Kaitlin Free’s Kentucky Oaks Rundown

May 2, 2019

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Kaitlin Free

Past The Wire’s Kaitlin Free has done an annual preview of the Kentucky Oaks contenders for several years running. This year’s edition will feature each filly with their chances to run well and reasons they may come up short. Contenders will be featured from the rail moving out.


Irad Ortiz Jr. Up, Trained by Dallas Stewart

Why She Fits :

Although she has only raced five times and only made her stakes debut a month ago, Out For a Spin’s form is sneaky good. Her record stands at three wins in five starts with one third. She raced for the first time in mid November and broke her maiden a month later at Fair Grounds where she remained before transferring to Keeneland in April. Out For a Spin’s lone stakes victory came in her only stakes start, a G1 at that. Although she only won by a neck, she defeated one of the toughest fields in all of the Oaks preps, taking down fellow entrants Jaywalk, Restless Rider, and Chocolate Kisses gamely. In that performance she scored an 88 Beyer and recorded a Thoro-Graph 3. Out For a Spin’s Thoro-Graph numbers have progressed from a 13 to a 9 to a 3 in 2019. This is a serious filly that is only getting better with every start.

Out For a Spin drew the rail for the Kentucky Oaks, but this actually could be a decent spot for her. She doesn’t need the lead or to be all that close, and in a race packed with speed she will absolutely benefit taking back after the break. Will also get a ground saving rail trip. If she stalks and tracks another filly the way she did in the Ashland she sets herself up to be one of the big hopes to take down our top contender. Out For a Spin also gets the services of reigning Champion Jockey Irad Ortiz Jr. This filly is also proven on an off track.

Why She Loses :

If Out For a Spin is to lose the Kentucky Oaks it could come from the bounce theory. Running a Thoro-Graph number of 9 and dropping a 3 next out is quite a significant jump. Though she is getting better with every start as stated above, that win could have taken a bit out of her. She’ll need to improve by several lengths to come level with Bellafina. These cautions could be enough for some to steer clear of her completely.


Julien Leparoux Up, Trained by Mark Casse

Why She Fits :

Most people spend time every year looking for that “buzz” horse in both the Kentucky Derby and Oaks. Should there be a buzz horse for the fillies this year, this is probably your girl. Like By My Standards she has been raising some eyebrows in the mornings at Churchill Downs. She spends as much time as she can every morning on the track and makes the most of every step she takes on the surface. Throwing out her performance last out in the Ashland at Keeneland, Chocolate Kisses has been the picture of consistency. That day at Keeneland her jockey Tyler Gaffalione was instructed to keep Chocolate Kisses a little closer to the pace, stepping outside of her usual stalking preference. Combined with perhaps might have been a bounce potential, that was a recipe for a flat showing. Now armed with Julien Leparoux in the Oaks, he fits her come from behind style and will give her that opportunity. She will have plenty of speed to stalk and could get a ground saving trip while lurking. She may not be good enough to win as her numbers have shown, but she is definitely one to include in your supers and trifectas. A very Wonder Gadot-esque filly.

Why She Loses :

If you’re simply looking for fillies that are win contenders, Chocolate Kisses may not be your cup of tea. Yes she is consistent and is a very confident mover, but her best numbers are a notch below our top contenders. Should she get caught a little more forward leaving post 2 than she would like, she could use up a good amount of energy. This one could be a toss up for handicappers and bettors. She fits into the exotics, but probably isn’t the best choice to win.


Ricardo Santana Jr. Up, Trained by Steve Asmussen

Why She Fits :

If you are looking for a filly peaking at the right time look no further. Lady Apple is coming into the Kentucky Oaks with her best self and is the most experienced in the field. She started early on in her 2YO year and has became a different horse at age three. Lady Apple has found versatility and appreciates the extra distance. She likes to stalk or press the pace and will benefit from all of the early speed predicted. Fillies drawn inside with ground saving and off of the pace trips historically do well in the Oaks and hit the board frequently. She really fits here in the big picture. After having taken a lengthy break to grow up from August to February, she has been unbeaten since. Lady Apple’s numbers have gotten better with each start and will continue to follow that pattern. Her Fantasy win over fellow entrant Motion Emotion was very game and earned her a Thoro-Graph number of 5. This filly could be poised to run as good as a 2 or 1 next out which puts her right in contention for the win. Her maiden and allowance score this year had her a bit closer up to the front runners but still pressing. Theoretically she could fill in anywhere in the middle throughout the race without compromising her chances. That type of versatility wins big races. Long time partner Ricardo Santana Jr.’s style fits her like a glove. Lady Apple is proven over an off track and anything close to her morning line will be a gift.

Why She Loses :

While most consider this filly to be peaking, others are skeptical that she may be running well over a track she really likes. All three of her starts in 2019 have came at Oaklawn Park. Can she handle such a task in foreign territory? The quality of fillies she has defeated has been suspect. Though she will be coming into the race in career best form, a new environment and tougher competition could prove to be a tall order.


Flavien Prat Up, Trained by Simon Callaghan

Why She Fits :

Bellafina comes into the Kentucky Oaks as confident as any filly in recent memory. She has been absolutely perfect so far in 2019 and has trained without a hiccup. She ran extremely fast numbers as a 2YO before a disappointing performance in the Breeders’ Cup Juvenile Fillies at Churchill Downs. With all of that behind her, Bellafina has ran two Thoro-Graph 1’s this season – far better than any other filly in this race. She could run the same race she has lately without improving and still win this race. Should Bellafina continue to step forward, the rest of the field will be racing for second. She has defeated fellow entrants Serengeti Empress and Flor de la Mar in previous starts. Her post should allow her to settle in a decent stalking or just off of the pace position without issue. The Kentucky Oaks is projected to have a decent amount of speed, giving Bellafina the pace she needs to run at. Even in the event of an off track she should handle it just fine. Her Las Virgenes victory was on a track rated good and she won’t mind a bit of moisture. She and usual jockey Flavien Prat make an excellent team and it will take a career best performance for someone to beat them on Friday.


Why She Loses :

Despite seeming perhaps heads and shoulders above some of these fillies, Bellafina still enters this race with question marks. One of the most popular questions being asked is the type of fields she has beaten in California. Bellafina has consistently defeated five horse fields and a lot of the same fillies her whole career. Doug O’Neill’s Enaya Alraab was beginning to sneak up on her and probably would with extra distance, but Enaya Alraab has been sidelined with injury. So who has she actually defeated out west? Her wins are impressive without a doubt, but the quality of her competitors has been suspect. With her only poor performance coming outside of California and Churchill Downs at that, the change of scenery could also be a question.



Joel Rosario Up, Trained by Bob Baffert

Why She Fits :

Anyone who is involved in racing knows the most basic rule when it comes to Classic races : do not dismiss Bob Baffert. Although she may be a longer shot in this field, ignore Flor de la Mar at your own risk. She created a buzz over the winter as one of Baffert’s most impressive horses in the morning often cranking out big works. Flor de la Mar lived up to the hype in her debut and won in hand. Following that win she was entered in an allowance race in a field she should have thrashed. She encountered a little trouble and came up with a flat effort. After that race many hopped off of the train and dismissed her chances of being anything special. Baffert was extremely puzzled by her effort and couldn’t explain the off performance other than the track condition. He has always liked Flor de la Mar a great deal and still says she could hang with anyone at her best. In the Santa Anita Oaks she gave a glimmer of hope running a very credible second to Bellafina, seeming to find her form again. This filly has hidden assets and the pedigree to go the distance. With a stamp of approval from Joel Rosario and Bob Baffert, she would be worth a stab at those odds.


Why She Loses :

The caution mark when it comes to Flor de la Mar is very simple, she lacks experience. Many of the fillies in this year’s Oaks have raced double or even triple what she has. Flor de la Mar has only raced a total of three times and has yet to leave Southern California. Throwing an inexperienced horse into a race such as this almost never results in a win. Bringing up the aforementioned allowance loss from March, the only thing to blame her bad showing on was the sloppy track. Should an off track come up on Oaks day, that combined with her lack of racing miles could be her undoing.



Manny Franco Up, Trained by Rodolphe Brisset

Why She Fits :

Even though she comes into the Kentucky Oaks as a longshot, you must respect the tenacity of Positive Spirit. This filly tries hard every time she runs. Trainer Rodolphe Brisset is one of the most brilliant young minds in racing and he has always thought a lot of this girl. She has a history of finding a little trouble, but still runs her hardest and almost always shows up. If you throw out the terrible race she had in the Rachel Alexandra at Fair Grounds, Positive Spirit has done next to nothing wrong. She ran a big ThoroGraph 3 as a 2YO in her Demoiselle victory and many considered her to be the leading Oaks contender for the East Coast. She was given over a month off after her trip to Fair Grounds and rebounded with a second in the Gazelle Stakes at Aqueduct. Now that Positive Spirit is back on her game, she could be a nice price horse to use in your exotics. She is a half sister to Kentucky Derby winner Always Dreaming by a Triple Crown sire. Her royal breeding alone makes her interesting.


Why She Loses :

Even though we admire many Positive Spirit’s attributes, those alone won’t get the job done against the likes of Bellafina and others. Her best does not match up to the top contenders and she would need to put in a Herculean effort to score against this group. Just like in the Derby, the New York prep quality is often significantly lesser than areas like California or Florida. On paper and theoretically this is a tall order to come out on top.



Javier Castellano Up, Trained by John Servis

Why She Fits :

Jaywalk comes into this race as one of the most puzzling horses currently in training. She had an incredible juvenile campaign capped off by a jaw dropping performance in the Breeders’ Cup Juvenile Fillies. Since that win, Jaywalk seems to have lost form and has came up empty in both of her 2019 performances. Despite this a few still believe she has some upside. That Championship sealing win came at none other than Churchill Downs and it is safe to say she really likes this track. There is a great deal of speed in this race including herself. If she happens to grab the early lead, the others could opt to let her go on with it and may accidentally write her off. Should Jaywalk get the lead, Javier Castellano will take advantage of it. If her numbers at two are any example she could be on another slow ascent to a top performance. Jaywalk loves Churchill Downs and would relish on a sloppy track. If Castellano can use her to control the pace like she has done in the past, there is a chance for them to sneak away.


Why She Loses :

For Jaywalk to win this year’s Kentucky Oaks it has to be the perfect storm. She must find her best stride again and shake away early. With several other speedy fillies entered, the likelihood of her being alone on the lead is very slim. She has proven she just isn’t tactical enough to sit another kind of trip. Other than the fact that she is a Champion many wonder why she was entered off of her most recent efforts. Jaywalk’s connections still believe she can bounce back so that’s why she is here. She also must buck some serious history to get the win. You will have to go all the way back to 1999 to the great Silverbulletday to find the most recent filly to capture both the Juvenile Fillies and the Kentucky Oaks. Silverbulletday was also a significantly better filly than Jaywalk.



Mike Smith Up, Trained by Thomas Van Berg

Why She Fits :

Motion Emotion is another filly that comes into the Kentucky Oaks that has consistency on her side. She gives you her best effort every time she runs. She seems to have blossomed from age two to three, never finishing worse than second in four starts so far in 2019. With her front running style, she is drawn a bit wider than connections probably would have hoped. Motion Emotion is probably tactical enough to sit just off of the leader in this field but would have to step a bit outside of her comfort zone. If you are a believer in horse heart, this filly has a big one and could appeal to you. Definitely could be a logical choice for the exotics. Will get a huge boost with new rider Mike Smith who is quite good with fillies like Motion Emotion.


Why She Loses :

Two major concerns jump out right away about Motion Emotion in this particular race. If you look at her form she has one start over the Churchill Downs surface on a sloppy track. Although she was still a juvenile and had a rough trip, this filly probably won’t love another off track running. Especially if she doesn’t get clear sailing to the front she will take a lot of mud to the face should the track come up off as expected. Another major red flag is that fight she could encounter to get the upper hand early. One of the other speed fillies, Jaywalk, is right beside her in gate 7. Should these two hook up immediately and battle it will be suicidal for both of them. How Motion Emotion comes out of the gate will really predict what type of race she will have. At this point in time that is anyone’s guess.



Channing Hill Up, Trained by Wayne Catalano

Why She Fits :

Liora is a filly that seems to be peaking at the right time. Although she hasn’t won in 2019, she earned her spot in this race with two runner up performances in the Fair Grounds preps. She is one of the more experienced fillies in the field and shouldn’t turn a hair under these conditions. After a brief month off before making her 3YO debut, numbers would suggest that Liora is on the upswing in her career. Running second to both Serengeti Empress and Street Band this year, she matched their winning Thor-Graph numbers in those races. To be beaten and match the winner’s number is difficult and must have an exceptionally impressive race in defeat. If Liora can avoid trouble here and in her future races the numbers will match up with our top tier fillies. Liora also loves Churchill Downs and has two wins here, including a G2 victory over a sloppy track. That form checkmark alone makes her even more interesting. Channing Hill and Wayne Catalano really like this filly and have been with her every step of her career. Will also appreciate the extra distance.


Why She Loses :

Unfortunately for Liora and her backers she is somewhat of a puzzling sort. While she may be consistent, she consistently finds trouble. Most of the chart comments for every race in her career state that she was very wide or bumped. In a large field with many talented competitors there certainly is no margin for error. Should Liora get a clean trip and a sloppy track like she did in her impressive Golden Rod win, her very best may still be a hair short of a couple others. Probably more of a superfecta / tri play rather than a win.



Chris Landeros Up, Trained by Ian Wilkes

Why She Fits :

Champagne Anyone is another talented filly that has long been searching for her niche. Her big score came last out in the Gulfstream Park Oaks over a game Dunbar Road and Cookie Dough. It was visually one of the more impressive Oaks prep victories. Champagne Anyone showed lots of promise early on in her career and has never been worse than fourth ever. She likes to cash checks and tries hard every time. One thing this filly has on her side is versatility. If she is taken outside of her comfort zone she will still put in a top class effort. Things could go wrong for Champagne Anyone and she would still be classy enough to overcome obstacles. A sloppy track shouldn’t bother her and she will be just fine at the Oaks distance. Horses like Champagne Anyone are always around at the finish and she will be extremely usable on your tickets. If she puts in another effort like last out, she could be in contention for the top prize.


Why She Loses :

Even though Champagne Anyone is tactical enough to overcome most obstacles, no one likes to see a troubled trip in a Classic race. Like Liora stated above, she’s another filly that often ends up wide or bumped in the midst of a run. Trouble in a 14 horse field is enough to cost even the best in the race the win. That being stated, she is in our top tier of fillies entered but isn’t quite the top contender.



Luis Saez Up, Trained by Alexis Delgado

Why She Fits :

Jeltrin comes into the Kentucky Oaks as what some would consider a “fluke” victory. She earned 50 points and a berth into the race with her 51-1 upset in the Davona Dale Stakes. In that particular race she defeated both Jaywalk and Champagne Anyone. Connections have said that the light bulb really came on that day and she has trained fantastic ever since. Though she only has that win and a maiden claiming victory to her credit, Jeltrin has some big things to like in the Oaks. Her running style sets up well for this field and won’t be used up early. She is the type of filly that can encounter a wide trip or traffic and should still have enough left in the tank. This distance really hits her between the eyes. Jeltrin is unproven on an off track but is the best bred filly in the race to handle moisture in the track. She is coming into the Kentucky Oaks very fresh and has had a bit of a break since the Davona Dale. One would suspect a bounce after that effort, but she has had over two months away. Jeltrin retains long time partner Luis Saez – an under the radar top jockey these days. Keep Jeltrin in mind at a price.


Why She Loses :

Although her number in the Davona Dale was spectacular, Jeltrin will need to step up even further to be a contender. She was awarded a Thoro-Graph number of 5 for that effort, a good number but will need to jump substantially. Another concern is her lack of travel miles. Jeltrin has never left Florida and has had every start at Gulfstream aside from her claiming win at Gulfstream Park West. A change of scenery and a step up in class could be a major concern for this filly.



Sophie Doyle Up, Trained by Larry Jones

Why She Fits :

If you are looking for the Oaks filly that the mainstream media will latch onto, it is probably this one. The duo of Street Band and Sophie Doyle is sure to get major press. Lots of comparisons will probably be made to Rosie Napravnik and her previous Oaks winners. Though she may not be as good as Untapable or Believe You Can, a win from Street Band is not out of the realm of possibility. She is one of the more experienced fillies in the race and is very well traveled. She is certainly at the top of her game and has blossomed at three. Her numbers indicate she will only get better. If Street Band steps up again on Friday, she could be close to our top contenders. Distance and an off track shouldn’t be a problem. Connections have the utmost confidence in Sophie and so do we.


Why She Loses :

Street Band is one of the fillies in this race that you just doesn’t really know where to put. She’ll need to step up to challenge the likes of Bellafina and a couple others. She needs to avoid any traffic trouble that comes with a wider draw. Unfortunately without many strikes for or against her, Street Band could be forgotten in this group.



Jose Ortiz Up, Trained by Tom Amoss

Why She Fits :

The Serengeti Empress of old very much fits into this race. In her final Kentucky Oaks prep she bled and was vanned off, leaving many questions unanswered. After having several months off following a tiring juvenile season, Serengeti Empress returned emphatically in the Rachel Alexandra at Fair Grounds. She looked like she could be the Oaks favorite following that performance. Track work indicates that Serengeti Empress is back to her old self and the risk of bleeding is behind her. A pattern can be spotted in her past performances, she usually has a big effort followed by trouble. If that rings true she will be back on her game on Friday. If she runs her Rachel Alexandra race or better she is a real threat. Another feather in her cap is her previous monster performance over the Churchill Downs track. Her Pocahontas victory exuded early class and was one of the most impressive wins there last season. She unfortunately came up empty at the Breeders’ Cup, but you can scratch that race out due to her strenuous campaign and previous effort. She is back on form and should be ignored at your own peril. The services of Jose Ortiz can only help her chances and he will guide her to the right trip.


Why She Loses :

Serengeti Empress pulling up at Fair Grounds is the last image everyone has of her and won’t forget it here. Her poor efforts have had valid excuses, but some may be afraid to trust her again. Often when a horse bleeds in a prior start it does take a bit out of them. She is the awkward piece of the puzzle in this race. Her post isn’t ideal and with her anything can happen. Rain may also throw another obstacle in her way.



Brian Hernandez Jr. Up, Trained by Kenny McPeek

Why She Fits :

Restless Rider rounds out the Kentucky Oaks field as your final speed type horse. She has been the picture of consistency her entire career, never finishing worse than second. Her ThoroGraph and Beyer numbers land her as one of the top contenders in the race. Nothing has indicated that she will regress or be a bounce candidate. Restless Rider is the kind of filly you want to bring to a Classic race. She always gives her best and isn’t afraid to be in a fight. Often horses feel defeated if they are passed in the stretch and sometimes lose their fire. Not this girl. If it isn’t her day, she’ll give you the same A+ effort tomorrow like nothing happened. That type of tenacity cashes checks win or lose. Jockey Brian Hernandez Jr. knows this filly inside and out and knows how to work out the best trip for her. Should she adjust to her gate draw, she could be scary.


Why She Loses :

It is obvious that Restless Rider was the loser of the post draw. For a filly that likes to be so close to the pace, gate 14 is a less than ideal spot. Hernandez will have to really hustle her out and get after her right away to shift over. In a race where distance limitations could come into play, wasting precious energy so early will compromise her chances. Restless Rider needs to save all the ground to have the best shot. That will a difficult task from such a wide draw.

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