Ranking Horse Racing’s Triple Crown Winners: Who’s the Best?

Triple Crown season always brings renewed hope of another immortal horse and a chance to walk down horse racing’s Memory Lane and revisit the 13 immortals that have conquered this test of a champion. And speaking in glowing terms of past-greats is quaint and all, but which horses were the best of the best?

13. Sir Barton | 1919

Kentucky Derby Odds: 5/2

Preakness Odds: 14/5

Belmont Odds: 2/5

Poor Sir Barton. He’s the sport’s first Triple Crown Winner and most casual fans know little more about him than his name at that he was the first. Aside from being the first, the manner in which he won the Triple Crown was something you’ll never quite see again.

He won the Kentucky Derby in his first race of the year. He also threw in a win in The Withers after the Preakness, which barely seemed to work him into a sweat, considering his final time of 2:17 and 2/5ths for 11 furlongs in the subsequent Belmont Stakes (yes, it was shorter back then) was the fastest any horse had ever run the distance in the U.S.

By all accounts he was a magnificently accomplished horse who was supremely talented but unfortunately overshadowed in his day by Man O’ War. They match-raced. Sir Barton lost and therefore he was relegated to never being better than the second-best racehorse of his generation.

He was also considered the second- best racehorse from his own barn in the Kentucky Derby that year, having been entered as a rabbit for stablemate Billy Kelly. But the rabbit never came back that day and the rest is a history.

12. Omaha | 1935

Kentucky Derby Odds: 4/1

Preakness Odds: 19/20

Belmont Odds: 4/5

Omaha was the second Triple Crown winner for trainer Sunny Jim Fitzsimmons, sired by his first Triple Crown winner, Gallant Fox. He was only the third horse to pull off this test of champions and was immediately hailed as an all-time great. Five of his six career stakes victories came during his 3 year-old campaign, and his Preakness victory nearly matched the track record.

However, his loss in the Dwyer stakes cost him Horse Of The Year honors and he remains the only Triple Crown winner to not be recognized as such.

11. Assault | 1946

Kentucky Derby Odds: 8/1

Preakness Odds: 7/5

Belmont Odds: 7/5

Assault’s Derby victory left racing fans and turf writers with plenty to interpret. His eight-length margin of victory was the biggest in the race’s history but the sluggish time of 2:06 and 3/5ths was more than five seconds off Whirlaway’s track record.

He didn’t break any land-speed records in the Preakness either as the time of 2:01 and 2/5ths wouldn’t have broken Whirlaway’s record with a half-furlong head start. The Belmont Stakes was an equally pedestrian 2:30 and 4/5ths leaving the door open for humans to denigrate one of the great accomplishments in equine sport.

His story is an amazing tale as he overcame a disfigured foot that left him limping throughout his entire life. He was deemed “the club-footed comet” and although the limp was evident in his walk, his stride at full gallop was reportedly as perfect as any racehorse could hope for.

10. Justify | 2018

Kentucky Derby Odds: 5/2

Preakness Odds:1/2

Belmont Odds: 3/5

Justify is a tough gun to calibrate. His accomplishment in winning the Triple Crown is perhaps too unique in modern context to quantify accurately. He was the only other undefeated Triple Crown winner outside of Seattle Slew. He broke the Curse of Apollo by winning the Derby without racing at age 2. He debuted in February and was gone after the Belmont leaving most of in the industry asking “What the hell did we just see?”

The double-edged sword for this shooting-star of a career is the lack of context for his accomplishment. He was undoubtedly a brilliantly talented colt and the most impeccable physical specimen in world. He was giant both literally and figuratively, but the brevity of his career left the door open for a lot of questioning.

Is he truly an all-time great or did they just catch lightning in a bottle with a supremely athletic horse going on a tear at the right time? Does the lack of consistency from his competition in the second half of 2018 take a little shine off this Cadillac?

Ultimately it doesn’t matter so long as you enjoyed the ride with the knowledge that you’ll never see what he did again. And if it weren’t for Pharoah winning the Triple Crown three years earlier, Justify’s brilliance wouldn’t be questioned at all.

9. Gallant Fox | 1930

Kentucky Derby Odds: 6/5

Preakness Odds: 1/1

Belmont Odds: 8/5

Gallant Fox was the first horse to be deemed the Triple Crown winner by turf-writer Charles Hatton. The 1930 Horse of The Year had a silly campaign with victories in the Wood Memorial, Derby, Preakness, Belmont, Dwyer, Arlington Classic, Saratoga Cup and the Jockey Club Gold Cup going 9-for-10 in 1930.

The only blemish on his sparkling résumé was perhaps the most famous race of his career when he lost the Travers to 100-1 long shot Jim Dandy at Saratoga (how a horse went off at 100-1 in a three-horse field is another question entirely). It was widely considered the greatest upset in racing history, even greater than when Upset upset Man O’ War.

He also won the Preakness eight days before winning the Derby which in recent years has given some credence to those who wanted to switch up the dates to make the Triple Crown easier (Pharoah and Justify have quieted such arguments, clearly).

8. American Pharoah | 2015

Kentucky Derby Odds: 5/2

Preakness Odds: 4/5

Belmont Odds: 3/5

After experiencing American Pharoah firsthand, many will have a hard time with him being so low on this list. He was the perfect horse: fleet-footed, well-bred, beautiful to look at with the disposition of a well-trained golden retriever.

Unlike Justify, who was here and gone before you knew it, American Pharoah’s precocity was well-documented before his debut. Bob Baffert had not been shy about touting Pharoah as his best 2-year-old at Del Mar, a fact which left many scratching their heads after his disappointing fifth in his debut. He wouldn’t lose again for another year.

No horse ever really matched up with Pharoah. Firing Line actually gave him a stiff run in the Derby but succumbed by a length at the wire and was never the same horse after that. American Pharoah would go on to easily sweep through the final two jewels, romp home in the Haskell and then run the fastest race in his career when beating older horses in the Classic at Keeneland.

His lone stakes defeat came in the Travers at the hands of Frosted and Jose Lezcano, who picked up the mount after Joel Rosario got hurt. Keen Ice won the race, but Frosted took it to Pharoah early and left him vulnerable in the toughest 220 yards in racing, the 10th furlong at The Graveyard of Favorites.

7. Affirmed | 1978

Kentucky Derby Odds: 9/5

Preakness Odds:1/2

Belmont Odds: 3/5

Affirmed was the last Triple Crown Winner of the 20th century and those roaring 70s that saw three pull off the toughest triple in racing. It’s impossible to mention his career without immediately conjuring up images of his famous battles with Alydar.

Nine times Affirmed and Alydar finished in the top-two in graded stakes races. Alydar was actually favored in the 1978 Run For The Roses after a monster performance in the Blue Grass, but Affirmed of course would go on to win and set the stage for 2 of the greatest Triple Crown races in history.

The 1978 Preakness and Belmont stakes are as sensational as sporting events get: throw-down battles on the track between two of the greatest horses of all-time with the Triple Crown hanging in the balance. Affirmed would go on to win Horse Of The Year honors and tally up 19 stakes victories that tallied over $2,000,000 in career earnings.

6. War Admiral | 1937

Kentucky Derby Odds: 8/5

Preakness Odds: 7/20

Belmont Odds: 4/5

War Admiral is known to a generation of movie-goers as the villain in the 2003 Box Office hit “Seabiscuit.” And yes, he lost the famous match-race to the undersized Biscuit in real life as he did in the movie, but let’s not forget why he was such a Goliath in the first place.

His sire, the great Man O’ War, was considered the greatest race horse of the century. His owner, Samuel Riddle, was not much for running in the Derby, finding the 10-furlong distance too taxing for 3-year-olds so early in the year. But War Admiral saw his owner have a change of heart that led him into the race his sire never ran.

His Triple Crown was notable for his speed and perseverance, as his record-setting time in the Belmont Stakes was accomplished after having grabbed a quarter out of the gate and crossing the finish line with blood on all four legs. The injury caused him to miss several months but he returned to win three races in the fall, including the Pimilico Special, en route to being crowned Horse of The Year.

At the end of the day, the Seabiscuit match race is a nice story and all, but War Admiral was most likely the better horse. He was a faster animal but had a horrendous gate temperament that caused him to jump backwards when Tom Smith, Seabiscuit’s trainer, decided to invent and implement the Starting Gate Bell for the first time ever in that race.

Once Biscuit had the lead, War Admiral was at a tremendous disadvantage. He’s not only a top-10 Triple Crown horse, but he’s easily a top-10 racehorse of the 20th Century.

5. Whirlaway | 1941

Kentucky Derby Odds: 19/10

Preakness Odds: 23/20

Belmont Odds:1/4

Whirlaway was a national hero in 1941 and 1942 when he was two-time horse of the year at ages 3 and 4. Racing during World War II, he famously raised over $5,000,000 during his 4 year-old campaign running for war bonds.

His career earnings of $561,161 were a record at the time of his retirement and his Derby time of 2:01 and 2/5ths was a record that stood for more than two decades (his final quarter was a ridiculous 23 and 3/5ths).

He was also the greatest training accomplishment of Hall of Fame trainer Ben Jones’ career. He was beyond a difficult horse to teach and had a tendency to lug out badly, leading to his trainer’s invention of a one-eyed blinker on the right side of his head. But when he ran, he obliterated his competition.

He won the Derby by eight lengths, spotted the field six lengths in the Preakness and swooped by them all to win by more than five, and then made an early move in the Belmont to take the Triple Crown in a laugher.

4. Count Fleet | 1943

Kentucky Derby Odds: 2/5

Preakness Odds: 3/20

Belmont Odds: 1/20

Of all his racing accomplishments, one of the most amazing things about Count Fleet was a work he turned in as a 2-year-old. J. Keeler Johnson wrote a beautiful depiction of the sixth Triple Crown 2inner for America’s Best Racing in February 2018, where he offers an excuse for Fleet’s loss in the 1942 Futurity on a stiff morning work of 1:08 and 1/5th for 6 furlongs shortly before the race.

It’s doubtful many horses had ever gone sub 1:09 in actual races back then and here is a 2 year-old working track records in the morning. Yeah, that might have starched him, but damn did he start clubbing them after that loss.

As a 3 year-old he won the Wood, Derby, Preakness, Withers and Belmont en route to a Justify-esque 6-for-6 perfect record. Of course, Count Fleet ran 15 times at age 2, winning 10 races as a juvenile, four of them stakes races with two track records.

His run through the Triple Crown was absurd in its dominance with the 1943 Belmont Stakes being the single greatest performance by a race horse (until 1973 anyway). The official margin of victory for Count Fleet’s Belmont Stakes was 25 lengths, and the final clocking of 2:28 1/5 was a stakes record. He emerged with an ankle injury and never raced again but his legacy was already cemented.

3. Seattle Slew | 1977

Kentucky Derby Odds:1/2

Preakness Odds: 2/5

Belmont Odds: 2/5

Seattle Slew was racing’s biggest rockstar of the 70s. In 15 of his 17 career starts Slew went to the post as the odds-on favorite. “Slewmania” was in full effect throughout his career as fans would pack grandstands just to see him gallop in the mornings.

He began 1977 with a track record at Hialeah, swept through the Triple Crown as if it were a forgone conclusion and was crowned Horse of The Year. Still, the numbers and times and records and tales do no justice to actually watching this horse run.

His Derby was ridiculous as he missed the break and had to charge through the field to get on the pace before they went under the wire for the first time. His wins in all three races were so easy, so measured, that they left no doubt that his superiority was far greater than the merely his margins of victory.

In 1978 he faced off against Affirmed in the Marlboro Cup in the first ever meeting of Triple Crown winners and asserted his dominance once again winning by an easy three lengths.

2. Citation | 1948

Kentucky Derby Odds: 2/5

Preakness Odds: 1/10

Belmont Odds: 1/5

There are fewer and fewer of them around anymore, but every once in a while you’ll run into an old-timer at the racetrack who will tell you that the greatest racehorse they ever saw was Citation. As the fourth Triple Crown winner of the 1940s, you’d think the sporting public would be getting somewhat blasé to the accomplishment.

But along came Citation to turn the racing world on its head with a run of greatness that still stands throughout all eras of the sport.

There is absolutely no question that his 3-year-old year is the greatest sophomore campaign in the history of racing. He won 19 of 20 races in 1948. His Triple Crown victories came during his record 16-race win streak. During that run he won from distances of 6 furlongs to 16 furlongs (two miles).

He seemingly never broke a sweat during any of the Triple Crown races and he threw in and 11-length score in the Jersey Stakes between the Preakness and Belmont just for good measure. His Belmont victory was more coronation than competition as he flew home to an 8-length victory while equaling Count Fleet’s track record. It was domination to the point of absurdity and jockey Eddie Arcaro was adamant that Citation was the greatest race horse ever.

1. Secretariat | 1973

Kentucky Derby Odds: 3/2

Preakness Odds: 1/2

Belmont Odds: 1/10

What can we say about Big Red that hasn’t been said already? He was the greatest of all-time and his Belmont Stakes victory is the most indelible image in racing. A 31-length margin of victory and world record by more than two seconds, his crowning moment for the Triple Crown is usually the first race people think of when they mention Secretariat, and rightfully so.

The only shame in this is that it completely overshadows a Preakness performance that would have been talked about for years under any other circumstances. He came out of the gates in Baltimore dead last and was 6 lengths back in the first 1/8th of a mile. Ron Turcotte took him wide and looped the entire field in the turn, grabbing the lead before they even straightened out on the backstretch. It’s bewildering to watch.

A move like that at that stage of the race is ill-advised as almost any other horse would have been completely empty by the time they turned for home. But not Big Red. He methodically put Swaps away (again) and marched home to victory like he’d been walking the dog.