Brad Cox has trained two of the last three Kentucky Oaks winners, and he'll try to make it three of four when the 2021 Kentucky Oaks goes to post at 5:51 p.m. ET on Friday at Churchill Downs. Cox trained 2020 winner Shedaresthedevil and 2018 winner Monomoy Girl. He has two horses in the 2021 Kentucky Oaks field, 50-1 long shot Coach and Search Results, who is one of the favorites in the 2021 Kentucky Oaks odds at 3-1.

Those Kentucky Oaks 2021 contenders will be among the fillies trying to chase down 5-2 favorite Malathaat, an undefeated horse trained by Todd Pletcher. With 13 of the nation's fastest fillies competing for $1.25 million in prize money, the action should be intense. Before making any 2021 Kentucky Oaks picks, be sure to see the top 2021 Kentucky Oaks bets and predictions from SportsLine's Jody Demling.

A fixture in the horse racing world who has been writing about, talking about and betting on races for years, Demling enters the 2021 Kentucky Oaks after a major heater in 2020: At one point last year, he picked the winners of six straight races: the Saudi Cup, Gotham Stakes, Rebel Stakes, Louisiana Derby, Florida Derby and Belmont Stakes.

This is the same handicapper who hit the Derby-Oaks double at Churchill Downs nine times in the last 12 years. That means he held a ticket with the winners of both the Kentucky Oaks and Derby all but three times in his last 12 tries.

He opened last season's Triple Crown schedule on a heater too. At last year's Belmont, Demling said Tiz the Law was clearly the class of the field, and Barclay Tagg's horse pulled away for a convincing 3 3/4-length victory. Anyone who has followed him is up huge.

Now, with the 2021 Kentucky Oaks field locked, Demling is sharing his picks and predictions at SportsLine. Go here to see them.

Top 2021 Kentucky Oaks predictions

One shocker: Demling is fading Malathaat, even though she is undefeated and the top favorite at 5-2 in the latest Kentucky Oaks odds 2021. In fact, Demling says Malathaat barely even hits the board. Pletcher has made it clear he believes Malathaat is a superstar, but there are reasons for concern in this race.

Demling likes her upside, but she faces multiple horses who have already performed well at Churchill Downs. She's only appeared in one race as a three-year old and won by a head at the Ashland Stakes on April 3. There are better values available in a talented 2021 Kentucky Oaks field, making Malathaat a horse to fade in your 2021 Kentucky Oaks bets.

Another curveball: Demling is high on Clairiere, even though she's an underdog in the Kentucky Oaks 2021. The daughter of 2007 Preakness Stakes winner Curlin, Clairiere is trained by Steve Asmussen, who also trained Curlin. Asmussen has won three Triple Crown races in his career and is also a two-time Kentucky Oaks winner.

Clairiere has finished in the top two in each of her four races, with two wins and two runner-up finishes. That includes a win at Churchill Downs to kick off her season in October, when she improved upon her time at the same distance one month later on this track. Even though she's more of a stalker/closer, don't discount her speed since her top Equibase Speed Figure is 100, making her just one of two fillies to reach triple-digits. Clairiere has the pedigree, trainer and running style to include in your 2021 Kentucky Oaks bets, according to Demling.

How to make 2021 Kentucky Oaks picks, bets

Demling is especially high on a huge double-digit underdog who "will be flying in the end." Demling is sharing which horse it is, along with his entire projected leaderboard, over at SportsLine.

Which horse wins the Kentucky Oaks 2021? And what huge underdog does Demling say contends? Check out the latest 2021 Kentucky Oaks odds below, then visit SportsLine to see Demling's picks for the Kentucky Oaks.

2021 Kentucky Oaks odds

Search Results3-1
Travel Column3-1
Crazy Beautiful15-1
Pass the Champagne15-1
Pauline's Pearl20-1
Will's Secret30-1
Ava's Grace SCR
Coach 50-1
Competitive Speed50-1