Magic Man’s preview and picks of Kentucky Oaks 2019

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It is the greatest week of spring in the world of horse racing as the Kentucky Oaks and Kentucky Derby weekend arrives.

Two great days of racing over the fabled twin spires at Churchill Downs start Friday, and The Magic Man is going for three consecutive winning picks in the Kentucky Oaks. This year’s rendition looks like a really wide open one.

Bellafina, the favorite, drew post No. 4 for the Oaks which drew 16 horses. Only 14 will start though.

Most of the pundits feel that Bellafina is going to be too good but the Magic Man has looked at this group of fillies and senses a potential upset. Upset, you say? Ah, my dear readers, you must read further for my intricate wisdom.

When I look at the body work from this field, I sense an opportunity for a big payoff if the right combination of horses hit. Let’s dive deeper into the 145th Kentucky Oaks, horse-by-horse.

Entries: Longines Kentucky Oaks (G1)
Churchill Downs, Friday, May 03, 2019, Race 11
• Grade I
• 1 1/8m
• Dirt
• $1,250,000
• 3 yo Fillies
• 6:12 PM (local)

PP Horse Jockey Wgt Trainer M/L
1 1Out for a Spin (VA)
Irad Ortiz, Jr. 121 Dallas Stewart 15/1
2 2Chocolate Kisses (KY)
Julien R. Leparoux 121 Mark E. Casse 20/1
3 3Lady Apple (KY)
Ricardo Santana, Jr. 121 Steven M. Asmussen 20/1
4 4Bellafina (KY)
Flavien Prat 121 Simon Callaghan 2/1
5 5Flor de La Mar (KY)
Joel Rosario 121 Bob Baffert 20/1
6 6Positive Spirit (KY)
Manuel Franco 121 Rodolphe Brisset 30/1
7 7Jaywalk (KY)
Javier Castellano 121 John C. Servis 8/1
8 8Motion Emotion (KY)
Mike E. Smith 121 Thomas L. Van Berg 15/1
9 9Liora (KY)
Channing Hill 121 Wayne M. Catalano 20/1
10 10Champagne Anyone (KY)
Chris Landeros 121 Ian R. Wilkes 6/1
11 11Jeltrin (KY)
Luis Saez 121 Alexis Delgado 15/1
12 12Street Band (KY)
Sophie Doyle 121 J. Larry Jones 15/1
13 13Serengeti Empress (KY)
Jose L. Ortiz 121 Thomas M. Amoss 8/1
14 14Restless Rider (KY)
Brian Joseph Hernandez, Jr. 121 Kenneth G. McPeek 6/1
15 15Dunbar Road (KY)
Jose L. Ortiz 121 Chad C. Brown 5/1
16 16Point of Honor (KY)
John R. Velazquez 121 George Weaver 20/1


1-Out for a Spin

There is an old saying in horse racing — If you did not go to the wedding, why go to the reception? This filly shocked in the Ashland at odds of 52-1 as she won by a desperate neck over Restless Rider who is also slated to run but drew the 14 post. Everything points to a colossal regression here but there are two things to consider. First off, her trainer Dallas Stewart is known for pulling surprises in this race (i.e. Lemons Forever in 2006 at 47-1). Also, Irad Ortiz is an absolutely terrific rider aboard ‘Spin here. Assessing her chances, I am going to stick to the rules of racing when horses run as big as she did. There is just no way she can reproduce that effort. Compounding that she draws the rail. Ask yourself how much did that Ashland take out of her? Begrudgingly I will eliminate her.

2-Chocolate Kisses

As I mentioned before my preview, I am going to try and beat the favorite Bellafina. This filly provides a very tempting option. Two starts back she debuted on dirt aand took advantage of a blistering pace to win the Honeybee at Oaklawn. This filly was then compromised by a slow pace in her most recent out in the Ashland when she laid much closer than usual to the early speed; that seemed to take away her kick but she managed to finish third that day. With what appears to be a plethora of early speed in the Oaks, I expect this filly to lay back and revert to to what suited her in the Honeybee. If she can work out a trip without any hindrance, this filly could at the least crash the gimmicks and maybe even win this. Is she my pick? Stay tuned.

3-Lady Apple

This filly is really coming to hand as evidenced by her recent win in the Fantasy at Oaklawn Park. It was a decisive win over an outmatched field. When I look at her speed figures, this Lady appears to be a rung below the main body of contenders in the Oaks. Her trainer Steve Asmussen has won this race twice so he knows how to get his charges ready. I think this filly can be used in trifectas and superfectas but I am not bullish on her chances to win this Oaks. It just appears there are others here better than her.


The early morning line favorite for this Kentucky Oaks comes in off a sterling effort in the Santa Anita Oaks. To most pundits the race is hers to lose. While in theory that may be correct, I by no means feel she is a slam dunk. Remember, she shipped here to run in the Breeders Cup Juvenile Fillies in which she ran fourth. I have questions about whether she can ship from her home base in California and be as effective. Her rider Flavien Prat was aboard the Oaks favorite Paradise Woods two years ago and inexplicably got caught up in a ridiculous speed duel. You would think Prat learned from his misdeeds that day but I just don’t know about this filly anyway. I’d be completely foolish to knock her out of my gimmicks but I am definitely going to find a viable alternative for the win.

5-Fkor de la Mar

This filly was a distant second to Bellafina in the Santa Anita Oaks but she was only making her third lifetime start that day. She has an absolute right to take a step forward. It was her first try around two turns. Bob Baffert is her trainer, and we know he rarely sends 20-1 shots in a race of this magnitude unless he feels she can compete. This filly will sit off of what is expected to be a hot pace. She just needs a clean trip. The obvious question is, will she be good enough in what will easily be her toughest test? I found an opportunity like this one just two years ago when Abel Tasman trained by Baffert got up at 9-1 to win the Oaks. There is a chance this race will be run on an off track and who knows maybe lightning can strike twice? She is in the mix for exotics.

6-Positive Spirit

The one positive you see with this filly is her consistency as she is as honest as can be. I feel these waters are way too deep though. She would have to make a quantum leap to even contend in the stretch. Plus, she will be a part of a grueling pace in which there are better speed types. All-in-all she is a throw out for me.


The combination that brought you Cathryn Sophia in 2016 to win the Kentucky Oaks are here with the reigning Juvenile Fillies Champion who will be making the all important third start off the layoff.In her two races thus far this year, she was unable to close the deal in either the Davona Dale Stakes at Gulfstream or the Ashland at Keeneland. She has burned a lot of money of the wagering public yet she sits at 8-1 on the morning line. If you are still a believer in her, you will get sweet odds this time. She did have her best race over this strip when she won the Breeders Cup Juvenile Fillies but she is a pacesetter who will not be allowed an uncontested lead. I do not think she will disgrace herself but the expected hot pace may do her in. She has the credentials to run big but there are too many questions for me to give her a ringing endorsement.

8-Motion Emotion-Another one who could make an early impact and she has run well this year. Saying that she faded in both the Honeybee and Fantasy Stakes at Oaklawn. I don’t think stamina is on her side and she figures to fade out of the proceedings when the chips are down.So she is a toss for me here.


This filly has been superb over this strip. She also has a pair of runner-up finishes at the Fair Grounds in the Rachel Alexandra and the Fair Grounds Oaks respectively. I think she is a big price who isn’t out of her depth to make noise here. She is yet another who figures to vie for a hotly contested lead. I wanted to include her in any gimmicks but she would have to improve her speed figures immensely for me to consider her in a field of this caliber. I am going to eliminate her begrudgingly.

10-Champagne Anyone

In winning the Gulfstream Park Oaks, she put it all together that day with the addition of blinkers. This filly will try and work out a trip from around mid-pack but she is another who will have to improve on her speed numbers. I think the pace scenario gives her a puncher’s chance here so Champagne is someone who may find her way on the back end of any tris or supers.


This filly was last seen in a breakthrough victory in the Davona Dale at Gulfstream. That race was in March so she has had ample time to train up for this race. As I dig into her past performances, I see that she should find a good spot around the middle of the field. Although I root for small operations to do well in these kinds of races, I just think she is up against it so I am going to toss her out as well.

12-Street Bend

When you look to what prep race has been the most productive for this race in recent years, you head to New Orleans and the Fair Grounds Oaks which has produced numerous Kentucky Oaks winners. This filly showed significant improvement in taking the Fair Grounds Oaks but maybe she was compromised as the horse who will break to her immediate outside bled badly and did not finish. However, her trainer Larry Jones has won the Kentucky Oaks thrice and usually he is hard to dismiss. She has the right type of running style but I am not bullish on her chances here.

13-Serengeti Empress

Before the Fair Grounds Oaks, I was all in on this filly to win at Churchill. And then came that race in which she bled and did not finish. To the novices, it is time to abandon ship. As for me, I have watched closely how she has trained which has been nothing short of awesome. I wish this ‘Empress would have drawn better here but this is the hand her connections have been dealt. She is yet another who will be a part of a hot pace but of all the speeds drawn I think despite her wide draw she can hang on for something. Her trainer Tom Amoss has been exuding confidence in advance of the Kentucky Oaks; usually when trainers do that, I tend to pay close attention. This filly is one of the main players despite the draw so I feel she could provide tremendous value for those who still believe in her.

14-Restless Rider

She ran second in the Ashland at Keeneland in what was her 2019 debut. She looked like she hung down the stretch so she should move forward off that effort. The post shouldn’t bother this Restless one because she will break and drop over in an effort to make a belated run. The pace will be there for her so it is just a matter of whether she can work out a trip. If she has no hindrances, she has a real chance to win this race. I am inclined to use her on any gimmicks and multi-race wagers.

My Selections

1-Restless Rider: It took a lot of breaking down this race from a lot of angles but at the end of the day this filly is my choice to win the 2019 Kentucky Oaks. She may lead a gargantuan payoff for exacta, trifecta and superfectas.

2-Chocolate Kisses: Another huge price contender I think will revert to her closing style here. Her post is good for that tactic.

3-Serengeti Empress: Of all the speed horses signed up, I believe she could have the most staying power. Her wide draw will be tough but I expect a big effort. She has been training lights out as mentioned so the only reason I don’t have her on top is because there appears to be too much speed to allow her an easy trip. I still feel she stays on for a share.

4-Flor de la Mar: I really have been looking closely at this filly. At the end of the day, the talent is there but I think her lack of seasoning may cost her here. I do expect a good effort out of her.

There you have it. See how strong in my convictions I am when it comes to picking the Kentucky Oaks? I am taking a chance by leaving the favorite Bellafina off my selections but I have seen better than her fail. I will say this though. If I am right, the payoffs will be really sweet indeed.

So now it’s on to Kentucky Derby No. 145 on Saturday. As we head towards the Derby, I will give you one tidbit. The horse I will ultimately select will be a pick with strong conviction behind it. Who is it? You must wait until I piece together my preview later this week as I did for the Oaks. You will get my horse-by-horse analysis along with my selections.

Listen to Ken Trahan and Ed Daniels on the Three Tailgaters Show this Saturday morning on WGSO 990 AM New Orleans from 10 a.m. to noon through the web at or on the TuneIn app. At around 11:45, I will join them to discuss Kentucky Derby 145 in the hopes of hitting the exacta for my great and dear friend Ed Daniels. It’s a labor of love. I am well overdue for a winning Derby exacta. I have to win, I need to win. Anything less is just wrong. Once more I have great confidence in my pick for this Derby But full disclosure: If I do so, it’ll be my first Derby win since 1994. It’s well patt time to end that drought, don’t you think?

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George Pepis

George Pepis

Horse Racing Analyst

George Pepis provides racing analysis during each Fair Grounds racing season. He also shares commentary and selections for major stakes events and prep races around the country. In the past, George has hosted sports talk programming on WGSO 990am in New Orleans. He has served as both play-by-play and color analyst on Louisiana high school football radio and internet broadcasts.

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