The Complete Guide to the 145th Kentucky Derby

By Chad Cooper

Twitter @thechadcooper

A day after the Kentucky Derby post-position draw, favorite Omaha Beach pulled out of the race due to a breathing issue and opens up the betting even more. 

Not only that, meteorologists in Louisville have all predicted wet weather for the 145th running that takes place Saturday, May 4, around 5:50 CST p.m. at Churchill Downs. It also shifts the handicapping focus to find horses that like to run on a muddy track.  

1-War of Will (15-1)

J: Tyler Gaffalione

T: Mark Casse

Holly M. Smith Photography 2019

If the 11 horse Haikal scratches due to a hoof issue, War of Will shifts to the 2-hole, which greatly improves his chances. This colt had won 3 in a row then threw a clunker in the Louisiana Derby finishing a well-beaten 9th as the race favorite. We found out the horse was injury, so he had an excuse. He has a lot of early speed so jockey Tyler Gaggalione will have to get him out of the gate quickly, but I don’t know if the horse is actually fast enough because his biggest Beyer number is 94. War of Will has off-track breeding in his bloodlines and has run in the mud once, which was a dominating Maiden win at Churchill Downs. Use in exotic bets. 

2-Tax (20-1)

J: Junior Alvarado

T: Danny Gargan

Photo: Cal Sport Media via ZUMA Wire

This gelding was claimed for $50K last year and now gets a spot in the Derby. He has been consistent in all five races and has never been worse than 3rd. Tax won the Withers, but against a weak field then came back to finish 2nd behind Tacitus, who is in this race. I love his distance breeding, but if he continues to be slow out of the gate he will be behind a wall of horses. Though he does have off-track breeding, Tax has never run on a wet surface. 

3-By My Standards (15-1)

J: Gabriel Saez

T: Bret Calhoun

Photo:  Eclipse Sportswire

Big 22-1 upset winner in the Louisiana Derby. This colt is being tagged a “Wise Guy” pick, but I have never been big on horses that won the Louisiana Derby. I’ll say this – the horse has never run a bad race and at worst has finished third. His only start on a wet track was a 2nd place finish at Churchill Downs. 

4-Gray Magician (50-1)

J: Drayden Van Dyke

T: Peter Miller

America’s Best Racing

“Bet a gray on a rainy day.” There are two gray horses in this race – this one and the 8-Tacitus. I’m not betting this one. He qualified with a 2nd place finish in the UAE Derby and those horses don’t have a good track record in the Derby. He would have to grab the early lead and go wire-to-wire to win. 

5-Improbable (5-1)

J: Irad Ortiz Jr.

T: Bob Baffert

Improbable winning the Los Alamitos Futurity (gr. I) – © Benoit Photo

This colt, also trained by Baffert, won his first three starts of his career then finished second in his next 2 races to Long Range Toddy (who is also in the Derby) and Omaha Beach. Jockey Jose Ortiz rode Improbable in his last start, but jumped ship to ride Tacitus, so his brother Irad Ortiz gets the call. The colt had trouble in the gate in the Arkansas Derby and still managed to run 2nd. The owners of the horse won the Derby last year with Justified and the last time an owner won consecutive Derbies came in 1972-73. I love the off-track breeding and his late pace numbers, yet something tells me to stay away. But I can’t.   

6-Vekoma (15-1)

J: Javier Castellano

T: George Weaver

Vekoma and jockey Javier Castellano win the Blue Grass Stakes (G2) at Keeneland on April 6, 2019 (c) Coady Photography/Keeneland

Vekoma has won 3 of 4 races and his lone loss came in the Fountain of Youth Stakes where he was beaten by more than 3 lengths by Code of Honor, who also enters the Derby. Hall of Fame jockey Javier Castellano will need to use this colt’s early speed to gain good position around the first turn. The colt has won on 3 different tracks and is bred to run in the mud. Using. 

7-Maximum Security (8-1)

J: Luis Saez

T: Jason Servis

Maximum Security won his fourth start without a defeat in the March 30 Florida Derby under jockey Luis Saez. (Eclipse Sportswire)

Is Maximum Security a freak horse? The colt is undefeated with a perfect 4-4 record, but every race was at Gulfstream Park in Florida. He hasn’t had much competition and has those four races by a combined 37 lengths. The win in the Florida Derby was at a snail’s pace. He has plenty of early speed, but will he have some left in the gas tank? Not a lot of mud breeding, but did romp in the mud at 6 furlongs. The owners of this horse, Gary and Mary West, also own the 16-Game Winner. 

8-Tacitus (8-1)

J: Jose Ortiz

T: Bill Mott

This gray colt comes to Kentucky with a record of 3 wins in 4 starts. Jose Ortiz has been aboard him in each of those races, which included victories in the Wood Memorial and Tampa Bay Derby. I usually love this type of horses – big, strong and closers – but there isn’t a lot of early gas in this year’s race. He has won two Derby prep races and that’s impressive. 

9-Plus Que Parfait (30-1)

J: Ricardo Santana

T: Brendan Walsh

Plus Que Parfait and jockey Jose Ortiz win the UAE Derby on Saturday, March 30, at Meydan Racecourse in Dubai. (Photo: Photo courtesy of Dubai Racing Club)

For starters, don’t like the name of this horse. He won the UAE Derby, but I’m not really impressed with that. He got smoked in the Risen Star in Louisiana and was flat in the LeComte. I do like that 2nd place finish in the slop at Churchill and the fact that he can crash the board at big odds. Not a winner, but will use in my tri & super. 

10-Cutting Humor (30-1)

J: Cory Lanerie

T: Todd Pletcher

Not many times do you see a Todd Pletcher horse at 30-1. He won the Sunland Derby and had some furious fractions in the final furlong of that race. Other than that not much to see here. He’s bred to run on the mud, but I need more. 

11-Haikal (30-1)

J: Rajiv Maragh

T: Kiaran McLaughlin

Getty Images

This colt had an abscess issue this week, so he may not run at all. Solid consistency and good off-track breeding, but he’s never left Aqueduct.  

12-Omaha Beach – SCRATCHED

13-Code of Honor (12-1)

J: John Velazquez

T: Claude McGaughey

March 2, 2019: #1 Code of Honor with jockey John Velazquez on board, wins the Xpressbet Fountain of Youth Stakes GII, on March 2nd, 2019 at Gulfstream Park in Hallandale Beach, Florida. LizLamont/Eclipse Sportswire/CSM

I don’t know what to do with this horse. He won the Fountain of Youth then was beaten by Maximum Security in the Florida Derby. Not a fan of the breeding, but 3rd race off a layoff is enough for me to use in the bottom half of my exotics. 

14-Win Win Win (12-1)

J: Julian Pimentel

T: Michael Trombetta

Another consistent runner. In 6 starts, the colt has never been worse than 3rd. He has no early speed so he needs to come rolling late. He has run behind Vekoma and Tacitus and I think he runs behind them again. Will use in my exotics. 

15-Master Fencer (50-1)

J: Julien Laparoux

T: K. Tsunoda

This colt is the 1st from Japan to qualify for the Derby. The last horse from outside of America to win the Derby came in 1983 with Sunny’s Halo, and he was Canadian. This one needs a miracle.  

16-Game Winner (9-2)

J: Joel Rosario

T: Bob Baffert


Game Winner, a horse running in the 2019 Kentucky Derby, took some time Tuesday to run on the Churchill Downs dirt. April 30, 2019. Matt Stone, Louisville Courier Journal

This colt went undefeated last year as a 2-year-old and was named “2 Year Old Champion” after a dominating win in the Breeders’ Cup Juvenile at Churchill Downs. But his return to the racetrack in 2019 has been consecutive second place finishes – once to Omaha Beach by a nose and half-length loss to Roadster. Should have no trouble on a wet track with fantastic breeding. The last 6 Derbies have been won by the betting favorite and he will likely be the favorite come post time. 

17-Roadster (5-1)

J: Florent Geroux

T: Bob Baffert

LOUISVILLE, KENTUCKY – MAY 01: Roadster runs on the track during morning training for the Kentucky Derby at Churchill Downs on May 1, 2019 in Louisville, Kentucky. (Photo by Andy Lyons/Getty Images)

Roadster is the 2nd of three Bob Baffert-trained runners in the Derby, but will get a new jockey for the first time in his four-race career in Frenchman Florent Giroux, who is looking for his first Derby win. Jockey Mike Smith had been in the saddle all four times for Roadster yet he bailed for Omaha Beach, who has since been scratched. Roadster has never raced out of California so this will be a big test for him. After his only loss, Roadster had minor throat surgery and came back to win his next two. 

18-Long Range Toddy (30-1)

J: Jon Court

T: Steve Asmusssen

This horse beat Improbable in the Rebel Stakes then came back in the Arkansas Derby and finished 14 lengths behind Omaha Beach, Improbable and Country House over a sloppy track. If the track is indeed wet on Saturday, I’ll pass. 

19-Spinoff (30-1)

J: Manuel Franco

T: Todd Pletcher

I like this Todd Pletcher trainee over Cutting Humor. Spin Off was only 4 races under his hooves and has never been worse than 4th. At 30-1, I’m spending some money on him to win and hit the board in the exotics. 

20-Country House (30-1)

J: Flavien Pratt

T: Bill Mott 

This Lookin’ At Lucky colt had a ton of late gas. In the Arkansas Derby, he came from 10th to finish 3rd behind Omaha Beach and Improbable. He will needs early speed to have a chance to win, but I do love his value to hit the board. 

Pick: 5-16-8-19-6-17

Remember one thing when betting the Derby – Scared money don’t make no money!

Bet 1: $10 win: 3, 5, 6, 8, 16, 17, 19 ($70)

Bet 2: .50-cent trifecta: 5,8 with 1,2,3,5,6,7,8,14,16,17,19 with 1,2,3,5,6,7,8,13,14,16,17,19, 20 ($110)

Bet 3: $1 superfecta: 5,8,16 with 5,8,16 with 3,5,6,8,13,14,16,17,19 with 2,3,5,6,8,13,14,16,17,19,20 ($336)

Total bet: $516

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