Live Longshots and Value Bets for Kentucky Oaks, Kentucky Derby Day

Regally bred Charge It is a prime longshot play in the Kentucky Derby for ABR handicapper Mike Curry. (Eclipse Sportswire)

Big race days are a fantastic opportunity for bettors because full fields of talented horses mean plenty of value to be found, and there is no bigger race day on the horse racing calendar than Kentucky Derby day.

This year’s Longines Kentucky Oaks May 6 at Churchill Downs and the Kentucky Derby Presented by Woodford Reserve May 7 drew appealing race cards across what figures to be two incredible days of betting. There are six stakes races on Oaks day and eight stakes on Kentucky Derby day with hundreds of thousands of people expected to pour into Louisville for the marquee event.

NBC Sports will provide comprehensive coverage up to the Kentucky Derby and will show the race live at approximately 6:57 p.m. ET Saturday. The network’s on-site broadcast begins Friday, May 6, with a five-hour show from 1 p.m to 6 p.m. ET on USA Network that will present live racing from Churchill culminating in the Oaks for 3-year-old fillies, scheduled to go off at 5:51 p.m. ET. On Saturday, May 7, coverage from Churchill begins at noon ET on USA Network and then switches to NBC from 2:30 to 7:30. That telecast will feature live racing from the Derby undercard as well as previews, analysis, and features.

So without further ado, let’s take a look at a few live longshots and value bets I have identified to try to cash some big tickets this weekend!

Friday, May 6

Race 7, Alysheba Stakes Presented by Sentient Jet, 2:09 p.m. ET

#6 Fulsome (8-1): He’s not a huge longshot by any means, but I do think the 8-1 morning-line odds offer a ton of value for what looks a little like the typical post-hype sleeper. After making the switch from turf to dirt last year, the Into Mischief colt ripped off four wins in five starts before an unplaced finish at long odds in the Grade 1 Pennsylvania Derby. He overcame adversity in his return from a six-month layoff in the Grade 3 Oaklawn Park Mile by rallying powerfully to win by a neck, and that race should set him up well here. He won at this track and distance last year in the Grade 3 Matt Winn Stakes in one of the best races of his career.

Race 8, Edgewood S. presented by Forcht Bank, 3:03 p.m. ET

#9 New Year's Eve (12-1): She has run well in all three career starts and enters off a third-place finish in the Allen Black Cat LaCombe Memorial Stakes, in which she was beaten by only a length in her stakes debut. Trainer Brendan Walsh wins at an elite percentage when adding blinkers and I think she has a solid chance to win at a big price if she can stay just a little bit closer to the pace early in this race.

Race 9, Eight Belles Stakes presented by TwinSpires, 4:04 p.m. ET

#9 Awake At Midnyte (15-1): After running third in the Grade 2 Rachel Alexandra Stakes Presented by Fasig-Tipton and fourth in the Grade 1 Central Bank Ashland Stakes, Awake at Midnyte cuts back from two-turn races to seven-eighths of a mile. She ran a terrific race when second by less than a length at this distance Jan. 8 at Santa Anita Park in the Grade 2 Santa Ynez Stakes and should fit nicely with this group while shortening up for the Eight Belles.

Race 11, Longines Kentucky Oaks, 5:51 p.m. ET

#13 Shahama (15-1): With so much top-end talent in the race like Nest, unbeaten Kathleen O. and Echo Zulu, and Arkansas Derby third-place finisher Secret Oath, there are bound to be some talented fillies that slip through the cracks. One I expect to significantly outrun her 15-1 morning-line odds is Shahama. No, I don’t like the post position, but this Munnings filly has, by all accounts, trained impeccably for the Oaks leading up to the race. She posted her fourth clear win in as many starts Feb. 18 in the UAE Oaks Presented By Jafza at Meydan Racecourse in Dubai, when she overcame a terrible start and a wide trip to post an eye-catching two-length score. You can’t ask for much more from a 15-1 longshot who happens to be a half-sister (same dam [mother], different sire [father]) to 2010 Preakness winner Lookin At Lucky. I’ll try to connect on exactas/trifectas keying Shahama and Kathleen O.

Saturday, May 7

Race 5, Longines Churchill Distaff Turf Mile Stakes, 12:36 p.m. ET

#2 Flower Point (8-1): She’s won every other race in six starts since June 2021 and is clearly sitting on a win after finishing third by a half-length in the Plenty of Grace Stakes. I joke, of course if only this game was that easy. Still, she has run exceptionally well in her last four starts for Hall of Fame trainer Shug McGaughey and picks up Eclipse Award-winning jockey Joel Rosario for this race after what looked like a terrific starting point to the season April 16 at Aqueduct in the Plenty of Grace. I also think a couple of the other contenders might be a bit overrated for one reason or another, so I like her chances to win at a price.

Race 7, Pat Day Mile Stakes Presented by LG&E and KU, 1:56 p.m. ET

#9 Trafalgar (20-1): When I looked over this race, I saw quite a few horses I knew for sure I had no interest in betting as well as a probable heavy favorite, #5 Jack Christopher (2-1), who has not raced in seven months. My instinct was to look for a bomb to light up the toteboard and I landed on Trafalgar. He won his second career start at this track and distance last October and added a win in December at Fair Grounds before back-to-back unplaced finishes at that New Orleans track in graded stakes on the Kentucky Derby trail. He’s been freshened since the Feb. 19 Risen Star Stakes presented by Lamarque Ford by trainer Al Stall Jr., who clicks at 38% for runners coming off a 61-to-180-day layoff and also wins at a high percentage in stakes races. Trafalgar has worked well for this race, and I expect him to enjoy cutting back to a mile here and run a big one.

Race 12, Kentucky Derby Presented by Woodford Reserve, 6:57 p.m. ET


#7 Crown Pride (20-1): I listed the Japanese invader as a value play because I think he will leave starting gate at lower than his 20-1 odds on the morning line given all of the buzz surrounding him. I never back the UAE Derby Sponsored By Mubadala winner – usually a complete toss for me – in the Kentucky Derby and I expect his odds to be lower than the morning line, so what gives? First and foremost, as always, is talent. I think he’s the best Japanese horse to compete in the Kentucky Derby and, probably, the best UAE Derby winner I’ve seen. I’ve also been very impressed with the way he’s acclimated, which is a big component for horses shipping in from Dubai, and how he has prepared for the race. Finally, as we saw in last year’s Breeders’ Cup and this year’s Dubai World Cup, Japan has been on roll internationally and Crown Pride appears to be a high-quality contender.


#8 Charge It (20-1): Toyota Blue Grass Stakes winner Zandon (#10) and White Abarrio (#15) are my top two selections for the Kentucky Derby. Given I like the latter coming out of his win in the Curlin Florida Derby Presented by Hill 'n' Dale Farms at Xalapa, I found my way over to also including Charge It on my exacta and trifecta tickets. I was a big fan of his early in the year and I like how he has trained in preparation for the Kentucky Derby after overcoming trouble in a runner-up finish, beaten by 1 ¼ lengths, in the Florida Derby. He’s been a little green and only has three races under his belt, but the speed figures say he fits and I believe in the ability of this colt by leading sire Tapit out of a half-sister to champion Will Take Charge. He has a chance to take a step forward in his fourth start of the year with five weeks of rest, and I expect him to be right in the hunt in deep stretch in the Derby.

newsletter sign-up

Stay up-to-date with the best from America's Best Racing!