Racing Roundtable: Kentucky Derby 150 and Oaks preview

April 24th, 2024

The Racing Roundtable convenes to preview the 150th running of the Kentucky Derby (G1) and the Kentucky Oaks (G1), including top picks and handicapping tips.

Who is your top Kentucky Derby pick at the moment?

James Scully: Sierra Leone. The late runner has progressed nicely in a pair of three-year-old starts, getting up in the final jumps to secure a narrow win in a deep Risen Star (G2) and rolling to a 1 1/2-length decision in the Blue Grass (G1), and the Chad Brown-trained colt appears likely to receive a favorable set up in the Kentucky Derby, with a hot and contested pace projected. He must load better than he did in the Blue Grass, but Sierra Leone appears set for a top showing. 

Vance Hanson: I have all the respect in the world for Fierceness, who is clearly the fastest on paper, and Sierra Leone, who has looked tremendous as well, but I'm usually looking for more value in the Derby. Right now, I'm gravitating toward Catching Freedom, who's done little wrong and figures to be in the 10-1 range. Although third best to Sierra Leone in a key edition of the Risen Star, he was sensational when producing a last-to-first rally in the Louisiana Derby while not getting nearly as much pace help there as Sierra Leone did in the Blue Grass.

He'll have to work out a trip, like they all have to, but Catching Freedom really hasn't made many mistakes and has winning experience over the Churchill surface to boot.

Ashley Anderson: Chad Brown trainee Sierra Leone has been my top pick for quite a while and I have no reason to shy away now, other than his potential post-time price. The Gun Runner colt is 3-for-4, with his lone loss a nose second in his second career start in the Remsen (G2) at age two. He added blinkers after that effort and has shown greater focus and a strong closing kick in his last two, including the Blue Grass (G1), where he went from back of the pack to first.

If looking for value, Brad Cox pupil Catching Freedom has a similar late burst and posted a 101 Late Pace rating last out when winning the 1 3/16-mile Louisiana Derby (G2), and Honor Marie is another late runner who has two victories from three starts at Churchill. Wood Memorial (G2) hero Resilience is an early runner who could factor as well and recorded a 104 Brisnet Speed figure last out, the second-highest last-out speed figure among the field.

Who has the best chance to win the Kentucky Oaks?

JS: Just F Y I. Unbeaten from three starts last year, the champion two-year-old filly made a belated seasonal debut in the Ashland (G1) and experienced a wide trip off the far turn rallying for second. She looks poised to move forward in the second start, recording a strong five-furlong bullet work at Churchill Downs Tuesday, and the well-built daughter of Justify has the positional speed to make her own trip.

VH: At this early stage I've debated whether to side with Power Squeeze or Leslie's Rose. Power Squeeze will be the better price, but Leslie's Rose might simply be the better horse after a huge win in the Ashland (G1). After demonstrating some greenness when taking some dirt to the face in the Davona Dale (G2), Leslie's Rose handled a similar situation more like a pro at Keeneland and romped to a three-length win.

Granted, she had a recency edge in the Ashland over champion Just F Y I, who figures to benefit from the run and has reportedly been working very well. However, Leslie's Rose is really getting good now and hails from a barn that has won the Oaks with such standouts as Ashado, Rags to Riches, Princess of Sylmar, and Malathaat. Todd Pletcher can tie Woody Stephens and his mentor, D. Wayne Lukas, for most Oaks wins (5) by a trainer if Leslie's Rose can get the job done.

AA: Just F Y I is my top pick, and I'm hopeful her three-length second last out in the Ashland (G1) will keep her price a bit higher at post time of the Oaks. The Breeders' Cup Juvenile Fillies (G1) upsetter clocked a 100 BRIS figure two back in her two-year-old finale, but her training was interrupted as a three-year-old when she drew a fever that forced her to scratch from the Davona Dale (G2) at Gulfstream. She raced instead in April's Ashland, where she got floated five wide entering the lane and ran on willingly to place late. She can improve second off the layoff for Bill Mott and put in a bullet work at Churchill April 22.

Anything noteworthy from morning works or other info you watch for before making final Derby/Oaks wagers?

JS: Sierra Leone was out for the first time at Churchill Downs Monday and Fierceness took his initial tour of the oval Tuesday. The two big horses are on the grounds, and we’ll get the chance to see both work under the Twin Spires this weekend.

After receiving positive reviews for his five-furlong work last Saturday, Catching Freedom continues to make a favorable impression in his morning gallops. He concluded his juvenile campaign with a fourth versus allowance foes and came back to capture the Smarty Jones S. at Oaklawn Park on New Year’s Day, registering a modest 89 Brisnet Speed rating for an early-season event that has had no impact on the Kentucky Derby. Catching Freedom wasn’t considered one of the best three-year-olds in Brad Cox’s barn at that point, overshadowed in morning works at Fair Grounds by stablemates Just a Touch, Timberlake, Nash, and others, but the Louisiana Derby (G2) winner has changed the narrative.

VH: Jeff Ruby (G3) winner Endlessly, who has not yet raced on dirt, appears to have been struggling with the surface in recent works at Churchill Downs. In his most recent morning drill on Saturday, Endlessly couldn't keep up with a recent maiden winner he was working with and didn't gallop out well by comparison.

Trainer Michael McCarthy was keen on targeting the American Turf (G2) with Endlessly after the colt's win at Turfway and would surely prefer to stick to that original plan. The fact he hasn't been officially removed yet from Derby contention suggests there might be a difference of opinion among his connections on where to run. Based on what we've seen from him at Churchill, Endlessly deserves to run where he best fits, and that's arguably the American Turf. He's a big fade for me, even in the exotics, if he starts in the Derby.

AA: Track Phantom was working out with blinkers this week, and equipment changes can be a valuable tool when handicapping ahead of the Derby or Oaks. While I'm still not high on Track Phantom's chances after he failed to reach the winner's circle in his last two starts since stretching out beyond 1 1/16 miles — and he had the early lead in both of those recent tries — blinkers could help him stay focused in the stretch as late runners challenge him.

Last year in the Kentucky Oaks, 10-1 shot Pretty Mischievous added blinkers in the 1 1/8-mile test. One start prior, she drove clear in upper stretch but succumbed to Southlawn charging at the sixteenth pole in the Fair Grounds Oaks (G2), where Pretty Mischievous ultimately finished second. I noted ahead of the Oaks that trainer Brendan Walsh won at a high percentage when adding blinkers for the first time, and sure enough Pretty Mischievous improved in her Kentucky Oaks effort, holding off a challenge from Gambling Girl in the final sixteenth on Churchill's main track. Unfortunately, I backed the runner-up in that race, but going forward I certainly learned to be extra mindful of those equipment changes, especially when the trainer is known to do well with them.