It was two years ago that I sat in the grandstand at Kentucky Derby and tried, like the other 150,000 people there, to figure out what the heck had just happened. Mine That Bird, a 51/1 longshot, had just stunned the world by making an impossible move to take the biggest race there is. Anyone who tells you they knew it was going to happen is lying to you. That was the second highest price horse ever to win the Derby, and the highest since 1913.

Longshot winners aren’t nearly as uncommon as you would think, though. Giacomo won in 2005 at 50/1. In 1999 Charismatic not only won the Derby at 31/1 but came very close to winning the Triple Crown. The field this year is certainly not top-heavy — there isn’t a horse in that field that should intimidate the rest of the runners — so it’s a very good year to be looking at the longshots to see if another miracle can happen. Here are four longer shots that are all fairly interesting:

Twice The Appeal — You have to consider any horse that has Calvin Borel on him — he has won the race three times in the last four years, after all. Borel likes to come from behind, and this horse seems happy to set off a faster pace and then make a late move. Borel hasn’t been on the horse, but he should be suited to him. This horse also came out of the same prep race that Mine That Bird did, though he won the Sunland Derby while the Bird disappointed in his outing.

The most obvious concern with this guy is that he is by a sprinting sire. He looks like he has the capability to run a long way, though, and he’s a proven runner on dirt. Astrology, the horse that was second in the Sunland, came back and ran a nice second in a pretty good Jerome, so that makes this horse look better as well.

Borel’s presence will see him bet down more than he otherwise would be, but even then he’s worth a look as long as he stays at 20/1 or better.

Twinspired — If you have read things I have written about horse racing in the past then you know that I think that synthetic surfaces are one of man’s worst innovations of all times. Just terrible and wrong. To pick a horse that seems clearly to be a synthetic specialist, then, means that something stands out for me. It’s the second place finish in the Blue Grass that does it for me. Now, that was a pretty underwhelming field, but it was one that was absolutely packed with closers. In the face of that this horse was on the pace the whole way, made a bold move forward at the top of the stretch, and missed out by just a nose. On a track that wasn’t set up for a front-running effort and with a whole cavalry trying to chase him down that was an impressive performance. The fact that he not only pushed a pretty solid pace but stayed at the end makes me think he could have more in the tank as the distances stretch out.

The problem, though, is that he has only run on dirt once, and it was ugly. That means the price will have to be right for me to take a risk here. If he can handle the dirt, though, then the front will be a good place for him to be in this race as it sets up.

Animal Kingdom — Normally I am all about dirt prep races for the Derby, but despite a shocking absence of dirt I am intrigued by this guy. He is regally bred, but bred to be a turf horse. While that transition is a tough one, the breeding means he’ll be able to run forever, so the distance is far from a concern.

In this race just getting the distance puts him ahead of much of the field — especially this year. His first time on dirt was a work last week, so that’s a concern, but he seemed quite comfortable. His trainer, Graham Motion, also seems to have forgotten how to lose a race these days, so that helps. You show me a price of 25/1 or better and I’ll show you my cash.

Santiva — Churchill Downs is a surprisingly tricky track given that it seems straightforward, so one of my favorite angles in the Derby is a horse that has had success in the past on the track. Santiva fits that bill very nicely — he won the Kentucky Jockey Club last year and looked very good doing it. He’ll be largely ignored this year, though, because his last race was a horrific ninth-place showing in the Blue Grass. I’m willing to give him a full mulligan for that one, though — he is clearly much better on dirt than synthetics, and he found himself in some real trouble on the rail as well. If he can find some comfort being back on this track then he’ll deliver solid value provided he goes off at about 30/1 or better.

Doc’s Sports expert Kentucky Derby handicappers will have a full card of Kentucky Derby picks for the Run for the Roses on May 7. Doc’s has been putting in extra work this year handicapping the Kentucky Derby field and we expect a big payday on Saturday. Get all Doc’s Kentucky Derby predictions for just $20! Click Here to purchase.