Kentucky Derby 145: My Picks

May 3, 2019

The field for the 145th Kentucky Derby is set and as always all eyes of the sports world will be on Louisville, Kentucky for the first Saturday afternoon in May for the annual Run for the Roses.

As I’ve written about plenty already, the Kentucky Derby is a must-attend event. Whether you’re fortunate enough to make it to Churchill Downs or you’re having your own Derby party, it is a very festive day around the Bluegrass State and beyond.

Wagering on the race always makes it fun. For some of you beginners, here is a helpful list of some horse racing betting basics to help get you started.

The original favorite, The #12 Omaha Beach, was scratched earlier in the week. That has set the stage for a very entertaining race. On Friday, the #11 Haikal was also scratched.

If you choose to bet some exotics wagers (Exacta, Trifecta, Superfecta etc.), this is the day to do it as the prices are generally high given the fact the field is as large as you’ll see with 20 horses (now 19 horses after scratches) breaking from the starting gate.

There are easily 8-10  horses in this field which have a legitimate chance to win this race. With so many horses breaking from the gate, anything can happen. Things have to break right for your horse to cross the finish line first more so than any other race. In recent years, we’ve seen a very fast pace in the race and that leads me to believe that the winning horse will be one of those that stays just off the pace.

Weather has been a factor recently in five of the last 10 races have been on sloppy tracks. Rain is in the forecast again this year. Hopefully the race won’t be impacted much, but it is something you’ll want to keep your eyes on.

Here’s a look at the horses that pop out to me in the field:

#7 Maximum Security: I always roll out the Florida Derby winner somewhere near the top and have done so for decades as it has proven profitable. In recent years no prep race has yielded more Kentucky Derby winners – Monarchos (2001), Barbaro (2006), Big Brown (2008), Orb (2013), Nyquist (2016), and Always Dreaming (2017). This colt won going away in this year’s Florida Derby and if he gets out well he will make a strong run at the Winner’s Circle again here.

#8 Tactitus: Showed me some grit with his rally in the Wood Memorial after a very fast pace was set. This horse has what it takes to bang up against others and win in a large-field race like this.

#16 Game Winner: My favorite of the Baffert horses. Two wide turns led to a second-place finish to Roadster. This horse can handle the roughness of a 20-horse field. With Omaha Beach scratched, he has emerged as the new betting favorite.

#3 By My Standards: A late riser after coming off an impressive Louisiana Derby and has been training very well. Definitely worth consideration on the outer layer of your bets and a value pick that can win the race outright.

#5 Improbable: The only three of the Bob Baffert horses to draw a post inside the main gate. His final work was terrific and is going back to no blinkers in this one. He ran strong in the mud during the Arkansas Derby and would get a boost if Mother Nature enters the picture.

#6 Vekoma: Bluegrass Stakes winner and nice value pick. Definitely include in your exotics.

#14 Win Win Win: This horse is battle tested and has gone under the radar a bit. His resume indicates he would benefit from a sloppy track too if that becomes an issue.

#17 Roadster: Has to be in consideration, but I’ll be fading more than most. The 17 post is 0 for 40 in Derby history.

#2 Tax
#13 Code of Honor

#1 War of Will
#4 Gray Magician
#9 Plus Que Parfait
#10 Cutting Humor
#15 Master Fencer
#18 Long Range Teddy
#19 Spinoff
#20 Country House
#21 Bodexpress

I like doing a Tri-Wheel each year that keys a few horses on top with about half the field on the bottom in third place.

I have posted this Tri-wheel on every year since I launched the website in 2003. It has hit five times in those 16 years, including in twice in the last four years. During that span the average $1 Tri paid $6,875.67. My two best hits came in 2003 (Funny Cide) and 2010 (Super Saver).

In addition to my Tri wheel, I’ve picked the winner eight times in 16 years and had the exacta seven times as well. Let’s see if we can add to the winnings in 2019.

Here are my picks:

$10 WP – #7 Maximum Security (total $20)

$2 EX Box – #3, #7, #8, #16 (total $24 – you can drop to $1 EX box and only pay $12 for bet)

$1 Tri Wheel
(total $120 – you can drop to down to $0.50 Tri wheel and only pay $60)
#7 Maximum Security / #8 Tacitus / #16 Game Winner with …

#3 By My Standards / #7 Maximum Security / #8 Tacitus / #14 Win Win Win / #16 Game Winner / #17 Roadster with…

#2 Tax / #3 By My Standards / #5 Improbable / #6 Vekoma / #7 Maximum Security / #8 Tacitus / #13 Code of Honor / #14 Win Win Win / #16 Game Winner / #17 Roadster.


Here is a look a the complete field (from

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