By Mint Julep

Kentucky Derby Winner Alan-a-dale 1902

kentucky derby winner alan a dale 1902

In the 1902 Kentucky Derby, Alan-a-Dale achieved a thrilling victory with jockey Jimmy Winkfield at the reins. Despite facing lameness during the race, they managed to secure a narrow win by just a nose margin. The event showcased both horse and rider’s resilience and determination in the face of fierce competition from rivals like Inventor and The Rival. This highlighted the excitement and unpredictability that make this iconic horse racing spectacle so special. Following their triumph, Alan-a-Dale’s connections took home a purse of $4,850 – solidifying their place in history as champions of one of America’s most prestigious races.

Kentucky Derby Winner Alan-a-dale 1902

The 1902 Kentucky Derby marked a significant moment, not just for Alan-a-Dale’s win but also because it was the first time the race took place on a Saturday. This change aimed to attract more fans and boost the event’s popularity. The switch turned out well as spectators witnessed an intense competition where Alan-a-Dale faced unexpected lameness during the race, making his victory by a nose even more impressive.

Jockey Jimmy Winkfield played a crucial role in guiding Alan-a-Dale to success despite facing challenges midway through the race. Winkfield showed remarkable resilience and determination, skillfully maneuvering past obstacles to outperform competitors at every corner. Their teamwork under pressure showcased true grit, eventually leading them to triumph against tough odds and securing their spot in Kentucky Derby history.

Among Alan-a-Dale’s rivals were notable horses like Inventor and Lieutenant Gibson who provided strong competition throughout the thrilling race. Despite their best efforts, they couldn’t match Alan-a-Dale’s sheer tenacity and unwavering spirit. Each horse brought unique strengths into play that day, creating an electrifying atmosphere full of surprises until those final moments when Alan-a-Dale claimed victory by a narrow margin.

The 1902 Kentucky Derby didn’t just crown Alan-a-Dale as champion but also distributed substantial prize money among all involved in this exciting display of speed and endurance. With high betting interests during this heated contest between top racers, payouts reflected both risky gamblers’ fortunes and skilled predictions made by seasoned bettors who put their faith in underdogs like Alan-A-dal led by jockeys such as Jimmy Winkfield whose expertise stood out amid fierce competition sparking excitement across Churchill Downs on that unforgettable May day over one hundred years ago!

Jockey Jimmy Winkfield

Jimmy Winkfield’s win on Alan-a-Dale in the 1902 Kentucky Derby shows his incredible talent and resilience. Despite challenges like the horse’s lameness during the race, Winkfield skillfully guided Alan-a-Dale to victory, demonstrating his determination and expertise on the track.

The 1902 Kentucky Derby had tough competition from horses like The Rival who set a fast pace early on. However, it was Jimmy Winkfield’s smart moves that helped him and Alan-a-Dale win this prestigious event.

Winkfield’s historic victory was not just a personal triumph but also a significant moment in racing history as he became the final African American jockey to win at the Kentucky Derby before segregation policies affected professional horse racing.

Back then, winning such a big race came with substantial rewards; first place paid out $4,850—a huge amount by today’s standards. This sizable sum reflected both how prestigious winning was and how intense the competition among riders striving for that top spot could be.

By overcoming obstacles and coming out successful in one of horse racing’s most famous events, Jimmy Winkfield solidified his legacy as an iconic figure whose skills transcended barriers both on and off the racetrack. His tale continues to inspire aspiring jockeys from all generations while remaining engraved in sports history as a shining example of perseverance against all odds.

The Pros & Cons of Jockey Strategies


  1. Using smart jockey tactics can boost how well the horse performs.

  2. They let riders adjust to various track conditions with ease.

  3. Making strategic choices can result in surprising wins.

  4. Jockey strategies demonstrate the rider's talent and know-how.

  5. Well-planned strategies can help a jockey stand out from the competition.


  1. Messing up strategies can lead to races turning out badly.

  2. Being too aggressive with strategies might tire the horse out too early.

  3. Picking the wrong strategy can cause missed chances for success.

  4. Not adjusting strategies for unexpected situations during the race could be a problem.

  5. Relying too much on luck instead of skill in your strategies could end up hurting you.

Winning Horse and Connections

Alan-a-Dale, a spirited chestnut horse with fiery determination in his eyes, raced down the stretch at Churchill Downs surrounded by cheering fans. The exciting race played out as Alan-a-Dale surged ahead by just a nose length, showcasing both his immense power and unwavering spirit.

Jimmy Winkfield’s bond with Alan-a-Dale was truly magical that day; his expert handling guided them through tight spots and challenges on the track. Winkfield’s skilled jockeyship proved vital as he encouraged Alan-a-Dale to push past tough rivals in a thrilling sprint towards victory.

The crowd at the Kentucky Derby erupted into joy as their hearts raced alongside the thundering hooves approaching the finish line. This heart-stopping finish was recorded in history books, immortalizing not only Alan-a-Dale but also Jimmy Winkfield for their remarkable show of skill and perseverance.

Picture McDowell’s excitement as he witnessed his prized possession cross that prestigious finish line first – pride swelling like an untamed river within him! The triumphant trio – owner, jockey, and horse – reveled in glory under the radiant Kentucky sun on that significant Derby day of 1902.

Alongside fame and glory came riches beyond belief: prize money totaling $4,850 awaited these deserving champions. Such rewards were well-earned by those who dared to dream big dreams and chase them across fields where legends gallop freely under wide-open skies.

Race Outcome and Contenders

Amidst the bustling crowd and thundering hooves, Alan-a-Dale surged forward with unwavering determination that left onlookers in awe. It was a historic moment where grit and grace clashed on the racetrack. Jimmy Winkfield’s victory riding Alan-a-Dale symbolized resilience against all odds—a true testament to their skill, endurance, and unwavering spirit.

The Kentucky Derby of 1902 wasn’t just about one standout performer; it was a showcase of talent competing for glory. Inventor’s strong second-place finish highlighted his speed and expertise as he pushed towards the finish line with impressive tenacity. Not far behind was The Rival, displaying sheer willpower by coming within half a length of Inventor—an exciting show of competition that kept spectators on edge throughout the race.

As cheers erupted at Churchill Downs, bets were settled, fortunes were made or lost—such is the excitement and unpredictability synonymous with horse racing. Payouts resonated across the grounds like ripples in water: $4,850 went to Alan-a-Dale’s connections for their triumph while Inventor’s team earned $700 for their admirable performance securing second place. Standing beside them was The Rival’s camp receiving $300—a reminder that even those who come close make an unforgettable mark on this historic event known as “The Run for the Roses.”

Thrilling Finish: Neck-and-Neck Race Results

Finished Post Horse Jockey Trainer Owner Time / behind
1st Alan-a-Dale Jimmy Winkfield Thomas Clay McDowell Thomas Clay McDowell 2:08.75
2nd Inventor Robert "Tiny" Williams T. W. Moore Nose
3rd The Rival Nash Turner Thomas Clay McDowell Thomas Clay McDowell 1/2
4th Abe Frank Monk Coburn Henry McDaniel George C. Bennett & Co. Nose

Payouts and Prize Money

When Alan-a-Dale won the 1902 Kentucky Derby, it not only made him a legend in horse racing but also earned his owner Thomas Clay McDowell and the winning team $4,850. This was a big deal because it showed how skilled and determined Alan-a-Dale was on race day at Churchill Downs.

On the other hand, the second-place finisher got $700, which is good money but still less than what Alan-a-Dale took home. The third-place contender received $300 for their hard work, showing just how tough the competition was among these talented jockeys and horses fighting for victory in one of America’s top races.

The way the prize money was given out highlighted how important Alan-a-Dale’s win was as he beat competitors who had worked really hard for this moment. The money wasn’t just about cash; it also represented respect and recognition gained on that famous racetrack where champions were born and dreams came true.


1. How did Alan-a-Dale and jockey Jimmy Winkfield overcome challenges during the 1902 Kentucky Derby?

In the 1902 Kentucky Derby, Alan-a-Dale and jockey Jimmy Winkfield faced a tough challenge as they started off slowly and had to navigate through a packed field. Despite the obstacles, they showed impressive resilience and skill to claim victory in the race.

2. What made Alan-a-Dale's victory in the 1902 Kentucky Derby so significant in horse racing history?

The 1902 Kentucky Derby win by Alan-a-Dale was a big deal in horse racing history because the winning horse and jockey Jimmy Winkfield showed incredible toughness. They conquered tough conditions and strong competition to make their mark in racing history.

3. Who were some of the notable contenders that Alan-a-Dale faced in the 1902 Kentucky Derby?

Alan-a-Dale competed against tough rivals like The Rival, Inventor, and McChesney in the 1902 Kentucky Derby.

4. What was the prize money distribution and payouts for the 1902 Kentucky Derby, particularly for the winning horse and jockey?

In the 1902 Kentucky Derby, jockey Jimmy Winkfield rode Alan-a-Dale to victory, winning a grand prize of $4,850 from a total purse of $5,100.

5. How did Jimmy Winkfield's skill as a jockey contribute to Alan-a-Dale's success in the 1902 Kentucky Derby?

Jimmy Winkfield's amazing talent as a jockey, along with his smart race-riding skills and strong determination, helped lead Alan-a-Dale to win the 1902 Kentucky Derby.

6. What factors set the 1902 Kentucky Derby apart from other races of its time, making it a memorable event in horse racing history?

The 1902 Kentucky Derby made a mark in horse racing history with Alan-a-Dale's impressive win. Jockey Jimmy Winkfield showed great resilience, and the race was full of competitive spirit despite tough conditions and strong opponents.