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Todd Pletcher can tie the record for most Kentucky Oaks wins by a trainer when he sends out Gambling Girl in the 2023 Kentucky Oaks on Friday at Churchill Downs. The 55-year-old Pletcher has won the Lilies for the Fillies four times, one shy of the record jointly held by Hall of Fame trainers Woody Stephens and D. Wayne Lukas. In the Kentucky Oaks 2023, Pletcher will saddle Gambling Girl, a 15-1 longshot in the 2023 Kentucky Oaks odds. The Brad Cox-trained Wet Paint is the 5-2 favorite in the 14-horse 2023 Kentucky Oaks field, while Botanical, who also is trained by Cox, is 4-1.

The 2023 Kentucky Oaks post time is 5:51 p.m. ET on Friday. With the Kentucky Oaks' large and wide-open field making for some tough decisions, you'll want to see what racing reporter and analyst Michelle Yu has to say before making any 2023 Kentucky Oaks picks, considering she nailed this race last year.

Few people in racing are as well-connected as Yu. An on-air host and reporter who has provided racing analysis for TVG, HRTV and the Breeders' Cup, Yu has spent a lifetime in racing. Prior to her television career, she worked for trainers Steve Asmussen and Ron Moquett. She also is married to Santa Anita-based trainer Ryan Hanson.

Yu also has tremendous handicapping chops. In a wide-open Derby in 2021, she gave out Medina Spirit, who crossed the finish line first, as the winner at 12-1. In Pool 5 of the Derby Future Wager last year, she suggested a play on All Other 3-Year-Olds, which cashed at a whopping 18-1 when Rich Strike won. In last year's Kentucky Oaks, she correctly called the winner, Secret Oath, and also hit the exacta.

Since the end of February, she has crushed the Saudi Cup, riding a 15-1 winner, nailed Derma Sotogake to win the UAE Derby and hit the exacta in the Santa Anita Derby. Her return on investment over that time is $5.08 for every $1.

Now, Yu has handicapped the 2023 Kentucky Oaks odds, made her picks and constructed her bets. You can only see them at SportsLine.

Top 2023 Kentucky Oaks expert picks

One surprise: Yu is high on the chances of Affirmative Lady, even though she is a 10-1 longshot. A Grade 2 winner who captured the Gulfstream Park Oaks in her last start, Affirmative Lady is trained by Graham Motion. He has had only one previous starter in the Oaks, Summer Soiree, who finished 10th in 2011.

Yu likes that Motion had the confidence to enter Affirmative Lady in a Grade 2 stakes as a maiden last year. "This daughter of Arrogate has a few foundation races to fall back on and still needs to move up, but she's usable," Yu told SportsLine. Yu is using Affirmative Lady prominently in her 2023 Kentucky Oaks bets. See who else to back at SportsLine.

How to make 2023 Kentucky Oaks picks, bets

Yu's top pick is a horse who "should love the added ground" on Friday. She also is high on a double-digit longshot who is "bred to be a champ." She's sharing which horses to back only at SportsLine.

So what horse wins the Kentucky Oaks 2023? And what double-digit longshot is a must-back? Visit SportsLine to see Yu's picks for the Kentucky Oaks, all from the expert who nailed this race last year, and find out.

2023 Kentucky Oaks odds, picks, post positions 

HorseOddsPost No. Projection
Wet Paint5-27SEE PICKS
Botanical4-16SEE PICKS
Southlawn8-14SEE PICKS
Affirmative Lady10-113SEE PICKS
Pretty Mischievous10-114SEE PICKS
Defining Purpose12-111SEE PICKS
Wonder Wheel12-15SEE PICKS
And Tell Me Nolies15-19SEE PICKS
Flying Conection15-110SEE PICKS
Gambling Girl15-13SEE PICKS
The Alys Look15-12SEE PICKS
Dorth Vader20-112SEE PICKS
Mimi Kakushi20-11SEE PICKS
Promiseher America30-18SEE PICKS