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Picking and Choosing in Incredible Kentucky Derby Day Pick 5

by Jerry Shottenkirk

May 5, 2018

Perhaps the most important question on Kentucky Derby Day is “How much do am I willing to spend?”

With the buffet of greatness that is known as the Kentucky Derby Day card, you can go very deep into each race, so it’s basically a day in which to take a stand – make a decision.

If you can’t whittle down the Pick 4 or Pick 5 races (the latter targeted here), you’ll easily get into the thousands. If you can only cut your Derby selections to six or seven horses, you are looking at an enormous ticket, unless, of course, you can take several singles in races leading up to the headliner. With the quality of each of these races, you probably don’t want to do that.

So instead going the several hundred to several thousand route, I’ve settled on a $54 ticket.

Here’s a look at the Pick 5 races:

Race 8 (2:45PM ET) - Churchill Downs Stakes (Gr 2, $500,000)

When Whitmore brings his ‘A’ game – which is quite often – he’s usually the one to beat. If you need proof (other than the past performances) of Whitmore’s quality, watch a replay of the G3 Count Fleet Sprint Handicap at Oaklawn (Race 9, April 14). The turn of foot he displayed in the final three-sixteenths was as impressive and you’ll see, and he moved his record of 10 of 18.

Imperial Hint is the favorite in the race and joins Whitmore on the Pick 5 card. His string of five wins, which ended with a runner-up to the outstanding Roy H in the Breeders’ Cup Sprint, gave him the distinction of being elite.

Race 9 (3:37PM ET) - American Turf Stakes (Gr 2, $300,000)

Three in this field are represented on the suggested ticket: Threeandfourpence, River Boyne and Captivating Moon.

West Coast-invader River Boyne may have the edge. The Irish-bred is 3 of 4 in America after starting his career in his native land. He hasn’t been in a graded stakes race but was a steady and consistent closer as he won three straight at Santa Anita, including the Pasadena Stakes on March 17.

Threeandfourpence tried Mendelssohn in his last two. He was 2nd to the Derby entrant at Dundalk (Ire), then didn’t fire at all in the UAE Derby. He broke his maiden on turf at Fairyhouse (Ire).

Captivating Moon has done very well on turf, which two wins and two 2nds in four trips. He closed for 2nd in the Transylvania Stakes over a yielding course at Keeneland last out and a similar run would make him a big player today.

Race 10 (4:28PM ET) - Pat Day Mile Stakes (Gr 3, $300,000)

There’s a trio worthy of attention here, including National Flag, Madison’s Luna and Mask.

National Flag was a promising 2-year-old last fall and has marked himself as a capable sprinter as a 3-year-old. He was an impressive optional claiming winner at Gulfstream but really put himself on a different level when he won the Bay Shore at Aqueduct.

Madison’s Luna and Mask – a pair of Tapit colts – will put undefeated records on the line. Madison’s Luna was a sharp maiden winner at Tampa and then ran off an easy and impressive score in the Hutcheson Stakes at Gulfstream. He likely won’t have a problem with the mile.

Mask has won his two races by daylight, including the Mucho Macho Man at Gulfstream. He steps up in company today but unquestionably has a great deal of ability.

Race 11 (5:25PM ET) - Old Forester Turf Classic Stakes (Gr 1, $500,000)

Deauville and Beach Patrol are clearly capable runners and will be strong factors here.

Deauville has just two starts in North America (3rd in Arlington Million) and (11th in Woodbine Mile) and ran a decent 2nd at Newmarket (GB) in his only start this year. Deauville put a head in front turning for home in the Arlington Million and finished less than a length behind Beach Patrol.

Beach Patrol doesn’t win every time, but he’s always a contender and has hit the board in 14 of 17, including five wins. His back-to-back wins in the Arlington Million and the Turf Classic (at Belmont) put him at the top of his division here and he ended the year with a half-length loss to Talismanic in the Breeders’ Cup Turf.

Race 12 (6:50PM ET) - Kentucky Derby (Gr 1, $2,000,000)

I’m sold on Justify, but this is the Derby, and singling the Derby is showing at a lot confidence. So many things can happen, and while Justify as the edge, it’s a 20-horse field and actually anything can happen.

His West Coast rival Bolt d’Oro has been an honest and capable performer and doesn’t run any bad ones. It wasn’t his day when he was 3rd as the 7-to-10 favorite in the BC Juvenile but he has come back with promising performances this year. He lost the San Felipe by a head to McKinzie but was awarded the win for interference and then was 2nd to Justify in the Santa Anita Derby. He certainly belongs with the Justify, when means he belongs in this one. He also gets Victor Espinoza, who has established himself as the one of the best big-money riders in the sport.

The remaining one of the ticket is Audible, who clearly among the best as he’s won four straight. He whistled in the Holy Bull and was nearly as impressive in the Florida Derby.

Here’s the suggested ticket for the Pick 5 ending with the Kentucky Derby:

8) #1 Whitmore, #3 Imperial Hint
9) #3 Threeandfourpence, #6 River Boyne, #9 Captivating Moon
10) #1 National Flag, #7 Madison’s Luna, #8 Mask
11) #1 Deauville, #10 Beach Patrol
12) #7 Justify, #11 Bolt d’Oro, #5 Audible

50-cent Pick 5: 1-3 with 3-6-9 with 1-7-8 with 1-10 with 7-11-5 ($54)