The Top 5 Worst Derby Winners of the 2000s

Monday, 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 of the year, but we all know that a not-so-worthy horse sometimes win a race. Unfortunately, last year’s winner has made this list, but hopefully, the 2018 winner won’t. 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 have won 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.

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. Always Dreaming (2017)

After his Kentucky Derby triumph, it looked at though Always Dreaming was heading for greatness. The Derby was his fourth straight win, and each of those victories was very impressive. However, things went south in a hurry. He was a no-show in the Preakness and missed the board, then struggled at Saratoga over the summer in both the Grade 2 Jim Dandy Stakes and the Grade 1 Travers Stakes. Following the Travers, he was given the rest of the year off, but the good news is that he’s still in training and is a probable for the Grade 2 Alysheba Stakes this weekend. There’s still time for Always Dreaming to turn things around and get himself off of this list.

5. 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 twice more: the Travers, finishing third, and the Jockey Club Gold Cup, where he was a well-beaten eighth.