Betting the 2026 Kentucky Derby: Chief Wallabee’s recent form could hold the key

With fields as big as 20 horses, the Kentucky Derby is generally regarded as the biggest handicapping puzzle in North American racing. Handicappers tend to agonize over this race, and with good reason. No horse is guaranteed a good trip, and the unexpected can and will happen.

The uncertainty of the race can lead bettors to go to extremes, which is rarely a good approach. For example, you can “spread” your bets, including too many horses on your tickets. This approach doesn’t guarantee a winner, and the amount of money you invest can cut down on potential profits.

In 2019 I was asked by a media outlet how I would recommend betting the race with a bankroll of $100. Wiseguy that I am, I suggested a $1 denomination 10-horse exacta box, with the ticket costing $90. The last horse I eliminated from that bet was Country House, who(because of the disqualification of Maximum Security for interference) was put up for the win at odds of 65-1, triggering a $1500 exacta.

Oh, well… In 2000, I went in the opposite direction. I made one bet on the race, and it only cost $42. It was a year when the favorite was clearly the best horse.