Expert Predictions on Who Will Win the Kentucky Derby


The 2019 Kentucky Derby is set to get underway on Saturday, May 4th at Churchill Downs. This is a Grade 1 stakes race for three-year-old thoroughbreds, and it’s held annually in Louisville, Kentucky. This is a 1 1/4-mile race that is known in the United States as “The Fastest Two Minutes in Sports” as well as the “Run for the Roses”.

It is the first leg of the Triple Crown, which is followed by the Preakness Stakes and the Belmont Stakes. The Kentucky Derby has been run every year since 1875, making this the 145th running. The attendance at the event ranks first in North America and surpasses that of all the other stakes races, including the Breeders’ Cup.

Because of it’s popularity, the Kentucky Derby draws millions of fans and bettors around the world. I’m going to take a look at the wagering side of it and go through and give my predictions for this year’s race. I provide my Trifecta below, which is picking the 1-2-3 (win, place, show) finishers in the correct order. If you Box these horses together, they can finish 1-2-3 in any order, but it costs more.

**Note – I have picked three of the past seven Kentucky Derby Winners with American Pharaoh (5/2) in 2015, Orb (7/2) in 2013, and I’ll Have Another (12/1) in 2012 with my ‘Win’ selections.  

In 2017, I had Always Dreaming picked to finish 2nd and he won, so we cashed our place wager.  I also noted that I may regret not picking him to win.

In 2018, I hit the Exacta AND the Trifecta with Justify, Good Magic and Audible finishing in 1st, 2nd and 3rd.  I had a 6-7-11 Exacta Box and a 5-6-7-11 Trifecta Box.  A $2 Exacta Box cost $12 and paid $69.60, and a $2 Trifecta Box cost $48 and paid back $282.80.

2019 Kentucky Derby Betting: Win, Place, Show and Exotic Picks

Win: No. 5 Improbable (5/1)

Improbable was undefeated in three starts as a 2-year-old.  Since then he lost by a neck in the Rebel Stakes and by a length to Derby favorite Omaha Beach in the Arkansas Derby.  That effort showed he could go the distance with what was previously the best horse in the field in Omaha Beach.  Now, I believe Improbable is the best horse in the field.

The pedigree is a good one as well.  He is the son of City Zip, a Grade 1-winning sprinter and half brother to 2004 Breeders’ Cup Classic and Horse of the Year Ghostzapper.  It’s also worth mentioning he has the same trainer and owner as Triple Crown winner, Justify.

I like the running style of Improbable.  He likes to stalk the leader and sit no more than one or two lengths behind before making his move around the final turn.  There isn’t going to be a lot of speed in this race, so the stalkers will have the advantage over the closers.  Horses sitting too far off the pace will have no chance.  Improbable has as good a chance as any at winning the Run for the Roses this year.

Place: No. 16 Game Winner (6/1)

Game Winner is basically a nose and a half-length away from being unbeaten with the two losses coming to elite competition.  He lost to Omaha Beach in the Grade II Rebel Stakes by a nose, and we all know that Omaha Beach was the favorite to win the Kentucky Derby before getting scratched.

Then, with his ticket already punched into the Kentucky Derby, Game Winner lost to fellow Bob Baffert trainee Roadster by a half-length in the Grade 1 Santa Anita Derby.  Well, there’s been talk that Game Winner didn’t give it his all in that race because he didn’t need to.  Roadster needed the win to quality for the Kentucky Derby, so it would make sense that Baffert would have instructed the jockey of Game Winner to let Roadster win.

The pedigree is a good one as well for Game Winner, which is a bay colt by Candy Ride, the sire of 2017 Horse of the Year Gun Runner.  He is also out of Indyan Giving, the daughter of A.P. Indy and champion older mare Fleet Indian. Game Winner can get the distance as Fleet Indians scored in the 1 1/4-mile Personal Ensign (G1) and Delaware H. (G2), and her other stakes wins all came at 1 1/8-miles, the most notorious of which was the Beldame (G1).

Show: No. 8 Tacitus (5/1)

Tacitus won both of his Derby prep races with victories in the Grade II Tampa Bay Derby and the Grade II Wood Memorial.  His victory in the Wood Memorial was made even more impressive by the fact that he was bumped at the start, yet he went on to post the best Brisnet speed figure (103) of any horse in their final prep race.

Tacitus has the perfect racing style to win the Kentucky Derby, too.  He likes to sit mid-pack, just behind the first set of stalkers.  He has drawn the 8th post position, and most horses have had success from the 5-10 spots.  He should get a nice trip and be able to stalk the early leaders.

Juddmonte Farms has captured all of the world’s biggest races except the Kentucky Derby.  In Tacitus, they believe they will capture the Run for the Roses this year.  Dam Close Hatches is a thorough Juddmonte product top and bottom.  Sire First Defence is a near relation to homebred Empire Maker, the runner-up as the Derby favorite that went on to win the Belmont.

Exacta Pick: 5, 8, 14, 16 ($2 Exacta Box Costs $24)

Trifecta Pick: 5, 8, 14, 16 ($2 Trifecta Box Costs $48)

Superfecta Pick: 5, 8, 14, 16 ($1 Superfecta Box Costs $24)

Note: I’m throwing in No. 14 Win Win Win (12/1) in my Trifecta Box as I believe he is the horse with the fourth-best chance to hit the board.  Other horses I consider to have a shot in order are Roadster (5/1), Vekoma (15/1), Maximum Security (8/1) and Code of Honor (12/1).

If you are new to the Kentucky Derby, then you might want to check out my betting guide for beginners.  This year’s complete odds are listed below.

Updated Odds to Win the Kentucky Derby (2019)

Odds courtesy of BetOnline

Horse Jockey Trainer Career Earnings Odds Change Kentucky Derby
Game Winner Joel Rosario Bob Baffert $1,810,000 +600 New 11.58%
Improbable Irad Ortiz Jr. Bob Baffert $589,520 +600 New 11.58%
Roadster Florent Geroux Bob Baffert $636,000 +700 New 10.14%
Code of Honor John Velazquez Claude R. McGaughey $432,070 +800 New 9.01%
Maximum Security Luis Saez Jason Servis $582,800 +900 New 8.11%
Tacitus Jose Ortiz William I. Mott $610,000 +1000 New 7.37%
Vekoma Javier Castellano George Weaver $747,600 +1400 New 5.41%
By My Standards Gabriel Saez Bret Calhoun $600,000 +1600 New 4.77%
Tax Junior Alvarado Danny Gargan $307,500 +1600 New 4.77%
War of Will Tyler Gaffalione Mark Casse $450,840 +1600 New 4.77%
Win Win Win Juilen Pimentel Michael Trombetta $316,000 +1800 New 4.27%
Bodexpress Chris Landeros Gustavo Delgado $188,000 +2500 New 3.12%
Country House Flavien Prat William I. Mott $220,000 +3300 New 2.38%
Cutting Humor Corey Lanerie Todd Pletcher $462,467 +3300 New 2.38%
Long Range Toddy Jon Court Steve Asmussen $830,000 +3300 New 2.38%
Plus Que Parfait Ricardo Santana Jr. Brendan Walsh $1,540,400 +3300 New 2.38%
Spinoff Manny Franco Todd Pletcher $224,000 +3300 New 2.38%
Gray Magician Dryden Van Dyke Peter Miller $211,666 +5000 New 1.59%
Master Fencer Julien Leparoux Koichi Tsunoda $168,979 +5000 New 1.59%

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