Ryan Dickey: Wagering Suggestions for KY Oaks & KY Derby

By Ryan Dickey:

It’s finally here–the145th running of the Kentucky Derby is upon us and there are plenty of reasons to dream of huge payouts as the “run for the roses” appears to be a wide-open affair this year.

Every year, I place some bets on the Derby that have become traditions for me–my “one by three by four by ALL” Derby pick-4,my “ALL over x” exacta, a five horse trifecta box and a stab at the Derby superfecta as wagers I make yearly. I also dabble in the Oaks/Derby double as well as the Oaks/Old Forester/Derby pick-3.

I’ll save the long explanations of “why” I’m betting the way I’m betting, and spend more time explaining the “how” to bet what I’ll be betting.

First of all, by pick to win the Kentucky derby is #16 GAME WINNER. The Bob Baffert trained Candy Ride colt will be ridden by Joel Rosario. He is owned by Gary and Mary West, who are looking to win their very first Kentucky Derby.

I’ll have a WIN bet on Game Winner. How much you want to bet on him to win is up to you. He is listed as the 9/2 favorite on the revised morning line following the scratch of Omaha Beach from the race.

The horse I will bet to SHOW in the Kentucky Derby is #10 CUTTING HUMOR. Trained by Todd Pletcher, the First Samurai colt will be piloted by Corey Lanerie. Starlight Racing owns Cutting Humor, the winner of the Sunland Derby. He is 30-1 on the revised morning line.

Those are the only two straight bets I will be playing.

Wagers stemming from the Kentucky Oaks will focus on the race favorite and most-likely winner #4 BELLAFINA. My Oaks/Derby double will single Bellafina to #2 TAX, #5 IMPROBABLE, #8 TACITUS, #10 CUTTING HUMOR and #16 GAME WINNER. A $2 Oaks/Derby double would cost $10. (4/2,5,8,10,16)

Assuming Bellafina wins the Kentucky Oaks, the double payout should net a positive return, even if Game Winner wins the Derby–it won’t pay a ton, but it should cover the four losing wagers.

My play for the Oaks/Old Forester/Derby pick-3 will add these two other Oaks contenders with #4 BELLAFINA– #5 FLOR DE LA MAR and #14 RESTLESS RIDER. I will single #12 BRICKS AND MORTAR in the Old Forester Turf Classic. In the Derby, play the five selections from the Oaks/Derby double (2,5,8,10,16) and add these three horses: #1 WAR OF WILL, #6 VEKOMA, and #13 CODE OF HONOR. A $1 pick-3 ticket three by one by eight will cost $24. (4,5,14/12/1,2,5,6,8,10,13,16)

On Derby day, the pick-4 leading into the big event starts in race 9, the American Turf Stakes. I will be using four runners here. Every year I play this pick-4 and single one race, bet ALL in the Derby and go three deep in one and four deep in the other. A fifty cent ticket like this costs $120.

The four runners I will be using in the American Turf Stakes are: #1 A THREAD OF BLUE, #2 SOCIAL PARANOIA, #5 SEISMIC WAVE and #10 HENLEY’S JOY.

The second leg of the Derby pick-4 is race 10, the Pat Day Mile. I’ll be using three horses in this leg. Those horses are: #2 MARKET KING, #4 MR MONEYBAGS, #7 MR. MONEY and #10 INSTAGRAND.

In the Old Forester Turf Classic, I’ll again be singling Chad Brown’s #12 BRICKS AND MORTAR. He’s the easiest of winners on the first Saturday in May and should be treated as such–a “bet it and forget it” single in multi-race bets.

Should we win the first three legs of the pick-4, we’ll have an automatic winner, as we are betting ALL in the Kentucky Derby. Any horse that wins the Derby will give us a payout. Again, the 50 cent bet 1,2,5,10 with 2,4,7,10 with 12 with ALL costs $120.

In the Derby itself, I’ll be playing an exacta with ALL over #2 TAX. A $2 exacta All/2 will cost $38 is twenty horses go to the gate. Any scratches from this point on will only lessen the cost of the ticket.

I will be boxing five Derby horses in the $1 trifecta. This ticket will cost $60. The five horse I’m using in the trifecta are: #2 TAX, #6 VEKOMA, #8 TACITUS, #10 CUTTING HUMOR and #16 GAME WINNER.

In the $1 Derby superfecta, I’ll key two horses on top, and play five horses in the third spot and seven in the fourth position.

My two keys are #8 TACITUS and #16 GAME WINNER. Those horses have to finish first and second to have a chance to hit the superfecta. It’s a VERY risky bet–but we will be rewarded extremely handsomely should those two come in 1-2 and we catch the third and fourth place finishers.

The horses in the third spot in the superfecta are: #2 TAX, #6 VEKOMA, #10 CUTTING HUMOR, #13 CODE OF HONOR and #19 SPINOFF.

The horses in the final spot of the superfecta will be: #2 TAX, #5 IMPROBABLE, #6 VEKOMA, #7 MAXIMUM SECURITY, #10 CUTTING HUMOR, #13 CODE OF HONOR and #19 SPINOFF.

Again, the 8,16/8,16/2,6,10,13,19/2,5,6,7,10,13,19 $1 superfecta will cost $60.

I don’t expect anyone to play every single one of these bets. This is what I will be doing on Saturday. I very much hope that every single wager I suggest here is a winner, and that I need an armored truck to leave the racetrack on Saturday. For convenience, I’ll list the plays in bold below, and remember, I’m using the MINIMUM amount per bet unless otherwise noted. How much you bet personally is up to you.

Best of luck!

SUGGESTED WAGERS (in chronological order):

FRIDAY, MAY 3, Race 11 (approx 6:12 pm ET), $2 OAKS/DERBY DOUBLE: 4 with 2,5,8,10,16 ($10)

FRIDAY, MAY 3, Race 11, $1 OAKS/OLD FORESTER/DERBY PICK-3: 4,5,14 with 12 with 1,2,5,6,8,10,13,16 ($24)

SATURDAY, MAY 4, Race 9 (approx 3:37 pm ET) 50-cent PICK-4: 1,2,5,10 with 2,4,7,10 with 12 with ALL ($120)

SATURDAY, MAY 4, Race 12 (approx 6:50 pm) WIN bet on #16 GAME WINNER


SATURDAY, MAY 4, Race 12 EXACTA bet ALL over 2

SATURDAY, MAY 4, Race 12 $1 TRIFECTA BOX 2,6,8,10,16 ($60)

SATURDAY, MAY 4, Race 12 $1 SUPERFECTA 8,16 over 8,16 over 2,6,10,13,19 over 2,5,6,7,10,13,19 ($60)


The horse broke well today,” Gaffalione said. “I had the horse inside, Dunph, going to the lead and then (Gun It) showed a little bit of speed. When I saw they were intent on going I just tried to get him back and got him to relax. He came back to me nicely and settled well down the backside. Got a little keen going into the far turn and wanted to move a little early. But I didn’t want to take too much away from him so I tried to sit as long as I could. He was waiting on horses down the lane but I kept him at task and there was plenty of horse there.”

“Mark (Casse, the trainer) and his team have done a great job,” Gaffalione said. “They’ve had a ton of confidence in this horse the whole way. It’s just an honor to be able to ride the horse. He’s just so professional, trains great and he’s a pleasure to be around.”

Tyler Gaffalione, Rode of War of Will to victory in the G2 Risen Star Stakes at the Fair Grounds
  • Ryan Dickey

    Ryan Dickey

      How many people have the courage and passion to quit their job of 17 years; pack up all of their belongings; and moved to another state to follow their dreams? Well, we want you to meet Ryan Dickey, “The Pressbox’s” newest addition, and latest friend. The man is on a ...

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