NBC Sports analyst Drew Dinsick has identified his top double bet for the Kentucky Oaks and Kentucky Derby at Churchill Downs [1].

These selections are critical for bettors looking to capitalize on the high-stakes weekend in Louisville, where the success of a single trainer can influence the odds of multiple races.

Dinsick's primary recommendation for the Kentucky Oaks involves a filly trained by Chad Brown [1]. He said the horse's recent preparations were exceptional, stating, "We've got a Chad Brown filly who's been putting in phenomenal workouts" [1].

For the Kentucky Derby, Dinsick's top pick is a colt trained by the individual who won the Derby in 2025 [1]. This strategy relies on the momentum of a trainer who has already proven capable of winning the most prestigious race in U.S. horse racing.

Expert Jody Demling said the best double pick this year is the Chad Brown filly paired with the colt from the previous year's winning trainer [2]. Demling brings a history of success to these predictions, having previously secured a $1,682 superfecta win in 2025 [2].

The events take place over two days in Kentucky. The Kentucky Oaks is scheduled for Friday, May 1, 2026 [3], while the Kentucky Derby follows on Saturday, May 2, 2026 [3].

Both races are held at Churchill Downs, where the festivities draw international attention and significant wagering activity [3]. The combination of Brown's current form and the 2025 winning trainer's experience forms the basis of this specific betting strategy.

“"We've got a Chad Brown filly who's been putting in phenomenal workouts."”

The focus on a 'double bet'—linking the outcomes of the Oaks and the Derby—highlights a strategic approach to wagering that leverages trainer pedigree and current workout data. By pairing a trainer known for precision, like Chad Brown, with a trainer who has recently mastered the specific challenges of the Derby, analysts are attempting to mitigate the inherent volatility of three-year-old horse racing.