2020 Kentucky Oaks: Our Best Bets, Longshot Picks, Exotics (Friday, Sept. 4)

Welcome to Kentucky Derby Weekend. The 146th Run for the Roses won't take place until tomorrow, but there's some incredible racing on Friday, headlined by the Kentucky Oaks.

Most people believe that the Oaks is a two-horse race between Gamine and Swiss Skydiver, but I am going in a different direction.

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New to Horse Racing?

For those of you that might be new to horse racing, the wagering pools are pari-mutuel, which means that, unlike in sports betting, you aren’t trying to beat the house but rather the public at large. The key to long-term success in betting the ponies is being disciplined in identifying value in the pools.

Speed Ratings and Beyer Speed Figures

Speed ratings are relative performance indicators that allow us to compare performances across tracks where not all factors are even. Some tracks might be naturally faster like Gulfstream or Santa Anita, where the surfaces are harder, compared to a track like Belmont or Aqueduct, where the surfaces are generally a bit deeper.

They also account for the condition of the track as most horses will travel slower over softer ground. This means that simply comparing times is ineffective as they need some kind of leveling factor.

That’s what is built into speed ratings and they give a nice, although imperfect indicator of relative performance and ability.

Class Rating

A relative strength index for the field of a specific race. This gives you an idea of the level of the competition the horse was facing, as it can vary wildly from track to track even with the same win conditions.

How often do favorites win in horse racing?

Generally speaking, the favorite in horse racing wins at about a 35% rate but that number varies depending on the number of horses in the field. Armed with that knowledge you might want to just pick the favorites, frequently known as the chalk, but a closer look at the implied odds shows that you’d need average odds of 2-1 or better to break even on “win” bets.

So, in order to profit horseplayers must pick and choose the horses that they feel have a better chance to win than their implied odds, which is known as positive expected value (+EV). Expected value is not unique to horse racing and something that all bettors should get familiar with if they want to succeed.

Race 8

3:05 p.m. ET

The stakes action kicks off with G2 8 Belles for three-year-old fillies going seven furlongs on the main track.

There’s a lot of speed in this race, including the morning-line favorite No. 1 Mundaye Call (6-5). Jockey Florent Geroux is going to have to send her from the rail, which could very well put her in a speed duel with a number of other horses in here. Because of her post position, I’m looking elsewhere.

I landed on No. 5 Sconsin (6-1). She’s the only deep closer in the field and it appears as though she’s going to get the pace she needs. While her Beyer speed figures are solid, she’s going to need to continue to improve here.

In her last two starts, she lost to No. 1 Mundaye Call and No. 7 Four Graces (7-5), respectively. Jockey James Graham will be aboard Sconsin for the fourth time and the two of them have never missed the board. Graham and trainer Gregory Foley have teamed up six times at Churchill this year, winning four.

I did give Four Graces a good look for this race. She has four wins from five starts and is a perfect 2-for-2 over the Churchill main track.

Her outside post position will help her as she won’t have to deal with traffic and will be able to sit just off the pace from a few horses to her inside.

She’s the only graded stakes winner in the field, having won the G3 Dogwood, here at Churchill, and the G3 Beaumont at Keeneland.

Bets: No. 5 to win; 5,7 exacta box

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Race 9

3:40 p.m. ET

The G2 Edgewood is also for three-year-old fillies, this time going a mile over the turf course.

The favorite is No. 3 Sharing (6-5). She has 4 wins, 1 second, and 1 third from 6 career starts and is 1-for-1 over the Churchill grass. After rattling off four consecutive victories trainer Graham Motion sent her across the pond to run in the G1 Coronation Stakes at Royal Ascot where she finished second.

This will be her first start in two and a half months, but that shouldn’t be a problem as Motion wins at a 20% rate when his horse is coming off a 61-180 day layoff and she gets her normal rider, Manny Franco back in the irons. She’s my top pick.

No 2. Hendy Woods (4-1) is going to try and run down Sharing late. She has 3 wins from 4 career starts, but the lone loss was a seventh-place finish against graded stakes company.

It makes me wonder if the waters are too deep for her, but she gets hall of fame rider Johnny Velazquez aboard and I think that he will have her a little closer today, not needing to make up as much ground late.

She had a great workout since her last start, going 4 furlongs in 48 seconds. She’s one to include.

The last horse that I looked at was the one on the rail, No. 1 In Good Spirits (5-1). Jockey Miguel Mena is going to send her from the rail, putting her in the race right away.

She ran a competitive third in the G3 Regret back in June and the cut back in distance should help her here. She’s consistently improved her speed figures and if she can do so again, she can be dangerous. Another one to include.

Bets: 1,2,3 exacta box; Pick 5: 1,2,3/6/2,8/1,4/1,4,5

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Race 10

4:15 p.m. ET

Next up we have the G2 Alysheba for four-year-olds and up, which will be run at a mile and a sixteenth over the main track.

For those of you who have followed along with my picks this year, you know one of the horses that I’ve loved all year long has been No. 6 By My Standards (7-5).

He has 5 wins, 4 seconds, and 1 third from 11 career starts. He’s run second in both of his last two starts, but he ran up against two of the best horses in training in Tom’s d’Etat and Improbable, respectively.

By My Standards gets his usual jockey, Gabriel Saez, back aboard today too. Saez has piloted him to all 5 wins and today should get his 6th in this field.

Trainer Bret Calhoun wins at a 30% clip in graded stakes races and it looks like he has By My Standards ready to go after a bullet four-furlong work, going 46 and ⅕ seconds. He’s my best bet of the day.

Bet: No. 6 to win; Pick 3: 6/2,8/1,4

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Race 11

4:50 p.m. ET

The G1 La Troinenne is for fillies and mares four years old and up and will be run over the main track at a mile and a sixteenth.

We have the favorite all the way to the outside in No. 8 Monomoy Girl (4-5). She’s crossed the wire in front in 9 consecutive races dating back to early 2018. She was DQ’d after drifting in one of those races though.

After missing her entire four-year-old season, she came back after a year-and-a-half to show us all she still had. Her outside post combined with her stalking style should set her up perfectly in here. She’s my top pick.

No. 2 Vexatious (4-1) is the only one who stands a chance against the champ. She’s stepped up in class in her last two starts and has run the best two races of her life. Two back she finished a second to Monomoy Girl after being forced to go 6 wide in the stretch and last time out she extremely game and beat Midnight Bisou by a neck, never letting MB go by, who looked like she had all the momentum.

After the confidence-building win against Midnight Bisou in the G1 Personal Ensign, can she flip the tables on Monomoy Girl here? I have to include her.

Bet: 2,8 exacta box

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Race 12: The Kentucky Oaks

5:45 p.m. ET

The Kentucky Oaks is next up. While it’s only a nine-horse field, we are going to have a great horse race on our hands. These three-year-old fillies will be going a mile and an eighth over the main track.

As I mentioned in the opener, many people are saying this is a two-horse race between No. 5 Gamine (1-1) and No. 1 Swiss Skydiver (8-5).

Gamine is definitely fast, but the biggest question is can she get the distance. She’s only gone two turns once and will be stretching out from seven furlongs in her last start, to nine furlongs today. Trainer Bob Baffert always has his horses ready, but at even money, I’m looking elsewhere.

Swiss Skydiver, on the other hand, is going to have to overcome her rail position and contend with Gamine’s early speed. She ran a game second against the boys in the Blue Grass and has continually improved her Beyer speed figures in each of her three-year-old starts.

She’s proven that she can get the distance after winning the G1 Alabama last time out going a mile and a quarter. Jockey Tyler Gafflione stays aboard for trainer Kenny McPeak. While she’s not my top pick, I am going to be using her.

My top pick is No. 4 Speech (4-1). She has 3 wins, 3 seconds, and 1 third from 7 career starts. She’s coming in off a win in the G1 Ashland where she also posted a career-best 101 Beyer. Gamine is going to set blazing fractions and she’s going to sit in a stalking position off of Gamine and Swiss Skydiver.

Speech will make her move coming off the second turn and should have plenty left in the tank to overtake the two favorites late. I love that Javier Castellano has ridden her twice before, both times to victory, albeit one by disqualification.

Bets: No. 4 to win; 1,4 exacta box

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Race 13

6:20 p.m. ET

We end the Oaks Day card with the G2 Turf Sprint for three-year-olds and up, going five and a half furlongs over the turf.

No. 4 Bound for Nowhere (3-1) is my top pick. He’s going to be involved from the start as he will either be on or just off the pace. In both of his last starts, he had the lead in deep stretch, but both times was nipped at the wire.

He has the highest Beyer at the distance, granted that game over two years ago. Trainer Wesley Ward is exceptional with sprinters winning at 27% and 22% with turf sprints.

I also looked down on the rail at No. 1 Diamond Oops (8-1). He’s trying the turf for only the fourth time and while he doesn’t have a win yet, he’s been training very well over the turf course in his last five works.

His last work, he went four furlongs over the turf in a blazing 45 and ⅘ seconds. He gets one of the top turf riders in Florent Geroux and at a great price he’s one I’m including.

No. 5 Extravagant Kid (7-2) is another one that I’m including. He always finds a way to be in the mix late and he loves this Churchill turf course with 2 wins and 1 second from 3 starts. With the amount of speed in this race, look for jockey Tyler Gafflione to make one run with him and try to mow them down at the wire. Trainer Brendan Walsh and Gafflione have teamed up 46 times at Churchill, winning at a 22% clip.

Bet: 1,4,5 exacta box

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