Ten Derby Matchup Prop Predictions

2019 Kentucky Derby, 5/4/19 Ten Matchup Prop Odds Predictions

While winning big on the Kentucky Derby often requires you to hit a tri or superfecta, there is value to be had for bettors when it comes to the matchup prop odds that are released.

Here are 10 Kentucky Derby matchup prop wagers that I like for Saturday’s Triple Crown race from Churchill Downs.

Tacitus (+125) over Game Winner

In this matchup, we’re getting plus odds on a legitimate contender in Tacitus, who I have in my top 3 today. Tacitus enters the Kentucky Derby off two impressive graded stakes wins earlier in the year. He’s also the son of leading sire Tapit and out of a dam in Close Hatches who was the champion older dirt female of 2014. Tacitus is bred to handle the Derby’s 1 ¼-mile distance and I believe he can hold off a late charge from Game Winner.

Improbable (-135) over Tacitus

While I do like Tacitus to finish in the top-3, if you click the link above you’ll see that I have Improbable winning in my official predictions. Improbable finished second in both of his races this year, but lost by a length to Omaha Beach in the Arkansas Derby. Two things on the Arkansas Derby: One, Improbable wore blinders in that race and didn’t react well, which is why Bob Baffert is ditching the blinders for the Kentucky Derby. Two, Omaha Beach was scratched earlier in the week so we don’t have to worry about Improbable falling to Omaha Beach twice this year. I like Tacitus, but I see the ultra-tactical Irad Ortiz Jr. positioning Improbable perfectly down the stretch and earning a narrow win today at Churchill Downs.

Improbable (-145) over Maximum Security

I have Maximum Security in my top-3 as well but I could see the Florida Derby winner being out-paced down the stretch. As previously mentioned, I think Ortiz Jr. will have a near-perfect ride today on Improbable so I’m going to maximize their odds as much as possible.

Improbable (+100) over Game Winner

Same thought as above: If I believe Improbable and Tacitus have a good chance of landing in the top 3, I’m going to try to maximize my value on both horses. Game Winner is a tough, gritty horse that was a 2-year-old champion. He’s going to be in the mix but I hate his draw (No. 16). He has a tendency to drift out and if he does so again today, he won’t be able to fight through the traffic to eventually get inside before the final stretch.

Improbable (-140) over Roadster

See above. Roadster is extremely talented but he’ll have a difficult time getting into position from the outside. With Improbable set inside of him, Roadster isn’t a good play today from his No. 17 post position.

Maximum Security (+140) over Game Winner

I’m going to have a lot of exposure in terms of fading Game Winner, who again, I do like but I hated his post draw. Maximum Security cruised to a victory in the Florida Derby and while I don’t think he wins today, I do like him to finish in the top 4. He likes to race on the lead and has had some starts this year where he didn’t look to be tiring. If I’m right about Game Winner becoming undone by his post, then this will be a nice value on Maximum Security getting plus odds.

Maximum Security (-110) over Roadster

Again, this is more about Roadster’s bad post draw than the talent of these horses. One other reason to like Maximum Security this evening: Luis Saez, who was aboard Maximum Security in the Florida Derby and who is one of the best pace jockeys in the game today.

War of Will (-115) over Vekona

War of Will suffered a minor injury, which helps explain his bad start in the Louisiana Derby. War of Will has since checked out fine and prior to his Louisiana Derby mishap, he had won all three of his starts on dirt tracks by a combined 11 ¼ lengths. Vekoma, meanwhile, won The Blue Grass Stakes but is a speed horse and is small. I don’t expect him to fare well in today’s sloppy conditions.

War of Will (-140) over Tax

Tax won the Withers Stakes and finished second to Tacitus in the Wood Memorial but he’s close to the rail and could get pushed back. Yes, War of Will is on the rail, so the same theory applies. But I believe War of Will is the more talented horse and thus, I’m willing to roll the dice that jockey Tyler Gaffalione will get War of Will out front early.

Win Win Win (+105) over By My Standards

By My Standards is getting some buzz as one of the long shots that could make noise today at Churchill Downs. That said, he’s been off since the Louisiana Derby and in that race, War of Will had a poor start that compromised his chances. Win Win Win has also reportedly had some excellent workouts leading up to the Derby and I like the value here getting plus odds.

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