Eddie Arcaro: The Only Jockey Who Ruled the Triple Crown Twice!

Let’s take a ride through the life and times of Eddie Arcaro, the man who could make a thousand-pound Thoroughbred dance to his tune and who, for three decades, left the competition eating his dust.

If you’ve ever wondered what it takes to become a legend in the world of horse racing, Arcaro’s story is the blueprint with equal parts grit, talent, and a dash of good old-fashioned stubbornness.

Born George Edward Arcaro on February 19, 1916, in Cincinnati, Ohio, Eddie came into the world a lightweight, just three pounds at birth.

His mother joked he could fit in a cigar box, and, at a full-grown 5’2”, he never exactly towered over anyone. But in the world of jockeys, that’s practically perfect.

The son of Italian immigrants, Arcaro’s early life was anything but glamorous. His father was a struggling taxi driver, and young Eddie left school at 13, swapping textbooks for stable work and exercise rides at the local tracks.

By 16, he’d won his first race at Agua Caliente in Tijuana, Mexico. Not bad for a kid who, just a few years earlier, was mucking out stalls and dreaming of glory. The track itself carried the buzz of a casino, with bettors roaring at every finish, and young Arcaro quickly learned how to thrive under that pressure.

Rising Through the Ranks

Arcaro’s early riding days were as scrappy as they come. He was known for a fiery temper, so much so that in 1942, he earned himself a year-long suspension for unseating a rival jockey in a heated race.

When asked to explain, Arcaro didn’t sugarcoat it: he simply admitted he meant to do it. That year off, though, was a turning point. He learned to harness his competitive fire, turning it into the cool judgment that would define his career.

1941: Whirlaway’s Triple Crown Sweep

Kentucky Derby – May 3, 1941

Whirlaway was talented but quirky. He liked to bolt wide on the turns, making him a handful for any jockey.

But Arcaro, never one to shy away from a challenge, worked with trainer Ben A. Jones to fit Whirlaway with a special single-cup blinker to keep him focused.

On Derby Day, Arcaro let Whirlaway settle at the back of the pack for the first three-quarters of a mile. Then, with the crowd roaring, he unleashed Whirlaway’s famous late kick.

The pair surged past the field, winning by a record eight lengths in 2:01, a Kentucky Derby record at the time.

As the Kansas City Star put it, “The greatest little guy in the whole world tonight in the opinion of nearly 100,000 persons is Arcaro – he rode Whirlaway”.

Preakness Stakes – May 10, 1941

Just a week later, Arcaro and Whirlaway lined up for the Preakness. Once again, Whirlaway lagged behind early and at one point, he was nearly 10 lengths off the lead.

But Arcaro knew exactly when to press the button. Down the backstretch, he swung Whirlaway to the outside and, in a matter of seconds, they zipped past the field.

Whirlaway won by five and a half lengths, making it look easy.

Belmont Stakes – June 7, 1941

By the time the Belmont rolled around, Whirlaway was the heavy favourite. With only three rivals, Arcaro took no chances.

He put Whirlaway on the lead with a mile to go and never looked back, cruising to victory by 2½ lengths in 2:31.

With that, Whirlaway became the fifth Triple Crown winner, and Arcaro had his first sweep of the classics.

1948: Citation’s Triple Crown Domination

Kentucky Derby – May 1, 1948

Citation was a different beast – powerful, consistent, and seemingly unbeatable. The Derby that year was run on a rain-soaked, sloppy track, which many thought would favour Citation’s stablemate, Coaltown.

But Arcaro, cool as ever, let Citation stalk the pace before making his move. He surged past Coaltown and won by 3½ lengths, making it look almost routine.

Preakness Stakes – May 15, 1948

Two weeks later at Pimlico, Citation was the odds-on favourite, so much so that only win bets were allowed.

The race was run on another muddy track, but Arcaro kept Citation under a tight hold, letting him lope along in front.

When the time was right, he let Citation out a notch and they galloped away to win by 5½ lengths, barely breaking a sweat.

Belmont Stakes – June 12, 1948

The Belmont was the final test, and Citation faced seven rivals. He stumbled at the start, but Arcaro didn’t panic.

Citation quickly recovered, took the lead on the far turn, and by the time they hit the stretch, he was five lengths clear.

He crossed the finish line eight lengths ahead, tying the stakes record of 2:28.

With that, Citation became the eighth Triple Crown winner, and Arcaro made history as the only jockey to ride two Triple Crown champions.

The Winning Streak: Triple Crowns and Classic Races

Let’s talk numbers, because Arcaro’s stats are the stuff of legend:

• 4,779 career wins out of 24,092 races
• 549 stakes victories (a record that stood for more than a decade)
• Over $30 million in purse earnings
• Five Kentucky Derby wins (1938, 1941, 1945, 1948, 1952)
• Six Preakness Stakes wins (1941, 1948, 1950, 1951, 1955, 1957)
• Six Belmont Stakes wins (1941, 1942, 1945, 1948, 1952, 1955)
• The only jockey to win the U.S. Triple Crown twice

If you’re keeping score, that’s 17 wins in the American classics, more than any other jockey in history.

He was called “The Master” for good reason, his ability to read a race and time his move was uncanny.

As Arcaro himself put it, it wasn’t just about athleticism; it was about judgment, about capitalising on every small error his opponents made.

The Nashua-Swaps Showdown

Arcaro wasn’t just a winner; he was a showman. In 1955, he found himself in one of racing’s most famous rivalries, riding Nashua against Bill Shoemaker’s Swaps.

Though Nashua lost the Derby, Arcaro came back to win the Preakness and Belmont, then bested Swaps in a $100,000 match race, a moment that had fans buzzing for years.

Later Years

As the years rolled on, Arcaro kept winning, often atop some of the sport’s greatest horses.

He called Citation “the greatest horse I ever rode,” but reserved a special place in his heart for Kelso, Horse of the Year five times, saying, “He could do it all. Sprint, go a distance, run all day”.

Off the track, Arcaro mellowed. He became known for his wit and warmth, a far cry from the hot-headed kid of his early days.

He was generous, too: after winning the 1948 Derby on Citation (a ride he got after the original jockey, Albert Snider, died in an accident), Arcaro split his share of the purse with Snider’s widow.

Retirement and Legacy

Arcaro hung up his silks in 1961, after a final ride at Pimlico. But he didn’t stray far from the sport.

He became a television commentator, wrote a book (I Ride to Win!), invested in businesses, and served as president of the Jockeys’ Guild, advocating for riders’ rights.

He was inducted into the National Museum of Racing and Hall of Fame in 1958 and received the George Woolf Memorial Jockey Award in 1953.

Final Lap: Death and Remembrance

Eddie Arcaro died of liver cancer on November 14, 1997, at the age of 81, surrounded by family in Miami.

His legacy remains unmatched: the only jockey to win two U.S. Triple Crowns, the master of the American classics, and a man who turned a small frame and a big dream into a legendary career.

So next time you hear the thunder of hooves and the roar of the crowd, tip your hat to Eddie Arcaro, the little guy who rode bigger than anyone else.

Whether he was switching his whip mid-race or cracking a joke in the paddock, Arcaro was always in control, always a step ahead, and always, unmistakably, “The Master”.

Because in the end, Eddie Arcaro didn’t just ride to win. He rode to make history, and he did, every single time he hit the track.