Kentucky Derby preview: The year No. 17 is finally No. 1

Betting a Trifecta? Below are the trio of horses that I believe will finish first, second and third at the Kentucky Derby.

WIN: No. 17 Highly Motivated

Not only has the No. 17 spot never produced a Kentucky Derby winner, but Highly Motivated’s trainer Chad Brown has also never been victorious in the Derby either. And 43-year-old jockey Javier Castellano? Zero Derby wins in his career.

So what gives?

One could assume Highly Motivated would be the favorite coming into Churchill Downs had his nose finished first at the Bluegrass Stakes and not Essential Quality’s. Highly Motivated really should have gotten there as he was inside doing all the work, but maybe all of the heavy lifting he had to do in that race may have cost him in the end.

The bottom line: Sometimes horses just lose. Not this time though.

Based on the effort and how he’s progressed entering this race, Highly Motivated deserves to be the buzz horse this week.

His workouts have just been tremendous, and he’s coming off of great speed numbers in three straight races. Never seeing a winner out of the 17 spots is an anomaly, and Javier should be able to look inside at the other speed horses, gradually cut over and save ground, and eventually win the Kentucky Derby.

PLACE: No. 14 Essential Quality

There are so many things to like about this horse: He’s won all five of his career races; Mattress Mack will be betting $3-4 million on him, and he’s had excellent workouts leading up to the Derby.

It’s hard to find faults and easy to like the progression of his numbers as they get better every trip. You have to love Tapit as his sire. Luis Saez seems to fit this horse perfectly.

A little less than a month later, however, I believe that it will be Highly Motivated necking out a win over the No. 14, a great horse but in my opinion not on the level of recent Triple Crown champions American Pharoah or Justified.

The biggest reason not to bet this horse to win? The odds. In a field of 20 horses, 2-1 just does not offer enough value when the horse is not a convincing favorite.

SHOW: No. 15 Rock Your World

Another undefeated horse that is coming in with a lot of buzz.

This is a quality horse that checks a lot of boxes and could figure in the early pace. Rock Your World won’t need the lead, as he can relax off of a horse if one goes ahead of him.

Joel Rosario is a tremendous rider particularly in big races, and the horse’s speed figures are just as good as Essential Quality’s. You don’t get purchased at Keeneland for $650K if you’re a slowpoke after all.

There are a ton of positives here and Rock Your World has a tremendous chance, but is regression possibly coming? All three of his career victories have been at Santa Anita, and I probably would have liked to see him workout more at Churchill Downs ahead of the Derby. The Santa Anita Derby victory was impressive, but he was basically untouched.

Is he experienced enough to win? Probably, but I believe the two aforementioned are more battle tested for the mile and a quarter.

Will you have some exotics and superfecta tickets? Here are some dark horse candidates to consider betting:

No. 10 Midnight Bourbon

Steve Asmussen is still seeking his first Kentucky Derby victory, while jockey Mike Smith is a two time Kentucky Derby winner who fits the horse very well. But is Midnight Bourbon talented enough to actually win?

There is a lot of talent in the field, and pace will be an important factor. His workouts have been really solid coming into the race, and he has spent a lot of time familiarizing the track at Churchill Downs.

Asmussen knows what to do with these big money horses, and Midnight Bourbon seems to have everything going for him on paper.

The question is: What does he do in the biggest race of his career? Midnight Bourbon probably won’t win, but he’ll stalk the pace enough to possibly catch a third or fourth finish.

#8 Medina Spirit

You can never count out a Bob Baffert horse.

But it does feel like a weird horse for Baffert, as the legendary trainer normally looks for horses that are 10 times as expensive as Medina Spirit was.

Baffert will have this horse ready to give full effort, even if he did not finish strong in the Santa Anita Derby. The speed figures are there, and John Velazquez is the rider you would want in any situation.

One concern is that Medina Spirit had some professional runs early on in his career, and it’s questionable whether he’s capable of a big step forward.

He has won two races though and could have some of the best statistical numbers in the field, so he definitely should be considered for tris and supers.

No. 1 Known Agenda

Trainer Todd Pletcher may have started “weeping openly” upon hearing the No. 1 post position, but maybe he wasn’t aware that eight horses have won from the one post in Kentucky Derby history.

Known Agenda isn’t considered a dark horse with his odds, especially after a Florida Derby victory where he dusted the competition. That being said, his closing numbers weren’t that great and sometimes he does quirky things that maybe he’s working through.

He’s got one of the top riders in the country (Irad Ortiz) in one of the top barns in America.

He can’t get banged around too much, and I expect him to stalk while getting close. The price is decent, and Pletcher has won the Derby twice, which should be enough to consider for your tickets.