Analysis | Four tips to maximize your Kentucky Derby betting success


As the Kentucky Derby approaches, bettors often wonder how to maximize their chances of scoring a winning ticket. Blind luck isn’t the answer. Grab your racing form and let’s focus on some strategies to increase your success betting on the Run for the Roses.

Stay away from short-priced horses with red flags

The morning-line favorites in the Kentucky Derby rarely offer value. That value diminishes further when the favorites are marred by red flags. These 20 horses are being asked to navigate 1¼ miles for the first time, and to win the race requires a combination of peak effort and the right circumstances.

This year’s morning-line favorite, Fierceness (5-2), has struggled out of the gate at times and has a clear pattern of producing his A game followed by a clunker. Since his latest effort, a win in the Grade I Florida Derby, was sensational, it is not far-fetched to imagine he won’t have his best race this time around.

Sierra Leone, the second choice on the morning line (3-1), drew post No. 2, which last produced a winner in 1978 (Affirmed). The inside post is tough for this race, because horses near the rail have to push hard toward the front to avoid being blocked by a large field with 19 other horses. That often means extra energy must be expended earlier than is desirable. That trend disproportionately affects closers such as Sierra Leone, since they are used to conserving energy for a late kick toward the finish line. We should also discount Sierra Leone’s latest win in the Grade I Blue Grass. He was gifted a fast pace and took advantage, yet he couldn’t do better than par for his final speed figure. I’ll be staying away from both Fierceness and Sierra Leone at the top of my tickets.

Identify which horses will be helped or hindered by Saturday’s expected pace

Pace makes the race, and lately the early pace in the Kentucky Derby has been faster than usual. This means front-runners are less desirable than horses that sit further back off the pace.

To help label horses, analyst Bill Quirin introduced a system based on past performances at the first call, which is the ¼-mile mark in sprints and ½-mile mark in routes, or longer races. The running styles are denoted as front-runners (on the lead), stalkers (one or two lengths off the lead), pressers (more than two lengths off the lead at the first call) and closers (near the back of the pack). In this race, there could be as many as seven front-runners, all needing to secure the lead to ensure their best performance. With this many horses vying to be a part of the first flight, it’s best to discount virtually all of them in favor of the pressers and closers.

Create a value line and bet accordingly

Once you have your list of contenders, it is time to ballpark their chances of winning the race. Only then will you know whether your risk is justified by the potential reward. If you think a horse has a 25 percent chance to win but that horse is a 2-1 favorite, then it is not worth the risk. On the other hand, the same horse at 6-1 odds would offer a terrific wagering opportunity.

Don’t think you are savvy enough to estimate a horse’s chances of winning a race? Use Marc Cramer’s contender line as your guide. He proposed ranking horses and assigning prefixed probabilities to them. If you think only one horse is a true contender then you must demand even money or better to make a wager. Have two horses you like? Your top pick must be 2-1 or better and your second choice 5-2 or better. Three contenders in the field would require at least 3-1 on your top choice, 9-2 on the second choice and 6-1 on the third choice.

My top contenders for this year’s Kentucky Derby are No. 7 Honor Marie followed by No. 4 Catching Freedom, No. 1 Dornoch and No. 8 Just A Touch. Since those are four contenders, they would require odds of 4-1, 5-1, 8-1 and 9-1, respectively, for me to place a win wager on Saturday. Bet any contenders that reach the proper threshold.

Consider different bets — including exotics

The staple of any horse bettor is the win wager, but for special events such as the Triple Crown, it is worth exploring exotic wagers such as trifectas (in which you must correctly select the first three finishers in order) and superfectas (in which you correctly select the first four runners in order) because the payouts are sometimes enormous.

A streamlined approach is always best, and you should avoid playing too many combinations. One of my favorite strategies to play the trifecta is to key a horse (it should not be a short-priced entry) in each spot — win, place and show — with three other contenders, which we will label A, B and C. You would win if your “key” horse finishes anywhere in the top three, along with two of your other three contenders. The three tickets look like this and cost $3 each if the minimum trifecta ticket is 5o cents.

  • Key with A,B,C with A,B,C
  • A,B,C with Key with A,B,C
  • A,B,C with A,B,C with Key

Don’t have a key horse? You could use two of your top contenders at the front with some other possibilities in the place and show spots such as A,B with A,B,C with A,B,C,D,E. A ticket like this would also cost $6 if the trifecta carries a minimum of 50 cents.

The minimum for superfecta tickets on Kentucky Derby day is $1, so the combinations can get expensive quickly. If you have a limited bankroll you must find a horse or two you are comfortable singling to keep the costs from escalating. Mike Hogan of the Daily Racing Form highlighted a few superfecta strategies I use often, with one called the “triangle” ticket that could work for limited budgets. You key your main horse with three other contenders on one ticket and expand the number of possibilities for the fourth spot on another ticket, giving you a chance to hit the superfecta twice. It looks like this:

  • A with B,C,D with B,C,D with B,C,D for $6
  • A with B,C with B,C,D with B,C,D,E,F for $12

Here’s how I would structure my trifecta and superfecta tickets in this year’s race.

I would use No. 7 Honor Marie and No. 4 Catching Freedom at the front with No. 1 Dornoch, No. 2 Sierra Leone, No. 3 Mystik Dan and No. 8 Just A Touch in the place and show spots.

If your bankroll permits, I would expand the superfecta’s final slot to include the two horses from Japan — No. 10 T O Password and No. 11 Forever Young — plus No. 14 Endlessly, No. 15 Domestic Product and No. 16 Grand Mo The First.

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