THIS WEEK IN RACINGRace Date: 08/31/2025

Jockey Club Gold Cup Picks

Saratoga, Race 5, Jockey Club Gold Cup (G1), Post Time-1:45 PM ET

3
Sierra Leone
2
Highland Falls
1
Disarm
4
Mindframe

The Jockey Club Gold Cup (G1) drew a particularly strong field this year with eight graded stakes winner including four Grade 1 victors. The key dynamic this year is the pace as there are several horses who prefer to sit forward trips starting with #4 Mindframe (2/1) who will want to avoid getting trapped inside as all the dominant speed to the outside. Horses like #8 Antiquarian (12/1), #7 Phileas Fogg (15/1), and #6 Contrary Thinking (50/1) all possess good early speed. Above all, you would expect Contrary Thinking is entered again to ensure a strong pace for his stablemate, #3 Sierra Leone (8/5) just as he did in the Whitney (G1). With a strong pace and the 1 ¼ mile distance, the race seems custom made for Sierra Leone to get the victory.

The winner of the Whitney (G1) has always been an imposing figure when he walks in the paddock as you see why he went for $3.2 million as a yearling at the Fasig-Tipton sale in 2022. He is a physically imposing horse who has had his quirks over the years from lugging in to losing focus. However, he seems to have grown out of those as he has run straight and shown more professionalism in the stretch in recent starts. He is a horse that has always appreciated more distance and if he gets a strong pace then he is hard to get past with those big, powerful strides coming down on the outside. Additionally, jockey Flavien Prat appears to have figured out how to ride him more effectively over the last few races as he moves the deep closer into contention around the turn. He does not leave himself too much to do turning for home anymore as he is often within a couple lengths of the lead once they straighten for home. Several horses in this race do not want any part of the 10-furlong distance and Prat should easily be able to maneuver the horse through the field so that he has a clear run at the beleaguered frontrunners at the top of the stretch. Sierra Leone excised any demons he may have had at Saratoga by winning the Whitney (G1) as he was previously winless at The Spa and now he feels like a horse that is on a collision course with Sovereignty in the Breeders’ Cup Classic (G1).

The winner of last year’s Jockey Club Gold Cup, #2 Highland Falls (5/1) is a serious horse and one that I believe should be considered as an upset candidate. The son of Curlin clearly loves distance and is rounding into exceptional form this year. He was a late-developing horse for trainer Brad Cox as a three-year-old but stepped up to run some big efforts last year, most notably at The Spa where he pestered Arthur’s Ride into submission before pulling away to win this race. He did not run well in the Breeders’ Cup Classic (G1) and went to the bench for a prolonged stretch before returning to win an allowance optional claiming race at Belmont at Aqueduct. Based off that one effort, Cox and Godolphin opted to send the horse directly to the Whitney (G1) where he ran a strong second and was assigned a career-best 107 Beyer Speed Figure (BSF). The horse is now third back in the form cycle and should sit an ideal trip behind the early pace, but much closer than Sierra Leone so he will have the jump on the Whitney (G1) winner. It’s possible he could turn the tables, but what feels certain is that he will run another strong effort at a bit of a price.

Another horse that ran well in the Whitney (G1) is #1 Disarm (15/1) for trainer Steve Asmussen. The son of Gun Runner has always been a horse held in high regard but has failed to break through on the biggest stages as his signature win to this point is in the Matt Winn (G3) two years ago. However, he teases with talent such as when he finished second to Arcangelo in the 2023 Travers (G1) or last time out when he made a long, sustained bid from 11 lengths back to close for third against Highland Falls and Sierra Leone. He just does not win enough for my liking, but jockey Joel Rosario stays on for the second straight race and at 15/1 on the morning line, he is a horse that feels like to crack into the top three based off the pace dynamics and distance.

Finally, we arrive at #4 Mindframe (2/1) for trainer Todd Pletcher and owner Mike Repole. The winner of the Churchill Downs (G1) and Stephen Foster (G1) has only lost twice in his career and both times were as a three-year-old when he got the lead against Dornoch late only to relinquish it in the final strides. He has come back as a four-year-old and bested horses like Nysos, Banishing, Book ‘em Danno, First Mission, and Sierra Leone. The issue with Mindframe is whether he can comfortably rate off the pace from an inside position as he should be able to secure the rail, but jockey Irad Ortiz Jr. will need to decide about whether to go to the front or sit behind horses like Phileas Fogg who could try to cross and clear in front of him. The other question is the distance. The son of Constitution is likely best at nine furlongs but ran a good race going 1 ¼ miles in last year’s Belmont. It was only his third career start and his greenness lugging out in the stretch shouldn’t be mistaken for an inability to get the distance. However, he is unlikely to get as perfect of a trip as he got in the Stephen Foster (G1) where he cruised over Sierra Leone. He is coming off a career-best BSF and I think it is fair to question whether he can reach another level on Sunday to win this race. I think at nine furlongs he is one of the few horses that can beat Sierra Leone, but at 10 furlongs the 2024 Breeders’ Cup Classic Champ will be hard to beat.

How I’m playing it: You could easily make the argument to single Sierra Leone in this leg of any sequence you are playing, especially since the Early P5 is filled with some competitive maiden races where you would want to spread. Due to the pace dynamics and distance in the Jockey Club Gold Cup (G1), I feel comfortable singling a horse that I have been a critic of for most of this year, but there is no denying that when he gets his setup, he is nearly impossible to beat. Sierra Leone is a horse I will single, and I’d attack this race in vertical wagers to make some additional money by using the combination of Highland Falls and Disarm underneath.