Kentucky Derby

The 5 Best Kentucky Derby Winners of the 2000s

Christine Aplin

So many great memories came back to life when making a list that, by the time it was done, this became my favorite article of all-time. I’m sure there will be plenty of debate over this list, so let me take a second to mention the horses that I almost included: Big Brown, War Emblem, Funny Cide, and Street Sense all were all horses that I strongly considered putting on the list. Feel free to comment with your personal Top 5 as we take a look back at some of the greatest runnings of this race before what is sure to be another memorable one this Saturday!

Kentucky Derby Wagering Guide

1. American Pharoah (2015)

I don’t want to hear any debate about this one. American Pharoah blazed a path through history, becoming the first Triple Crown winner in 37 years and winning the Breeders Cup Classic to finish his career. He turned what was merely a legend to my generation into a reality. Looking back now, he won the Kentucky Derby without even running his best race. That’s something not to be overlooked.

2. Smarty Jones (2004)

He was “America’s Horse,” with an owner you wanted to root for and an underdog story that everyone could get behind. He was fantastic winning the Kentucky Derby and even better in the Preakness two weeks later. He ran a winning race in the Belmont but was caught late by Birdstone, who was primed and ready for a big effort. The Belmont was the only loss of his career, but sadly, that was also the last race he entered, as injury struck and ended his career.

3. California Chrome (2014)

I’m shocked that it’s turned out this way, but let’s face it, this horse deserves a tremendous amount of credit. I didn’t believe that he was all that great then, and I was still skeptical through his 4-year-old year but that’s not the case anymore. California Chrome became a legend in our sport, and his loyal following rivaled any horse in the past 20 years. If not for Arrogate, he would have won the Breeders’ Cup Classic in 2016 and ended his career as the richest horse in North American history.

4. I’ll Have Another (2012)

If only he’d stayed healthy, he would’ve been the 12th Triple Crown Winner in history. Instead, injury forced him to retire just days before the Belmont. We’ll never know what would’ve happened, but his accomplishments are enough to land him here. He’s the first and only horse to have won the Derby from the 19 hole, and in the Preakness, he managed to run down a loose-on-the-lead Bodemeister, which is still one of the best performances I’ve ever seen.

5. Barbaro (2006)

Going into what was labeled a “wide-open” Derby, the undefeated Barbaro took the lead on the turn and won by six and a half lengths. His stylish win had the racing world raving about what could happen next, but sadly, it all ended in the Preakness when he fractured three bones in his right hind leg. Complications with the injury eventually cost him his life, leaving us to wonder what might have been.

Kentucky Derby Bonus: Access our Top 10 Kentucky Derby Wagering Mistakes for a step-by-step guide on how we’ve hit three straight Kentucky Derby winners.

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