2018 Kentucky Oaks Expert Picks with Betting Odds and Predictions

by Trevor Whenham - 5/1/2018

The Kentucky Derby is the main event this weekend at Churchill Downs, but the Kentucky Oaks at the heart of Friday's card is a heck of a race in its own right. If you are actually in Louisville then Oaks day is actually the more enjoyable day than the Derby in some ways - more manageable crowds, slighter fewer big hats, but just as much bourbon and a pile of good races.

The Oaks is, to oversimplify dramatically, the Derby equivalent for three-year-old fillies. Horses have gained points all spring to get here, and it is a very prestigious race for these young horses to win. It's not quite the same, though - only 14 horses enter instead of 20 for the Derby, and this is not the start of a crazy three-race test like it is for the colts.

This year's race, which has had some late injuries and travel woes that have mixed up the field, is a very top-heavy race. Here's a look at how the class of the 14-horse field shapes up (Horse, Jockey, Trainer, Track Odds):

Monomoy Girl, Florent Geroux, Brad Cox, 2/1: In six career starts she has won five times in convincing fashion and was beaten once by just a neck. That loss came at Churchill, but she also won twice here, so she is comfortable on the track. She's very good, and Geroux is a strong rider. She's an automatic play in the exotics, but what doesn't make her my top pick is that I don't love her breeding - at least in terms of getting this distance.

Midnight Bisou, Mike Smith, William Spawr, 5/2: Mike Smith has a heck of a double potential this weekend - this filly followed by favored Justify in the Derby . He's won the race twice, including last year. The filly has three graded stakes wins this year, including a very nice win in the Santa Anita Oaks last time out. I'm a big believer in her, and she's my top pick.

My Miss Lilly, Joe Bravo, Mark Hennig, 10/1: The third choice is 10/1 - it's not a deep race. This filly has run only four times, so experience is a concern. Her last race was her longest, and also her best, though, so she's growing into herself. I don't think she is good enough to win yet, but she could be a piece of it.

Coach Rocks, Luis Saez, Dale Romans, 12/1: She's from the first crop of Preakness winner Oxbow, she has won two straight very nicely, and her jockey is red hot. There are things to like here. But she is jumping up in class, and her win two back was in a maiden race - her eighth. She has figured things out lately, but she still has a long way to go. Intriguing, but not a pick.

Chocolate Martini, Javier Castellano, Tom Amoss, 12/1: This is one of those crazy stories that shouldn't happen. In February she was claimed out of a turf race for $25,000. She was run back just a couple weeks later in an allowance race on dirt and won. And then she went to the Grade 2 Fair Grounds Oaks and won that, too. So, her connections bought her for $25,000 and won $240,000 seven weeks later. Crazy. It must truly suck to be the former owners. It's a great story, but I don't think she's good enough for it to continue.

Rayya, Drayden van Dyke, Bob Baffert, 12/1: This is an odd story. This is her first start in the U.S. after a career in Dubai. She convincingly won the UAE Oaks at the beginning of March. That earned her an ambitious spot in the UAE Derby - a key Kentucky Derby prep. She was second in that race, though she was 18 lengths behind winner Mendelssohn . That was on March 31. Since then she hasn't raced, but she has moved to California and to the barn of Baffert specifically to target this race. This is a lot to ask, but she's a nice, tough filly, and Baffert has won this race three times. I'll have some cash on this one.

Sassy Siena, Gary Stevens, Brad Cox, 15/1: She is coming in off a win, and she has run well on the rail twice before, so there are some things to like here. I'm a sucker for Stevens in a big race, too. But that last race was glacially slow down the stretch, and she only barely won it. She's taking a step up in class here. I certainly wouldn't take any less than this price.

Classy Act, Brian Hernandez Jr., Bret Calhoun, 15/1: I'm just not a believer. Last time out she was alone on the lead for a very long time, she controlled a reasonable pace, and she still faded late to finish fourth. Now she's running further against a stronger field, and there is very little chance that she will get the lead alone this time around. Nothing to like here.

Take Charge Paula, Jose Ortiz, Kiaran McLaughlin, 15/1: This filly is going to be a part of the early pace scenario. And she's been first or second in eight of nine starts, so she is consistent. But she has run longer than a mile only twice in her career, and they haven't been her best races. I just don't think she can get the distance.

Eskimo Kisses, Corey Lanerie, Ken McPeek, 15/1: The biggest thing that stands out here is that her maternal grandmother is Derby-winning filly Winning Colors, which is a pretty great omen for this weekend. On a more practical basis, she has been second in her last two outings - the only stakes races of her career. And both horses that beat her are here. Lanerie knows Churchill Downs well and could get a good piece of things here at this price. An exotics play.

Wonder Gadot, John Velazquez, Mark Casse, 20/1: This is a horse that seems to have peaked too soon. She won two graded at two and looked like she would be a major contender in this race. But this year she has been second twice and third twice and hasn't looked nearly as sharp. It hasn't been ideal, but there is talent here, and the connections are strong. At this price she'll be a part of the exotics.

Want free Kentucky Derby picks for 2018? Our experts are the best Kentucky Derby handicappers in the nation, and you can get their picks free (first-time clients only), Get $60 worth of Kentucky Derby premium members' picks free .

Raphael Esparza is the former Race and Sportsbook Director at the Aria Hotel in Las Vegas, where his horse racing connections are second to none. He’s been picking winners at the track for more than 20 years, and Kentucky Derby Saturday he will dominate Churchill downs. Esparza will be handicapping not only Saturday Kentucky Derby but also he will start the weekend with Friday Churchill Downs winners (Kentucky Oaks). Esparza is coming off big horse winners at the Arkansas Derby, Lexington Stakes, and the Florida Derby. Esparza is one of the best horse racing handicappers in the nation, and not only will he have action all day on Kentucky Derby Saturday but Esparza is releasing a 8-Unit Kentucky Derby Head-to-Head matchup. Esparza is already up over $900 the past month, and don't forget last year on Derby day Esparza racked up over $1,100 in profits and went a perfect 3-0 $1,420 in Kentucky Derby Head-to-Head matchups. Jump back on the saddle again with the former Vegas Sports Book director and walk with him to the winning circle.

Start:	December 15, 2024 @ 12:00 PM
Expert:	Tony George
Free $60 Account Sign Up