The 150th running of the Kentucky Derby takes place on Saturday, May 4 with 20 horses competing in the Run for the Roses. Bettors love the Kentucky Derby because the odds offer opportunities for longshots to finish in the money. 

Fierceness and Sierra Leone will enter Saturday’s race as the betting favorites but that’s not always a good omen in the Kentucky Derby. I like one of those horses but I’m fading the other. 

If you are not familiar with horse racing and just pop up to bet the Derby, picking the best options in such a crowded field can be daunting. Here is how I see the race unfolding, including a 20-1 longshot I believe will finish in the money. 

Kentucky Derby betting strategy: How to wager on the 150th Run for the Roses

Betting odds are as of Friday, May 3

WIN: No. 4 Catching Freedom (8-1)

This is one of the tougher Kentucky Derbys in recent memory to handicap because I think at least half the field could end up in the winner’s circle. The horse I like the most though is Catching Freedom. 

Catching Freedom has won three times in five career starts and is coming off an impressive victory in the Louisiana Derby. He’s also the only horse in the field that has seen his Beyer Speed Figure improve by five points or more in every start.

What does that mean? It means Catching Freedom keeps getting faster and enters the Kentucky Derby running at the top speed of his career. 

There are a lot of horses who will want to get out in front and use their early speed. I like Catching Freedom because I expect jockey Flavien Prat to sit in the middle of the pack and close late. If the speed is there, Catching Freedom should run past horses losing steam down the stretch. 

Prat won the Kentucky Derby in 2019 and trainer Brad Cox took home the win in 2021. There is a lot to like about Catching Freedom and I think he offers the best combination of speed and value in this race. 

PLACE: No. 3 Mystik Dan (20-1)

When it comes to the Kentucky Derby, I like betting on speed and Mystik Dan has plenty of it. He owns one of the top Beyer Speed Figures in the field when he blazed a 101 in the Southwest Stakes. Mystik Dan has finished in the money in four of his six career starts. I think that trend continues in the Kentucky Derby. 

Some may be concerned because Dan followed up his impressive Southwest Stakes win with a third-place finish in the Arkansas Derby. However, he got squeezed early in that race and didn’t have the most favorable trip. I thought Mystik Dan showed promise by overcoming some early obstacles to finish third in that race. 

Sometimes where a horse finished can be misleading. If you watch the Arkansas Derby, Mystik Dan was surging late. He draws pole position three in the Kentucky Derby. I think the fact that he got caught in the wash early and was able to still close strong his last time out is a good omen for a speed race like the Derby. 

Not many people are talking about Mystik Dan. He’s not one of the sexy longshot picks this year. I like the fact that he’s being overlooked. Dan is one of the fastest horses in the race and if jockey Brian Hernandez Jr. can successfully navigate through traffic, watch out. Mystik Dan has the makeup of a horse to pull a Kentucky Derby upset. 

SHOW: No. 2 Sierra Leone (3-1)

Sierra Leone and Fierceness have gone back and forth as the betting favorite this week. My guess is Sierra Leone will close with the shortest odds because a lot of people love this horse, and for good reason. 

Legendary trainer Chad Brown is still searching for that elusive Kentucky Derby win and he might finally get it on Saturday with this horse. Sierra Leone has recorded three firsts and a second in four career starts and has already beaten top competition like Catching Freedom and Just a Touch. The horse has tremendous late speed and will be dangerous if he doesn’t get boxed in early from the two hole. 

Catching Freedom and Sierra Leone want to run a similar race where they get out of traffic early, sit back, then charge down the stretch. I give Catching Freedom a slight edge because I hate Sierra Leone drawing the two hole, but this is a talented horse who could blow by the field if he gets a good ride. I’ll have Sierra Leone in most of my exotic bets on Saturday. 

Picks

Catching Freedom (8-1) to win

Mystik Dan (20-1) win, place, show

Catching Freedom, Mystik Dan, Sierra Leone trifecta box