The Greatest Kentucky Derbies Ever

The Kentucky Derby is an incredible race, one that can start a horse's Triple Crown candidacy. While it isn't possible to win the Triple Crown on Derby day, it is possible to lose it on Derby day. The goal is to win the race just to have a chance to move to the next leg and be one step closer to the Crown. The following derbies, in particular, were noteworthy for a number of reasons, with some featuring amazing upsets and others featuring great finishes that make them the best Kentucky Derbies ever.

Giacomo, 2005

When you think of horse racing greats, the name Giacomo hardly ever comes to mind. And that is understandable, as Giacomo hardly had a career worth noting during its time on the track. In fact, heading into the 2005 Kentucky Derby, the underdog only managed one win in his seven career starts. And with the way he had raced in the past, nobody expected him to make the Derby win number two of his career. As a result, Giacomo was put at somewhere in the neighborhood of +5000 odds to win the race.

But win the race he did, thanks to a field that wasn't the strongest in Derby history. With Afleet Alex serving as one of the main favorites for the race, this wasn't a Triple Crown campaign that produced any convincing contenders even before the first race had started. Giacomo was able to take advantage of that by just staying alive in the race until the final stretch, where he made his final passes and was able to go down in Derby history as one of the best longshots ever.

Mine That Bird, 2009

In another upset that was up around 50/1 odds, Mine That Bird managed to get the job done in the 2009 Kentucky Derby. This race was an absolute masterpiece by jockey Calvin Borel, who along with Mine That Bird had to overcome a ton of adversity to get the win in the run for the roses. Mine That Bird started this race out in last place in the field of 19 horses, and looked like a horse that had no shot to get the victory. But once it started weaving through competitors, it had turned around the deficit in a hurry.

Mine That Bird managed to win the Derby by over six lengths, going from worst to an emphatic first all within the span of a couple of minutes. It was one of the great comeback stories in the history of the race, and one that won't soon be forgotten in Kentucky Derby lore. Unfortunately, Mine That Bird couldn't keep its Triple Crown bid going, losing in the Preakness Stakes to Rachel Alexandra by one length.

Iron Liege, 1957

Back in the 1950s, the Kentucky Derby was something of a different spectacle. Instead of horse racing fans wearing elaborate hats and drinking mint juleps ironically or as a part of the Derby's pageantry, fans back then wore those hats and had those drinks as a part of their regular lives. More importantly, the 1950s were also a time where premature celebrations were a concern in the horse racing game. In this great Kentucky Derby, it was a premature celebration that stirred the pot and caused one of the most memorable finishes possible.

Gallant Man was leading the Kentucky Derby late, with Bill Shoemaker atop the horse as it tried to close things out. But Shoemaker, excited to be ahead in such a massive race, stood up to celebrate what he thought was a win before his horse had actually crossed the finish line. Gallant Man slowed down, and Iron Liege was able to pass him to win the Kentucky Derby in one of the great gaffes in the history of the sport.

What was so perplexing about this was the fact that Gallant Man and Iron Liege were really battling it out for the win when Shoemaker started celebrating. It wasn't like Shoemaker had lengths on the second place horse at the time. That lends credence to the theory that Shoemaker simply lost track of where the finishing line was, and that he incorrectly thought he had crossed it.

Grindstone, 1996

A photo finish in horse racing isn't completely rare, but also isn't common to where it is an exciting novelty when it does happen. When it happens in a Triple Crown race, though, nerves can go through the roof in anticipation of finding out who actually won such a huge race. That was the case in 1996, when the Kentucky Derby came down to a photo finish between Grindstone and Cavonnier. Cavonnier, who was Bob Baffert trained, had the late lead before being caught by Grindstone. The race was deemed too close to call, and the photographs were consulted.

The delay in finding out who the winner went on for what felt like a lifetime. And at an estimated five minutes or so, it was something of an eternity by the standards of a photo finish. But that was a testament to how close the race was more than anything. In the end, it was determined that Grindstone was the victor, and a Derby that could not have possibly been closer was claimed.

Grindstone's story ended in something of a tragedy, as the horse had to retire shortly after this race due to injury, never having a chance to complete a Triple Crown bid.

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