2021 Kentucky Oaks tipsheet

Profile Picture: J. Keeler Johnson

April 30th, 2021

The Kentucky Derby (G1) might receive more press, but the Friday’s $1.25 million Kentucky Oaks (G1) at Churchill Downs looks just as competitive. The 1 1/8-mile race for three-year-old fillies has drawn a full field of 14, with a bevy of logical contenders capable of reaching the winner’s circle.

Kentucky Oaks pick

  • #10 Malathaat

Other horses of interest

  • #6 Travel Column
  • #3 Clairiere
  • #4 Crazy Beautiful
  • #12 Search Results

Kentucky Oaks wagers

  • $20 to win on #10 Malathaat
  • $2 trifecta: 10 with 6 with 1,3,4,11,12 ($10)
  • $2 trifecta: 10 with 1,3,4,11,12 with 6 ($10)

Kentucky Oaks contenders

#1 Pauline’s Pearl carved out a solid winter campaign at Oaklawn Park, where she won the Fantasy S. (G3) and finishing second in the Honeybee S. (G3), even though she was compromised by a slow pace in the latter. A beautifully bred daughter of Tapit, out of Hot Dixie Chick, Pauline’s Pearl might still have upside for two-time Oaks-winning trainer Steve Asmussen, but the waters get deeper at Churchill Downs.

#2 Maracuja showed some late interest to rally and finish second in the Gazelle S. (G3), but she couldn’t keep pace with undefeated winner Search Results through the final furlong. The competition is tougher in the Kentucky Oaks, and it’s hard to gauge how Maracuja will perform in her first start away from the slow, tiring track at Aqueduct.

#3 Clairiere has squared off against key Kentucky Oaks rival Travel Column on three occasions and picked up a narrow victory in the Rachel Alexandra (G2). But race dynamics favored Clairiere in the Rachel Alexandra (I would argue she caught Travel Column napping on a lonely lead), and Clairiere finished 2 3/4 lengths behind her rival in the Fair Grounds Oaks (G2). Clairiere is a logical contender to crack the Kentucky Oaks trifecta, but turning the tables on Travel Column will be tricky.

#4 Crazy Beautiful unleashed a powerful last-to-first rally to win the Gulfstream Park Oaks (G2) by daylight, even though the early pace was modest and seemingly favorable to speed horses. Crazy Beautiful showed good form at Churchill last season, when she finished second with a troubled trip in the Pocahontas (G3), and she is eligible to step forward in her third start of the season.

#5 Pass the Champagne ran too good to lose in the Ashland (G1), when she finished second by a head against Kentucky Oaks favorite Malathaat. But the daughter of Flatter benefited from tracking a slow pace and led by daylight in midstretch, so she couldn’t have asked for a better setup. More challenging circumstances may await at Churchill Downs.

#6 Travel Column arguably lost focus when she struck the lead prematurely in the Rachel Alexandra, where she came up a neck short against Clairiere. But Travel Column sandwiched that defeat between confident victories over Clairiere in the Golden Rod S. (G2) and Fair Grounds Oaks, with the latter triumph by 2 3/4 lengths. With two preps under her belt, Travel Column should be fit for a career-best effort, which gives trainer Brad Cox a chance to win his third Kentucky Oaks in four years.

#7 Ava’s Grace didn’t run badly in her two-turn debut, when she carved out the pace in the Fantasy and finished second, behind Pauline’s Pearl. But her career-best 91 Brisnet Speed rating looks a bit light, and she’ll need improvement to challenge against tougher competition at Churchill Downs.

#8 Moraz hit the board in three straight Road to the Kentucky Oaks qualifiers at Santa Anita, but took a step backward when she faltered to finish third in the Santa Anita Oaks (G2). The daughter of Empire Maker was beaten 5 3/4 lengths, after she set a slow pace, and she’ll need a rebound to factor at Churchill Downs.

#9 Coach won her first three starts convincingly, including the Rags to Riches S. at Churchill Downs. But she is winless from four attempts on the Road to the Kentucky Oaks, and most recently finished third in the Fantasy. Coach is a capable filly, but her form lines suggest she ranks a cut below the top Kentucky Oaks contenders.

#10 Malathaat has shown signs of stardom and is undefeated in four starts. I loved her victory in the Demoiselle (G2) last fall, when she struggled over a sloppy track but still gained a ton of ground to win comfortably. She was just as impressive in the Ashland to kick off 2021, when she sprinted the final five-sixteenths in :29.54 to overcome a slow pace and win by a head. As a daughter of Curlin, Malathaat is bred to improve with maturity for trainer Todd Pletcher, who has won the Kentucky Oaks three times. With a perfect draw, Malathaat will be very tough to beat.

#11 Will’s Secret was helped by a slow pace when she won the Honeybee but hindered by another pedestrian tempo when she rallied to finish third in the Ashland. Will’s Secret has kept good company, with wins over Pauline’s Pearl and Coach, and might not be out of the hunt to hit the board at a big price.

#12 Search Results is undefeated in three starts, and most notably romped to an easy, pace-tracking victory in the Gazelle. But her best form has come over the slow, tiring track at Aqueduct, and Search Results has yet to face the stiffest competition. The transition to the faster track at Churchill Downs, and the step up in class, will be a test of her talent.

#13 Competitive Speed has been something of a “pick up the pieces” type at Gulfstream Park, where she rallied from off the pace to finish third in the Davona Dale (G2) and Gulfstream Park Oaks. But she has been defeated twice by Crazy Beautiful and has lost ground from the eighth pole to the wire in her last three starts, which suggests 1 1/8 miles may stretch the limits of her stamina.

#14 Millefeuille looked destined for victory in both the Demoiselle and Gulfstream Park Oaks, but faltered on both occasions to finish second, behind late-charging rivals. The daughter of Curlin is versatile in terms of running style and enters off a series of bullet workouts, but she risks a wide trip from post 14 and will need improvement to turn the tables on Malathaat and Crazy Beautiful.