On big race days, a big part of the appeal is that large, competitive fields provide a great opportunity to uncover live longshots, and the Longines Kentucky Oaks and Kentucky Derby Presented by Woodford Reserve on April 30 and May 1, respectively, at Churchill Downs are the definition of big race days.

We’ll have gambling posts later in the week looking for best bets, value plays, and longshots throughout the entirety of the two cards, so for this feature let’s focus in on the two big races: the Kentucky Oaks for 3-year-old fillies at 1 1/8 miles and the 1 ¼-mile Kentucky Derby for 3-year-olds.

Let’s start out with the Kentucky Oaks. While I do respect the favorites in this race – #5 Travel Column (3-1 morning-line odds), #10 Malathaat (5-2), and #12 Search Results (3-1) – I don’t think there is a whole lot separating them from the second tier, so in this race I’m going to swing big and play a couple of longshots on top and then try to add a couple of absolute bombs for third and fourth on trifecta and superfecta tickets.

I’ll try to beat the above three with a pair of runners in #1 Pauline’s Pearl and #5 Pass the Champagne:

Pauline’s Pearl (Eclipse Sportswire)

#1 Pauline’s Pearl (20-1): With 3-year-olds in the spring, I always like to see the upward trajectory of a racehorse improving at the right time of year, and this Tapit filly out of Grade 1 winner Hot Dixie Chick fits the bill. Looking at the Equibase, Beyer, and Brisnet speed figures, she has improved with each start this year for Hall of Fame trainer Steve Asmussen and comes into the race off a one-length win from off the pace in the Grade 3 Fantasy Stakes April 3 at Oaklawn Park. While there are no true need-the-lead types in this race, most of the runners seem to prefer to be in the top two or three, so I think it could set up well for Pauline’s Pearl to settle behind the top tier and have a slew of tiring targets in front of her entering the long Churchill Downs stretch. I’d be surprised if we get 20-1 odds to be honest, but I’ll be thrilled if we do.

#5 Pass the Champagne (15-1): Malathaat reeled in Pass the Champagne in the stretch of the Central Bank Ashland Stakes April 3 at Keeneland. Pass the Champagne seized command and opened up a two-length lead but could not hold on despite the short stretch for 1 1/16-mile races at Keeneland. So, what makes me think she can be more effective stretching out to 1 1/8 miles with the long stretch at Churchill Downs standing between her and an Oaks victory? It’s pretty simple: like Pauline’s Pearl above, I view this Flatter filly as a 3-year-old on the rise. She, too, has improved her Equibase, Beyer, and Brisnet speed figures in each of her three starts, and the Ashland was her first try around two turns after running in sprints in her first two races. Expect Pass the Champagne to improve with the 1 1/16-mile race under her belt, and I think she’ll be in the hunt at the top of the stretch with a real chance to win the Kentucky Oaks.

Bombs Away Underneath: Two fillies I think could vastly outrun their odds in this race to really spice up the exotic tickets are #9 Coach (50-1) and #11 Will’s Secret (30-1). Coach was a very nice 2-year-old who was disappointing in her first two starts as a 3-year-old when beaten by more than five lengths in both. She bounced back to run a nice third behind Pauline’s Pearl in the Fantasy Stakes, earning a career-best Equibase Speed Figure and Beyer Speed Figure and essentially pairing her best Brisnet speed rating for two-time Kentucky Oaks-winning trainer Brad Cox. Will’s Secret’s trainer, Dallas Stewart, won the Kentucky Oaks with Lemons Forever when she paid $96.20 for a $2 win bet in 2006, the biggest longshot in the history of the race. Stewart also ran 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. Will’s Secret was a well-beaten third for Stewart in the Grade 1 Central Bank Ashland Stakes April 3, but before that she won the Martha Washington Stakes and Grade 3 Honeybee Stakes, so she has a lot of talent for a 30-1 longshot.

Moving on to the Kentucky Derby, there is no doubt #14 Essential Quality (2-1) is a deserving favorite. The 2020 champion 2-year-old male is unbeaten in five starts, owns a win on the main track at Churchill, has a win on a sloppy track, and he’s among the fastest runners in the field on paper. I expect him to run well and I will use Essential Quality in my top three in exacta, trifecta, and superfecta bets while throwing out some of the other leading candidates. But … I do plan to try to beat him for the top spot in the Kentucky Derby because I think it’s a narrow gap between him and the other top 3-year-olds.

Originally, I planned to pick Curlin Florida Derby Presented by Hill 'n' Dale Farms at Xalapa winner Known Agenda to win, expecting him to be in the 8-1 to 10-1 odds range. But he was pegged at 6-1 on the morning line and drew the dreaded rail post, which has not produced a winner since Ferdinand in 1986. While I still might go with Known Agenda on top – I believe in the talent and the new starting gate unveiled in 2020 provides more room on the inside – I plan to reevaluate, so let’s instead focus on the longshots who could spice up the exotics.

In order of preference:

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#16 King Fury (SCRATCHED): The Grade 3 Stonestreet Lexington Stakes winner spiked a fever after his morning gallop on April 30 and was scratched from the race. ... I am one of those who believes one prep race is insufficient for the Kentucky Derby, but in King Fury’s case I am willing to make an exception because I really like the long-term future of this 3-year-old and I love his 20-1 morning-line odds. By two-time Horse of the Year Curlin out of Grade 1 winner Taris, King Fury returned from an extended layoff in the Grade 3 Stonestreet Lexington Stakes and ran a career-best race while winning by 2 ¾ lengths. He posted his best speed figures across the board with a 103 from Equibase, 95 from Beyer, and 95 from Brisnet. King Fury definitely gets a boost if the track comes up wet, he has a stakes win around two turns at Churchill Downs, and there is a chance he could improve in his second start of the year for trainer Kenny McPeek. I’m hoping the pace is honest to set up his closing kick.

#6 O Besos (20-1): My biggest concern here is that he becomes the wise-guy horse and gets bet down to 12-1 or something ridiculous like that, because this pick is all about value and at 20-1 or 25-1 you are getting a lot of bang for your betting dollar with O Besos. He ran significantly better that is looks on paper when third, beaten by two lengths, in the Twinspires.com Louisiana Derby. O Besos was really the only runner in that race to make up any ground in the stretch. In our Derby Data feature by Keeler Johnson, he noted that O Besos finished with a final eighth of a mile in :12.23 and a final three-eighths in :37.29. Given that the Louisiana Derby was at 1 3/16 miles, I think it’s reasonable to expect a similar late rally stretching out an extra sixteenth of a mile with six weeks rest. His speed figures are very competitive. There’s much to like with O Besos.

#19 Soup and Sandwich (30-1): Here is another runner who is better and faster than his odds indicate. As mentioned above, I liked Known Agenda quite a bit, so it’s no surprise that I also like the runner-up from the Florida Derby, who was plenty game in defeat. He has the tactical speed to gain good position from post position 19 (no, not ideal) and the length of the stretch to make his way over so he’s not hung incredibly wide on the first turn. I expect him to settle in just off the pace under a terrific rider in Tyler Gaffalione and get the jump on some of the late runners. With a 108 Equibase Speed Figure, a 90 Beyer Speed Figure, and a 98 Brisnet speed rating, he could hang around for a top-three finish for trainer Mark Casse at a monster price.