Magic Man’s breakdown of the 2021 Kentucky Oaks

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Churchill Downs entrance Barbaro statue

As a horse racing enthusiast, this week is more special than any other. Consider not even a full year ago this prestigious race was run in September due to the pandemic. It felt totally discombobulated as a traditionalist not seeing the Run for the Roses at the start of May.

Just the mere fact that the Oaks and Derby are to be run in their rightful dates makes me ecstatic and I am very fired up to see how these two races will play out.

An early synopsis of the Kentucky Oaks has me believing it to be a very wide open rendition. Malathaat is the tepid 5-2 morning line favorite and comes in off a courageous win in the Ashland at Keeneland in her last outing. A pair of Fair Grounds-based horses merit big consideration as well, considering as of late our historic facility has been a gold mine to the Kentucky Oaks.

Now let us dive into this race in greater detail with analysis and my selections for this renewal of the Kentucky Oaks.

Race 11 Longines Kentucky Oaks (Grade I) POST Time – 5:51 PM
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PPs & Selections
PP (Race 11)
Exacta / Trifecta / Superfecta / Pick 3 (Races 11-12-13) /Double (Oaks-Derby) Pick 3 (Oaks-Old Forester Turf Classic-Derby) / Super Hi-5
Churchill Downs STAKES

Purse $1,250,000. For Fillies, Three Years Old. One And One Eighth Miles.

P# PP Horse  Virtual
A/S Med Jockey Wgt Trainer M/L Live Odds
1 1 Pauline’s Pearl (KY) [ ] 3/F R Santana, Jr. 121 S M Asmussen 20/1
2 2 Maracuja (KY) [ ] 3/F K Carmouche 121 R Atras 20/1
3 3 Clairiere (KY) [ ] 3/F T Gaffalione 121 S M Asmussen 5/1
4 4 Crazy Beautiful (KY) [ ] 3/F J L Ortiz 121 K G McPeek 15/1
5 5 Pass the Champagne (KY) [ ] 3/F J Castellano 121 G Weaver 15/1
6 6 Travel Column (KY) [ ] 3/F F Geroux 121 B H Cox 3/1
7 7 Ava’s Grace (KY) [ ] 3/F D Cohen 121 R Diodoro 50/1
8 8 Moraz (KY) [ ] 3/F F Prat 121 M W McCarthy 30/1
9 9 Coach (KY) [ ] 3/F L Saez 121 B H Cox 50/1
10 10 Malathaat (KY) [ ] 3/F J R Velazquez 121 T A Pletcher 5/2
11 11 Will’s Secret (KY) [ ] 3/F J K Court 121 D Stewart 30/1
12 12 Search Results (KY) [ ] 3/F I Ortiz, Jr. 121 C C Brown 3/1
13 13 Competitive Speed (KY) [ ] 3/F C Landeros 121 J E Gonzalez 50/1
14 14 Millefeuille (KY) [ ] 3/F J Rosario 121 W I Mott 20/1

Owners: 1 – Stonestreet Stables, LLC (Barbara Banke) ; 2 – Beach Haven Thoroughbreds, LLC (Ara Aprahamian) ; 3 – Stonestreet Stables, LLC (Barbara Banke) ; 4 – Phoenix Thoroughbred III, Ltd. (Aamer Abdulaziz Ahmed) ; 5 – R. A. Hill Stable (Raymond A. Hill, III), Black Type Thoroughbreds (Jake Ballis), Rock Ridge Racing, LLC (Codee S. Guffey), BlackRidge Stables, LLC (William Daugherty) and James Brown ; 6 – OXO Equine, LLC (Lawrence Best) ; 7 – Cypress Creek Equine (Kevin Moody) ; 8 – Don Alberto Stable (Carlos Heller) ; 9 – Kueber Racing, LLC (Rick Kueber) ; 10 – Shadwell Stable (Rick Nichols) ; 11 – Willis Horton Racing, LLC (Willis D. Horton) ; 12 – Klaravich Stables, Inc. (Seth Klarman) ; 13 – John C. Minchello ; 14 – Juddmonte (Fahad bin Khalid)
Breeders: 1 – Stonestreet Thoroughbred Holdings LLC; 2 – River Bend Farm Inc., Austin Musselman& Janie Musselman; 3 – Stonestreet Thoroughbred Holdings LLC; 4 – Carolyn R. Vogel; 5 – Preston Madden; 6 – Mr. & Mrs. Bayne Welker Jr. &Denali Stud; 7 – Southern Equine Stables, LLC; 8 – Don Alberto Corporation; 9 – Three Lyons Racing, LLC; 10 – Stonestreet Thoroughbred Holdings LLC; 11 – Willis Horton Racing LLC; 12 – Machmer Hall; 13 – White Fox Farm; 14 – Juddmonte Farms Inc
Pedigrees (Sire – Dam, by Dam Sire): 1 – Tapit – Hot Dixie Chick , by Dixie Union ; 2 – Honor Code – Patti’s Regal Song , by Unbridled’s Song ; 3 – Curlin – Cavorting , by Bernardini ; 4 – Liam’s Map – Indian Burn , by Indian Charlie ; 5 – Flatter – Champagne Taste , by Distorted Humor ; 6 – Frosted – Swingit , by Victory Gallop ; 7 – Laoban – Cover Girl Elle , by Out of Place ; 8 – Empire Maker – Malvinia , by A.P. Indy ; 9 – Commissioner – And Stay Out , by Exchange Rate ; 10 – Curlin – Dreaming of Julia , by A.P. Indy ; 11 – Will Take Charge – Girls Secret , by Giant’s Causeway ; 12 – Flatter – Co Cola , by Candy Ride (ARG) ; 13 – Competitive Edge – Shopped Out , by Mineshaft ; 14 – Curlin – Bandana , by War Front;
Sire of Maracuja standing at Lanes End
Sire of Crazy Beautiful standing at Lanes End


Pauline’s Pearl
Comes in off a resolute win in the Fantasy at Oaklawn in her last out and she is a consistent sort. I just don’t feel she appears fast nor good enough to win this. Let’s move on.

Ran a strong second to Search Results in the Gazelle in her most recent effort. Comes off that lone stakes try and appears up against it with these fillies so she is another I will toss aside.

The winner of the Rachel Alexandra two starts back over Travel Column saw the latter reverse the decision in the rematch by taking the Fair Grounds Oaks. Clairiere gets a rider switch to Tyler Gaffalione; don’t you think Tyler has to atone for his foolish ride aboard Swiss Skydiver in last fall’s running of the Oaks? This filly has a really good chance here. I like the switch in riders and believe Gaffalione will put her into the race early to set it up for her to finish big. A definite player in my book.

Crazy Beautiful
I watched this filly’s win in the Gulfstream Park Oaks in her last out and came away visually impressed at her getaway that day. It’s rare you get an Ortiz at a price as you have that here. The only nagging concern is she does not appear to pair up good races. If she does reproduce that last out, I think she has a shot. She also is making the third and most important start off the layoff. One to consider in the back end of your exotics and if things fall right not the worst stab for a win wager.

Pass the Champagne
I look at her form and marvel at how gutsy she was in finishing second in the Ashland in her first try against stakes horses. What is the oddsmaker trying to say making her 15-1 while the horse who nipped her is the 5-2 favorite? I am tempted to use her in multi race gimmicks yet that’s a predominant theme for me in this year’s Kentucky Oaks. That is a testament to how deep this field is. Tough call for me though.

Travel Column
Trainer Brad Cox is looking for his third Oaks win over the last four years and this filly gives him a really good chance to do so. She is 2-for-2 over the Churchill strip and has the right type of style to win here. She impressed in taking the Fair Grounds Oaks in her last outing and it stands to reason that she is a major factor for me. A definite must use for me here.

Ava’s Grace
Has a license to improve in her third start off the layoff but I feel this is asking too much of her. An easy one to toss out in this loaded field.

A well beaten third in her last out in the Santa Anita Oaks, Moraz gets a positive rider switch to Flavien Prat. I don’t think she is going to be around at the end and despite her consistency I don’t envision a scenario where she has any shot.

The last of Brad Cox’s three starters probably will be the forgotten one considering who else he has. I am not the least bit interested as she has been handled by a few in this field previously. There is no way she reverses that trend.

Has not lost in four starts and comes off a courageous win in the Ashland. In a race that is complex, I get why she is the early favorite but by no means is she unbeatable. I wouldn’t completely toss her out but for those that do, I also wouldn’t fault you either.

Will’s Secret
When you look at a race of this magnitude, one thing is always tried and true. You see trainer Dallas Stewart in the entry box. He has been known to spring upsets in these high caliber races. This gal was well-backed and finished a well-beaten third in the Ashland in her last start. I feel she is a couple of rungs below the top flight competition here.

Search Results
Unblemished through three starts, she answered the class question in taking the Gazelle at Aqueduct in her last out. Drawing the 12 hole does not help matters. Obviously she makes sense in any multi-leg wagers but can you be brazen enough to throw her out? I really am in a quandary when it comes to that because I see a precocious and talented filly.

Competitive Speed
I have no idea what business this filly has in here. There is nothing in her form that suggests she even remotely competes. Her name in this spot is the antithesis of the situation so I will confidently pass on her.

Draws the far outside and comes in off a distant second in the Gulfstream Park Oaks. Gets reunited with rider Joel Rosario so that could help but I feel there is too much to overcome. I just don’t feel she has a real shot.

My Selections

  1. Clairiere–Sometimes in racing you have to go with your gut, and this filly has been top of the list for me all winter and into the spring. Slightly more upside comes to bear as she takes this year’s Kentucky Oaks in what promises to be a thriller.
  2. Travel Column–Brad Cox has the Kentucky Oaks track record you cannot ignore, and this filly could very well get him his fourth win in the last five. It would not surprise me if she won here just feel my top choice is slightly better.
  3. Crazy Beautiful–My price play here is one who I don’t think she can beat the top two but if they stumble I am not afraid to say she can do real damage. At the worst, she is on trifecta and superfecta tickets.
  4. Malathaat–What made this for me is recent history. Until the Gulfstream preps convince me they can roll out top class horses, I will side with New Orleans and my top two picks. It is not to discredit this gal as she looks plenty good but pay attention to the morning line. It is telling that she is 5-2 and the second place finisher in her last is 15-1. That is called a clue.

That is all for my look at the Kentucky Oaks and it promises to be a superlative weekend with the Derby being in its rightful place on the calendar. I will have that highly-anticipated closer look at the 2021 Kentucky Derby with horse by horse analysis and selections soon so stay tuned for that on Friday night. As always, may your winners be plentiful and your wallets be fat.

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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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