The Top 5 Kentucky Derby Winners of the 2000s

So many great memories came back to life when making this list that, by the time it was done, this became my favorite article of all-time. There will be plenty of debate over this list, so let me take a second to mention that I almost included Big Brown, War Emblem, Funny Cide, and Street Sense. I strongly considered putting each one of those greats on this list. Of course, the major question becomes, will we see a Top 5 type of performance this year? This crop is being discussed as one of the best in recent memory, so seeing something special is certainly in the realm of possibilities. Feel free to comment with your personal Top 5 as we take a look back at some of the greatest runnings of this race!

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 won 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 that you wanted to root for and an underdog story that everyone could get behind. He was fantastic when winning the Kentucky Derby and even better in the Preakness two weeks later when he won by a record 11 1/2 lengths. He also ran a winning race in the Belmont, but he was caught late by Birdstone, a horse that 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 that he entered, as an injury 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 back then, and I was still skeptical throughout 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 could’ve become 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 that 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 6 1/2 lengths. His stylish performance 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.