Most years, I like to take a look through the entire cards for the Longines Kentucky Oaks on Friday and the Kentucky Derby Presented by Woodford Reserve on Saturday for value bets and live longshots. The two feature races alone this year, however, feature so many intriguing double-digit longshots that I decided to make them the focus and dig deeper into the value to be had in the $1.5 million Oaks and $5 million Derby.

Friday, May 3, Churchill Downs, $1.5 million Longines Kentucky Oaks, 5:51 p.m. ET

My initial view of the 2024 Kentucky Oaks was that it was pretty wide-open and could be anyone’s race. That perspective stands … provided the weather complies and the main track is fast on Oaks day. The forecast indicates that might be unlikely to happen with rain on Oaks day with scattered thunderstorms in the forecast for both Friday and Derby day on Saturday. If the Oaks is held on an “off” track on Friday – meaning good, muddy, sloppy, wet-fast, sealed, etc. – because of rain, favorites #8 Tarifa (7-2), #13 Just F Y I (9-2), and #14 Leslie’s Rose (4-1) will be formidable. All have posted wins on “off” tracks and boast very strong Tomlinson numbers, which Daily Racing Form uses to make an educated guess how racehorses will handle wet tracks based on performance of the horse’s sire and broodmare sire’s progeny on “off” tracks.

Factoring weather into the equation, let’s take a quick look at all of the Oaks entrants at 10-1 odds or higher on the morning line in search of value in terms of betting the race. For this exercise, I also didn’t consider #5 Thorpedo Anna (5-1) and #11 Ways and Means (5-1) due to the odds.

1. Tapit Jenallie (SCRATCHED): She could move up a bit with an “off” track, but she was 7 ¼ lengths behind Thorpedo Anna in the Grade 2 Fantasy Stakes and does not look fast enough. NOTE: Tapit Jenallie was scratched from the race on Thursday and will not compete in the Kentucky Oaks.

2. Gin Gin: (30-1): Another who gets a slight boost with a wet track … and another who does not appear to be fast enough on paper to be a real threat.

Where's My Ring (Eclipse Sportswire)

3. Where’s My Ring (15-1): Where do I sign up for 15-1 on an improving 3-year-old filly coming off a dominant 4 ¼-length win at this distance in the Gazelle Stakes? Count me in! (Note: my enthusiasm would be tempered a bit on a wet track.)

4. Regulatory Risk (20-1): The Gazelle runner-up might be an underlay because of the high-profile trainer-jockey tandem of Chad Brown and Jose Ortiz. Eligible to run well but I much prefer the Gazelle winner (see above).

6. Lemon Muffin (30-1): Square price on the Honeybee Stakes winner if you can forgive a dud in the Fantasy Stakes, beaten 10 ¾ lengths, in her most recent start. Two rallying seconds at Churchill as a 2-year-old a reason for optimism.

7. Fiona’s Magic (30-1): Was first or second in each of her first five races before she was distanced (beaten by 40 or more lengths) in the Grade 2 Gulfstream Park Oaks Presented by FanDuel TV. Trainer Bo Yates said the post-race scope brought up a ton of mucous, indicating she was sick. Looks much more appealing if you draw a line through that race.

9. Everland (30-1): Has never raced on dirt, so she’s a true wild card. Her 447 Tomlinson rating for a wet track is the highest of the 14 entrants and two also-eligibles, so she might be worth using if it rains.

10. Into Champagne (30-1): She another who looks more playable on a wet track with a stakes win on a sloppy main track and the second-highest Tomlinson rating (445) for a wet surface. On a dry (fast) main track, I much prefer others.

12. Power Squeeze (12-1): I doubt the morning-line odds will hold for a filly who has won four straight, including three stakes wins this year. Absolutely good enough to win and fast enough to work out a good trip.

15. Our Pretty Woman (15-1): She was on the also-eligible list but drew into the race with the defection of Tapit Jenallie. Our Pretty Woman is my best bet of the day May 3 at Churchill. She has great speed and is a threat to lead from start to finish coming off a second to Tarifa in the Fair Grounds Oaks Presented by Fasig-Tipton. She’s also improved in each of her three starts for Hall of Fame trainer Steve Asmussen and is 2-for-2 on a wet track.

16. Candied (20-1): Another who would be a serious player should she get two defections and draw into the race. She ran fourth in the Grade 1 Central Bank Ashland Stakes in her first start in six months and should improve if she draws into the race. A wet track should not be an issue.

Top longshot: Our Pretty Woman

Other legit longshot win candidates (in order of preference): Where’s My Ring, Power Squeeze, Candied

Bombs away for exactas/trifectas: Fiona’s Magic, Lemon Muffin

Saturday, May 4, Churchill Downs, $5 million Kentucky Derby Presented by Woodford Reserve, 6:57 p.m. ET

For evaluating the Kentucky Derby longshots, let’s shift the goalposts to entrants with odds of 15-1 or higher on the morning line. That eliminates from this discussion morning-line favorite #17 Fierceness (5-2), Toyota Blue Grass Stakes winner #2 Sierra Leone (3-1), Twinspires.com Louisiana Derby winner #4 Catching Freedom (8-1), Blue Grass Stakes runner-up #8 Just a Touch (10-1), and UAE Derby Presented by Atlantis The Royal winner #11 Forever Young (10-1).

The beauty of the Kentucky Derby as a betting race is that you have the opportunity to bet improving runners, often coming off a career-best race, at massive odds, so please don’t let me talk you out of a longshot you like. Handicappers and bettors all value different things and in the Derby, you could be richly rewarded for a contrarian opinion.  

Rain also is a possibility, so that is a part of the equation, although Bob Ehalt provided more detail on which runners would benefit from an “off” (wet) track in a separate blog post. So without further ado, let’s take a look at the longshot contenders for the 2024 Kentucky Derby.

1. Dornoch (20-1): The full-sibling to 2023 Kentucky Derby winner Mage has run well in two tries on “off” tracks, including a win over morning-line second choice Sierra Leone in the 2023 Remsen Stakes. The inside post in a 20-horse field was a brutal draw and he enters the Derby off the worst start of his career, so I’m looking elsewhere.

3. Mystik Dan (20-1): He’d probably benefit as much as any of the Derby entrants if the track came up wet on Saturday. I didn’t like his Arkansas Derby third-place finish, but he romped on a muddy track with a huge speed figure in the Southwest Stakes. Worth a play if the rain comes.

5. Catalytic (30-1): Has only a maiden win to his credit in three starts. Picking up jockey Jose Ortiz helps and he has tactical speed, but consider me skeptical he’s ready for this challenge.

Just Steel (Eclipse Sportswire)

6. Just Steel (20-1): Based on speed figures, he jumps off the page as a candidate to outrun his odds for Hall of Fame trainer D. Wayne Lukas. I plan to use the Arkansas Derby runner-up pretty heavily in my exotic bets.

7. Honor Marie (20-1): He seems to be the “buzz” horse on the Kentucky Derby backstretch, so he’s training well and there is a good chance his odds come down a bit. He’s coming off a quality second to Catching Freedom in the Twinspires.com Louisiana Derby, beaten only a length, and offers much more appealing odds. Also owns two wins and a second in three starts at Churchill. A win candidate and a must use in exotics for me … unless it rains.

9. Encino (SCRATCHED): A winner of three straight, including a front-running win in the Stonestreet Lexington Stakes that allowed him to qualify through the back door for the Kentucky Derby. I’m a big fan of this 3-year-old and he’s improving, but it’s a tough spot on three weeks of rest. NOTE: Encino was scratched from the race on Tuesday and will not compete in the Kentucky Derby.

10. T O Password (30-1): He’s 2-for-2 in Japan but he was all out to hang on going about 1 1/8 miles in the Fukuryu Stakes against much lesser competition than what he’ll face here in his third career start. I much prefer his more-experienced countrymate Forever Young’s chances to win the Derby.

12 Track Phantom (20-1): With his speed and a couple of seconds on “off” tracks, he’d move up a bit if it rains on Derby day. He’s fast enough to be in the hunt in the stretch, but he faded late in his last start at 1 3/16 miles and it’s tough to envision that changing going farther here.

13. West Saratoga (30-1): He’s a game colt and a great story, but I just don’t think he’s fast enough to be a serious threat.

14. Endlessly (30-1): One of the more talented 3-year-olds in the field with five wins in six starts, but he’s never run on dirt and his trainer seemed to prefer racing him on grass Derby weekend rather than the first jewel of the Triple Crown.

15. Domestic Product (30-1): My hunch is he will be flying late after he was, by a significant margin, the fastest finisher of his final three furlongs and last eighth of a mile in his final prep race. Check out our Derby Data blog for more details. Love his chances to spice up the exacta or trifecta at big odds. Rain would dampen my enthusiasm.

16. Grand Mo the First (50-1): His third by a neck in the Lambholm South Tampa Bay Derby offers some reason for optimism, but he was 16 lengths behind Fierceness and 2 ½ lengths behind runner-up Catalytic in the Curlin Florida Derby Presented by Hill ‘n’ Dale Farms at Xalapa. Not for me.

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18. Stronghold (20-1): Enters off back-to-back wins in the Sunland Park Derby and Santa Anita Derby, so 20-1 on the morning line is a terrific price. He’s a fighter with tactical speed but I did not love how slowly they finished in the Santa Anita Derby. Give him a longer look if it rains as his Tomlinson (422) for a wet track indicates he’d relish an “off” surface.

19. Resilience (20-1): Would have preferred a better post position, but he has the speed to get decent early position and took a nice step forward with the addition of blinkers in the Wood Memorial Stakes Presented by Resorts World Casino. He’ll need to take another big step in terms of speed figures, but this well-bred colt is a win threat for Hall of Fame trainer Bill Mott.

20. Society Man (50-1): Adding elite jockey Frankie Dettori, one of the best ever at his craft, adds to the appeal, but the post-position draw did him no favors. He’s improving but I’m not sure he’s fast enough.

21. Epic Ride (30-1): Has tactical speed and has never been worse than third in five starts. Tough to see the Blue Grass third-place finisher making up 5 ¼ lengths on Sierra Leone after he drew into the race with the defection of Encino, but he could at least be in the mix near the top of the stretch.

22. Mugatu (30-1): Unplaced in three tries against stakes competition and unplaced in three starts on dirt main tracks. He also needs two defections to get in. Tough to make a compelling case for him.

Top longshot: Honor Marie

Legit longshot win candidate: Resilience

Bomb’s away for exactas/trifectas: Just Steel, Domestic Product