The 5 Worst Derby Winners of the 2000s

Yesterday, we listed the five best Kentucky Derby winners of the 2000s. Today, let’s look at the worst. It’s hard to make a list like this because they did win the biggest race in the country, but we all know that a not-so-worthy horse will sometimes win a race. I had an easy time with the first four horses on the list, but the fifth was a bit of a debate. Let’s take a look at these less-than-desirable Kentucky Derby winners of the 2000s, then leave us a comment with your own list.

1. Super Saver (2010)

He’s an easy choice to top the list because he didn’t have the greatest resume coming into the race and was a complete non-factor after. Super Saver raced three more times after the Derby, finishing eighth, fourth, and tenth. If not for the rain that day, would Super Saver win the Kentucky Derby? Probably not. The good news is that he won the biggest race in America. The bad news is that he’s mostly forgotten.

2. Mine That Bird (2009)

This Derby was one of my all-time favorites because Mine That Bird produced one of the biggest upsets in Derby history. He was so far under the radar that literally nobody knew who was flying past his rivals in an unbelievable last-to-first move. I can remember watching the race and uttering to myself, “Who the hell is the 8 horse?” Unfortunately, though he finished second in the Preakness and third in the Belmont, the Derby was the last win of his career. What happened after that is better off forgotten: he ran seven more times but only hit the board once.

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.

3. Giacomo (2005)

Only a maiden winner entering the Derby, he pulled off a massive upset to win. However, much like his record before the Derby, his performances after weren’t quite up to the elite level, either. He won only once more, the Grade 2 San Diego Handicap at Del Mar. He finished his career with three wins in sixteen starts.

4. Orb (2013)

“I think he could be the one” were words that many uttered after he splashed home to win in 2013. His breeding seemed right, his record looked good enough, and he had connections that everyone wanted to see win. Turns out, he wasn’t the one at all. He struggled in an off-the-board Preakness effort before finishing third in the Belmont. Following that, he only appeared in twice more: the Travers, finishing third, and the Jockey Club Gold Cup, where we was a well-beaten eighth.

5. Monarchos (2001)

I to feel bad about putting any horse here because, past the first four. I respect the rest of the possibilities. Monarchos had a tremendous resume leading up to the Derby and ran a terrific race to win. However, he never again reached the winner’s circle in what was an injury-shortened career. Perhaps the lead-up to the Derby and the race itself took tolls on him.