produce a winner, though we may see a real-life end to that streak with Todd Pletcher's Fierceness (5/2) opening from the No. 17 position Saturday.

The three other horses in the top five in implied probability are bunched together, with Affirmed, Seattle Slew, and Spectacular Bid starting at Nos, 6, 7, and 9, respectively.

Ultimate Kentucky Derby race results

With the field set, the horses warmed up, and bettors done at the window, it's time to see who is the greatest Kentucky Derby champion in history, as chosen by ChatGPT.

(Click the image below for the complete race simulation.)

As expected, the two race favorites hit the one-quarter mark dead even, with the next wave of contenders already two-tenths off the pace. The most surprising result to this point in the race is Spectacular Bid more than a half-second behind the co-leaders despite entering the Derby as an 8/1 challenger.

Citation does well to keep Secretariat honest at the halfway point, while Seattle Slew loses only a tenth of a second to solidify its hold on third place. Surprisingly (or not so much, depending on how you frame Secretariat's historical dominance), only five horses are within less than a second of the awesome favorite.

We see the brute athleticism of Secretariat take over once the race passes the halfway point. The legendary racehorse opens up an eight-tenths lead on a game Citation, while the rest of the field begins to lose even more ground. Notably, Affirmed surges past several contenders over this quarter to move into the show position before ultimately fading down the stretch.

Secretariat saves its best for last, showing the kind of finishing kick reserved for the greatest racers ever. It obliterates the most impressive field in Kentucky Derby history, finishing more than a second ahead of runner-up Citation and nearly two seconds faster than every other competitor. American Pharaoh blazes across the line in third, edging out Seattle Slew.

Ultimate Kentucky Derby time intervals

**James Bisson contributed to this feature.