2021 Kentucky Oaks Cheat Sheet

Racing
Search Results, Travel Column, and Malathaat (left to right) are three leading contenders for the Kentucky Oaks April 30 at Churchill Downs. (Dom Napolitano-NYRA Photo/Hodges Photography-Amanda Hodges Weir/Keeneland-Coady Photography)

The $1.25 million Longines Kentucky Oaks regularly draws the best 3-year-old fillies in the country to Churchill Downs to compete against elite competition in the sister race to the Kentucky Derby Presented by Woodford Reserve.

Held annually on the Friday before the Kentucky Derby, the Kentucky Oaks is sometimes called “the run for the lilies” and “the Derby for fillies.” After the postponement in 2020 until September due to the COVID-19 pandemic, the Kentucky Oaks returns to its normal place on the schedule and will be held April 30, 2021, at the Louisville track.

Last year’s winner, Shedaresthedevil, established a new stakes record for the 1 1/8 miles by completing the Oaks in 1:48.28 while winning by 1 ½ lengths.

Like the Kentucky Derby, the Oaks has served as a springboard to dozens of stars and superstars over the years with standouts such as Ashado, Rags to Riches, Proud Spell, Rachel Alexandra, Blind Luck, Untapable, Abel Tasman, and Monomoy Girl prevailing just since the start of the 21st Century.

The 147th Kentucky Oaks will be televised on NBCSN as part of the Friday telecast scheduled to run from noon ET through 6 p.m. ET.

Read on for more information about all of the Kentucky Oaks contenders.


Coady Photography

1. Pauline’s Pearl (20-1 morning-line odds)

Jockey: Ricardo Santana Jr.

Trainer: Steve Asmussen

Owner: Stonestreet Stables

Career record: 5 starts – 2 wins – 2 seconds – 1 third

Career earnings: $461,500

Earnings per start: $92,300

Top Equibase Speed Figure: 98

Kentucky Oaks points: 120           

Pedigree: Tapit – Hot Dixie Chick, by Dixie Union

Color: Gray or roan

Running style: Stalker

Notable achievements and interesting facts: Often with major 3-year-old races the key to evaluating a race is to find the racehorse on an upward trajectory, and Pauline’s Pearl fits that profile. A Stonestreet Stables homebred by leading sire Tapit out of Grade 1 winner Hot Dixie Chick, Pauline’s Pearl was bred to be a star but she was well-beaten in her first two starts. She earned her first win on a sloppy track in February at Fair Grounds going 1 1/16 miles but that effort did little to convince bettors she was a viable option in her stakes debut when she ran second by three-quarters of a length at 18.90-1 odds in the Grade 3 Honeybee Stakes March 6 at Oaklawn Park. She was not overlooked in the Grade 3 Fantasy Stakes April 3 at the Arkansas track when she posted a clear win as the 4-5 favorite to punch her ticket to the Kentucky Oaks. Pauline’s Pearl earned a new career-top Equibase Speed Figure, Beyer Speed Figure, and Brisnet speed rating in the Fantasy and has improved her Equibase and Beyer numbers with each race. If she improves again, Pauline’s Pearl is a serious candidate to win April 30. Trainer Steve Asmussen won the Kentucky Oaks in 2005 with Summerly and in 2014 with Untapable.


Adam Coglianese/NYRA

2. Maracuja (20-1)

Jockey: Kendrick Carmouche

Trainer: Rob Atras

Owner: Beach Haven Thoroughbreds

Career record: 4 starts – 1 win – 2 seconds – 1 third

Career earnings: $119,600

Earnings per start: $29,900

Top Equibase Speed Figure: 99

Kentucky Oaks points: 40           

Pedigree: Honor Code – Patti's Regal Song, by Unbridled’s Song

Color: Gray or roan

Running style: Closer

Notable achievements and interesting facts: After making three starts in sprints at distances ranging from three-quarters of a mile to seven-eighths of a mile, Maracuja stretched out to 1 1/8 miles for her stakes debut in the Grade 3 Gazelle Stakes and significantly outran her 18.60-1 odds in a runner-up finish. Her 99 Equibase Speed Figure marked a 16-point increase from her previous best and offered hope that she might be far-better suited to longer races. By 2015 Whitney Stakes winner Honor Code out of Patti’s Regal Song, who was stakes-placed at 1 1/16 miles, it makes sense that she might excel with added distance. As mentioned in the comments about Gazelle winner Search Results, I do have some concerns about how slow the runners in that race finished as well as the quality of competition, but Maracuja took a major step forward in that race and has never finished outside the top three. Still, she very likely will need to improve again in her second start around two turns and fourth race of the year to be a serious player in the Kentucky Oaks.


Eclipse Sportswire

3. Clairiere (5-1)

Jockey: Tyler Gaffalione

Trainer: Steve Asmussen

Owner: Stonestreet Stables

Career record: 4 starts – 2 wins – 2 seconds – 0 thirds

Career earnings: $350,492

Earnings per start: $87,623

Top Equibase Speed Figure: 100

Kentucky Oaks points: 94      

Pedigree: Curlin – Cavorting, by Bernardini

Color: Bay

Running style: Stalker/closer

Notable achievements and interesting facts: If you are planning to back Travel Column, you also should strongly consider Clairiere for your exacta and trifecta bets since these two have finished first and second in their last three races. Clairiere finished second by a length to Travel Column in their first meeting last fall in the Grade 2 Golden Rod Stakes at Churchill Downs. She beat her familiar rival by a neck in February in the Grade 2 Rachel Alexandra Stakes Presented by Fasig-Tipton at Fair Grounds before finishing second to her at the New Orleans track in the Grade 2 Twinspires.com Fair Grounds Oaks March 20. While she was well-beaten in the Fair Grounds Oaks, Clairiere has trained well since then for trainer Steve Asmussen, she will be well-rested, and she owns a win and a second in two races on the main track at Churchill. Like several others here, Clairiere appears well-equipped to handle 1 1/8 miles as a filly by two-time Horse of the Year Curlin out of multiple Grade 1 winner Cavorting, winner of the 2016 Personal Ensign Stakes at 1 1/8 miles. There is a chance she might be a bit overlooked facing a strong group, but Clairiere never runs a bad race and could find herself in the winner’s circle should she take a step forward and get a favorable pace and trip setup. Asmussen won the Kentucky Oaks in 2005 with Summerly and in 2014 with Untapable.


Eclipse Sportswire

4. Crazy Beautiful (15-1)

Jockey: Jose Ortiz

Trainer: Ken McPeek

Owner: Phoenix Thoroughbred III

Career record: 7 starts – 3 wins – 3 seconds – 0 thirds

Career earnings: $388,365

Earnings per start: $55,481

Top Equibase Speed Figure: 96

Kentucky Oaks points: 128           

Pedigree: Liam’s Map – Indian Burn, by Indian Charlie

Color: Gray or roanRunning style: CloserNotable achievements and interesting facts: As her name would indicate, Crazy Beautiful is an eye-catching gray filly. She enters the Kentucky Oaks off of a mini-breakout performance when securing her first graded stakes victory with a sustained rally to win the Grade 2 Gulfstream Park Oaks when closing from last to first March 27. Crazy Beautiful is a responsive filly with a nice turn of foot, and she was a stakes winner and multiple graded-stakes placed entering the Gulfstream Park Oaks, so she had proven class entering the race. She measures up well with most of the field on paper with competitive speed figures, although she is a bit less consistent than the probable favorites for the Kentucky Oaks having lost three times by six or more lengths. In her lone start on this main track, Crazy Beautiful finished second in the Grade 3 Pocahontas Stakes last September. There is not an abundance of speed in the field, but there probably is at least enough to ensure an honest pace and set up her closing kick. Jockey Jose Ortiz won the Kentucky Oaks in 2019 on Serengeti Empress. Ken McPeek-trained Swiss Skydiver finished second in the Kentucky Oaks last year and won the Preakness Stakes in her next start, defeating Kentucky Derby winner and eventual Horse of the Year Authentic.


Coady Photography

5. Pass the Champagne (15-1)

Jockey: Javier Castellano

Trainer: George Weaver

Owners: R. A. Hill Stable, Black Type Thoroughbreds, Rock Ridge Racing, BlackRidge Stables, and James Brown

Career record: 3 starts – 1 win – 2 seconds – 0 thirds

Career earnings: $115,170

Earnings per start: $38,390

Top Equibase Speed Figure: 98

Kentucky Oaks points: 40           

Pedigree: Flatter – Champagne Taste, by Distorted Humor

Color: Chestnut

Running style: Stalker

Notable achievements and interesting facts: Pass the Champagne was two lengths clear in early stretch in the Grade 1 Central Bank Ashland Stakes April 3 at Keeneland and looked like a winner, but she could not hold off hard-charging Malathaat and finished second by a head. Coming out of a sparkling maiden win but making only the third start of her career, Pass the Champagne delivered a big effort in the Ashland and earned a career-best 98 Equibase Speed Figure and 93 Brisnet speed rating. The Ashland also was Pass the Champagne’s first try around two turns after running in a pair of seven-furlong sprints earlier in the year, so she should have a better stamina foundation on Kentucky Oaks day. Of the probable longshots for the Kentucky Oaks, I think she has the best chance to win the race. I’d be surprised if she does not run well April 30 at Churchill Downs. Jockey Javier Castellano won the Kentucky Oaks in 2016 aboard Cathryn Sophia.


Eclipse Sportswire

6. Travel Column (3-1)

Jockey: Florent Geroux

Trainer: Brad Cox

Owner: OXO Equine

Career record: 5 starts – 3 wins – 1 second – 1 third

Career earnings: $509,184

Earnings per start: $101,837

Top Equibase Speed Figure: 99

Kentucky Oaks points: 132        

Pedigree: Frosted – Swingit, by Victory Gallop

Color: Gray or roan

Running style: Stalker/press the pace

Notable achievements and interesting facts: Travel Column is a consistent and classy filly who figures to draw plenty of support in the Kentucky Oaks coming off a 2 ¾-length victory in the Grade 2 Twinspires.com Fair Grounds Oaks March 20. Making her third start of the year with six weeks of rest, there is a very good chance this filly by Frosted turns in a career-best race for 2020 Eclipse Award-winning trainer Brad Cox, who also trains unbeaten champion Essential Quality, the probable favorite for the Kentucky Derby Presented by Woodford Reserve May 1. Since winning her debut in September 2020 on this main track at Churchill Downs, Travel Column has raced exclusively in Grade 1 or Grade 2 stakes with two wins, a runner-up finish by a neck, and one third. In addition to her debut, Travel Column also won the Grade 2 Golden Rod Stakes at 1 1/16 miles at Churchill, so she likes this main track. Her speed figures are very competitive with this group and there is little reason to expect Travel Column won’t run a big one for Cox, who teamed with Travel Column’s jockey, Florent Geroux, to win the Kentucky Oaks in 2018 with Monomoy Girl and in 2020 with Shedaresthedevil.


Coady Photography

7. Ava’s Grace (SCRATCHED)

Jockey: David Cohen

Trainer: Robertino Diodoro

Owner: Cypress Creek Equine

Career record: 4 starts – 1 win – 1 second – 2 thirds

Career earnings: $156,400

Earnings per start: $39,100

Top Equibase Speed Figure: 96

Kentucky Oaks points: 40           

Pedigree: Laoban – Cover Girl Elle, by Out of Place

Color: Bay

Running style: Pacesetter/press the pace

Notable achievements and interesting facts: In her first try stretching out in distance in 1 1/16-mile Fantasy Stakes April 3 at Oaklawn Park, Ava’s Grace set the pace and held on gamely late to finish second by a length to winner Pauline’s Pearl. Her 96 Equibase Speed Figure was a 12-point jump from her previous top in three sprint races, suggesting that perhaps her high cruising speed is even more potent when trying longer distances. In her second start navigating two turns and third race of the year, Ava’s Grace is a prime candidate to improve in the Kentucky Oaks and her running style should place her in the mix approaching the stretch. Based upon pedigree, the 1 1/8-mile distance is a bit of a concern but her tactical speed becomes a major asset in this race with not a ton of early speed entered. Ava’s Grace fits the bill as an intriguing Oaks contender to fill out the trifecta or superfecta at a big price.


Moraz (inside) (BENOIT photo)

8. Moraz (30-1)

Jockey: Flavien Prat

Trainer: Michael McCarthy

Owner: Don Alberto Stable

Career record: 5 starts – 1 win – 1 second – 3 thirds

Career earnings: $133,640

Earnings per start: $26,728

Top Equibase Speed Figure: 94

Kentucky Oaks points: 42           

Pedigree: Empire Maker – Malvina, by A.P. Indy

Color: Dark bay or brown

Running style: Stalker/press the pace

Notable achievements and interesting facts: A well-beaten third in her only race as a 2-year-old, Moraz made a splash in her 2021 debut with an 11-length runaway victory Jan. 8 at Santa Anita Park. She followed with a third-place finish in the Grade 3 Las Virgenes Stakes before running second by a head to Beautiful Gift in the Grade 3 Santa Ysabel Stakes in March. The second betting choice in a four-horse field for the Santa Anita Oaks, Moraz finished 5 ¾ lengths behind winner Soothsay in a somewhat disappointing third-place finish that earned a 77 Equibase Speed Figure that was 17 points off her career top. Not only would Moraz need to rebound from a subpar effort in the Santa Anita Oaks, she probably would need to improve her speed figures by five to 10 points to be a win threat and that’s a tall order against a very good field. 


Coady Photography

9. Coach (50-1)

Jockey: Luis Saez

Trainer: Brad Cox

Owner: Kueber Racing

Career record: 7 starts – 3 wins – 1 second – 2 thirds

Career earnings: $224,740

Earnings per start: $32,106

Top Equibase Speed Figure: 95

Kentucky Oaks points: 26          

Pedigree: Commissioner – And Stay Out, by Exchange Rate

Color: Dark bay or brown

Running style: Stalker

Notable achievements and interesting facts: Coach showed plenty of promise as a 2-year-old but she has not been nearly as effective in 2021. The Commissioner filly won the first three starts of her career by a combined margin of 16 ½ lengths, including a facile win in the Rags to Riches Stakes at Churchill Downs. She closed her 2-year-old campaign with a third-place finish to Travel Column in the Grade 2 Golden Rod Stakes at the Louisville track. Beaten by 5 ¼ lengths and 7 ¼ lengths in her first two races as a 3-year-old in stakes at Oaklawn Park, Coach did turn in an improved effort when third in the Grade 3 Fantasy Stakes on April 3, finishing 1 ¾ lengths behind winner Pauline’s Pearl. Coach earned a career-top 95 Equibase Speed Figure in the Fantasy and is trending in the right direction for trainer Brad Cox, who won the Kentucky Oaks in 2018 with Monomoy Girl and last year with Shedaresthedevil. Stablemate Travel Column looks like the more likely winner from the Cox barn, but he should have Coach primed for a big race, too, and the price should be enticing if you’re looking to fill out your trifecta or superfecta tickets.


Coady Photography

10. Malathaat (5-2)

Jockey: John Velazquez

Trainer: Todd Pletcher

Owner: Shadwell Stable

Career record: 4 starts – 4 wins – 0 seconds – 0 thirds

Career earnings: $412,150

Earnings per start: $103,038

Top Equibase Speed Figure: 98

Kentucky Oaks points: 110          

Pedigree: Curlin – Dreaming of Julia, by A.P. Indy

Color: Bay

Running style: Stalker

Notable achievements and interesting facts: While Malathaat did not amass as many qualifying points for the Kentucky Oaks as several of her opponents, expect her to vie for favoritism with a perfect 4-for-4 record. The filly by two-time Horse of the Year Curlin out of Grade 1 winner Dreaming of Julia, by 1992 Horse of the Year A.P. Indy, boasts a stamina-laden pedigree and enters the Kentucky Oaks out of a rallying victory by a head in the Grade 1 Central Bank Ashland Stakes April 3 at Keeneland. A $1,050,000 purchase at the 2019 Keeneland September yearling sale, Malathaat won all three of her starts as a 2-year-old and then returned from a four-month layoff to win the Ashland, giving her a solid chance to improve in her second start of the year. Malathaat looks like the one to beat for owner Shadwell Stable, whose founder Sheikh Hamdan bin Rashid Al Maktoum died March 24 at age 75. Trainer Todd Pletcher is seeking his fourth Kentucky Oaks win, having won with Ashado (2004), Rags to Riches (2007), and Princess of Sylmar (2013). Jockey John Velazquez earned his lone Kentucky Oaks win aboard the aforementioned Ashado.


Coady Photography

11. Will’s Secret (30-1)

Jockey: Jon Court

Trainer: Dallas Stewart

Owner: Willis Horton Racing

Career record: 7 starts – 3 wins – 0 seconds – 3 thirds

Career earnings: $383,300

Earnings per start: $54,757

Top Equibase Speed Figure: 94

Kentucky Oaks points: 80           

Pedigree: Will Take Charge – Girls Secret, by Giant's Causeway

Color: Dark bay or brown

Running style: Stalker

Notable achievements and interesting facts: Trainer Dallas Stewart authored the biggest upset in Kentucky Oaks history when Lemons Forever won the race in 2006 and paid $96.20 for a $2 win bet. Don’t expect Will’s Secret to be close to the 47.10-1 odds Lemons Forever was sent off at in 2006, but the Will Take Charge filly should be a solid price for a trainer whose horses often run huge race at big prices in important races (see below). Will’s Secret needed four races to earn her first victory Dec. 20, 2020, at Fair Grounds. She then opened her 3-year-old season by winning the Martha Washington Stakes by 5 ¼ lengths from off the pace and the Grade 3 Honeybee Stakes by three-quarters of a length while leading from start to finish, both at Oaklawn Park. Will’s Secret flattened out late in her final Kentucky Oaks prep when third in the Grade 1 Central Bank Ashland Stakes April 3 at Keeneland and her speed figures and record at Churchill Downs (two thirds in two starts) are a bit underwhelming. She’s probably a better candidate to spice up the exacta payout than win the Kentucky Oaks, and that’s something at which the aforementioned Stewart is somewhat of a specialist. He’s finished second in the Kentucky Derby twice with Golden Soul at 34.50-1 odds in 2013 and Commanding Curve at 37.80-1 in 2014 and second twice in the Preakness with Macho Again at 39.90-1 odds in 2008 and Tale of Verve at 28.50-1 in 2015.


Eclipse Sportswire

12. Search Results (3-1)

Jockey: Irad Ortiz Jr.

Trainer: Chad Brown

Owner: Klaravich Stables

Career record: 3 starts – 3 wins – 0 seconds – 0 thirds

Career earnings: $299,000

Earnings per start: $99,667

Top Equibase Speed Figure: 103

Kentucky Oaks points: 150           

Pedigree: Flatter – Co Cola, by Candy Ride

Color: Dark bay or brown

Running style: Press the pace

Notable achievements and interesting facts: Unbeaten in three starts with strong speed figures, Search Results most likely will be one of the top betting choices for the Kentucky Oaks. With wins in the one-mile Busher Stakes and Grade 3 Gazelle Stakes, both at Aqueduct, there is some question about the quality of opposition she has defeated in New York after pressing an easy pace in both races. She beat only five fillies in the Busher and finished her final three-eighths of a mile in :39.08 in the 1 1/8-mile Gazelle despite rating just behind an opening half-mile in :50.09. That said, this is a talented filly on the rise with a win at this distance and, on paper, Search Party is absolutely fast enough to win the Kentucky Oaks. She’s in terrific hands with four-time Eclipse Award winner Chad Brown and looms a top win candidate. Brown, jockey Irad Ortiz Jr., and owner Klaravich Stables all are seeking their first win in the Kentucky Oaks.


Eclipse Sportswire

13. Competitive Speed (50-1)

Jockey: Chris Landeros

Trainer: Javier Gonzalez

Owner: John C. Minchello

Career record: 7 starts – 3 wins – 0 seconds – 2 thirds

Career earnings: $116,595

Earnings per start: $16,656

Top Equibase Speed Figure: 87

Kentucky Oaks points: 30           

Pedigree: Competitive Edge – Shopped Out, by Mineshaft

Color: Chestnut

Running style: Stalker/closer

Notable achievements and interesting facts: Well-beaten in three starts since winning the 6 ½-furlong Glitter Woman Stakes Jan. 2 at Gulfstream Park, it’s fair to question whether Competitive Speed might ultimately find her niche sprinting. She most recently ran third by four lengths in the 1 1/16-mile Gulfstream Park Oaks after she was beaten by eight lengths while third in the one-mile Davona Dale Stakes, both Grade 2 races at Gulfstream Park. With a career-best 87 Equibase Speed Figure, it is difficult to envision a scenario where Competitive Speed winds up getting her picture taken in the Kentucky Oaks winner’s circle. Perhaps the best-case scenario might be a speed duel up front that sets the Oaks up for deep closers and Competitive Speed rallies late for a minor share. A top candidate to be the highest odds on the toteboard.


Coady Photography

14. Millefeuille (20-1)

Jockey: Joel Rosario

Trainer: Bill Mott

Owner: Juddmonte Farms

Career record: 5 starts – 1 win – 3 seconds – 0 thirds

Career earnings: $127,800

Earnings per start: $25,560

Top Equibase Speed Figure: 91

Kentucky Oaks points: 44          

Pedigree: Curlin – Bandana, by War Front

Color: Bay

Running style: Stalker

Notable achievements and interesting facts: A Juddmonte homebred, Millefeuille is a filly by two-time Horse of the Year Curlin from a nice Juddmonte family anchored by third dam (maternal great-grandmother) Toussaud, who produced 2003 Belmont Stakes winner Empire Maker and Grade 1 winner Honest Lady (Millefeuille’s grandam [maternal grandmother]). Millefeuille showed promise as a 2-year-old with a win and two seconds in three starts, including a runner-up finish to Malathaat in the Grade 2 Demoiselle Stakes. She disappointed in her 2021 debut, thanks in part to a troubled trip, when seventh in the Grade 2 Davona Dale Stakes Feb. 27 at Gulfstream Park. Four weeks later, she looked like a winner entering the stretch of the Grade 2 Gulfstream Park Oaks with an eye-catching move to take command, but Millefeuille could not sustain her rally and ran second by 2 ¼ lengths to Crazy Beautiful. She would need to improve her speed figures significantly to win the Kentucky Oaks April 30, but if you excuse her troubled season debut, she has been consistent and professional in her other four races and could run a big race in her third start of the year. Juddmonte, whose founder Khalid Abdullah died Jan. 15 at 85, won the Kentucky Oaks in 2001 with Flute.

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