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Live Longshot Caps Kentucky Derby Day Pick 5

The quality on the Kentucky Derby Day card at Churchill Downs on Saturday is deeper than a West Virginia coal mine, making for a difficult Pick 5 puzzle to piece together. Five stakes races, culminating with the 150th Kentucky Derby, comprise the sequence. It paid more than $17,000 for a 50-cent bet in 2023, and better than $247,000 when Rich Strike won the 2022 Derby at 80-1 in the Horse Racing odds! It returned “only” $2,974.85 in 2021.

Here’s a modest $16 ticket that can potentially pay well, at least if one of our longshots – especially in the Derby – comes home. That won’t be a horse trained by Charles Appleby, whose charges could be favored in two of the races. We’ll hold our breath early with a single in the first leg, two horses apiece in three others and four in another.

Live Longshot Caps Kentucky Derby Day Pick 5
Horses return to the winner's circle - Michael Reaves/Getty Images/AFP


  • The rain was expected to stop Friday night, so it could be fast by post time for the Kentucky Derby, which is 6:57 p.m. ET. There is a one-in-three chance that showers return at 5 p.m. ET on Saturday, though. The turf course is not expected to be firm. It was yielding on Friday, so it could be upgraded to good on Saturday.
  • NBC provides Kentucky Derby Day coverage from 2:30 p.m. to 7:30 p.m. ET.


Race 8: Grade 2 Pat Day Mile

1 mile. Post time: 2:46 p.m. ET

Conor (post 8), the 5-2 morning-line favorite, makes his third career start after matching 86 Beyer speed figures. Conor isn’t as fast early as others in here, which should work in jockey Jose Ortiz’s favor. Conor set the pace for much of the Blue Grass Stakes before losing the 1⅛-mile race by eight lengths. It’s unlikely he’ll be on the lead here, so look for him to sit behind the confirmed speedballs and go by in the stretch. Chad Brown trains the $1 million son of Twirling Candy, who broke his maiden in a one-turn mile at Gulfstream.


Race 9: Grade 2 American Turf Stakes

1 1/16 miles (turf). Post time: 3:40 p.m. ET

When trainer Charles Appleby ships a horse across the Atlantic Ocean, it wins at a high rate. Appleby sends out Legend of Time (5), the 7-2 favorite in his U.S. debut. Frankie Dettori rides as William Buck stays in England to ride an Appleby horse in the 2000 Guineas Stakes at Newmarket. Legend of Time, 4-for-5 lifetime after an easy score in Dubai, should receive an excellent trip behind the speed and pounce in the stretch.

In case Legend of Time doesn’t fire, Lord Bullingdon (8) could be the longshot to make your ticket at the BetUS racebook. Lord Bullington is one of five horses entered who last raced in the Grade 3 Transylvania Stakes at Keeneland. Lord Bullington finished fourth over the good going by 1¼ lengths, pairing up career-high 82 Beyers. The Lord should be tighter while making his third start of the form cycle for trainer Michael McCarthy and jockey John Velazquez.


Race 10: Grade 1 Churchill Downs Stakes

7 furlongs. Post time: 4:31 p.m. ET

We’ll go four-deep in another wide-open affair with the top four choices on the morning line with Mr. Wireless (4) the longest price at 6-1. Mr. Wireless came back running as a 6-year-old with a 102 Beyer, and could sit the trip behind the speed. Zozos (6) likes to be on the front end, but he may not make the lead. He will be forwardly placed, though, giving him an excellent chance.

Hoist Gold (11) threw in a clunker in the Saudi Cup at 1⅛ miles and comes back sprinting. His bullet workout two-back could be an indication that his race in the Middle East was an aberration. Hoist Gold won the Cigar Mile in the slop at Aqueduct in November, so an off track would be welcome. Tejano Twist (2) will need a fast pace to set up his closing kick. Picking up Irad Ortiz Jr., the world’s best jockey, enhances his chances for trainer Chris Hartman.


Race 11: Grade 1 Old Forester Bourbon Turf Classic

1⅛ miles (turf). Post time: 5:27 p.m. ET

Naval Power (11), trained by Appleby, drew the outside post but the versatile sort should give Dettori options. Naval Power earned an eye-popping 104 Beyer in finishing second behind Master of the Seas, the 2023 Breeders’ Cup Mile champion. Naval Power’s biggest threat appears to be I’m Very Busy (6), ridden by Irad Ortiz Jr. and trained by Brown. I’m Very Busy comes off a 3¾-length victory over good going in a Grade 2 at the Fair Grounds, earning a 103 Beyer. Never Surprised (8) is likely to set a brisk pace, setting it up best for midpack types.


Race 12: Grade 1 Kentucky Derby

1¼ miles. Post time: 6:57 p.m. ET

Fierceness (17) looms large as the early 5-2 favorite who packs a 110 Beyer speed figure. His 13½-length victory in the Florida Derby shows what he’s capable of on his best day. Fierceness, though, has demonstrated a good race, bad race pattern, so he cannot be completely trusted. He seems destined for a good trip, though.


Honor Marie (7) will have to pass about 15 horses to win, but he’s capable of doing so. The post is excellent and he should have a fast pace to work with – two key factors if he is to reach the winner’s circle. Also, the potential for an off track shouldn’t matter much to the 20-1 morning-line shot, who will be less than that at post time.

Honor Marie makes his third start of the year – an ideal time for it – and is working up a storm for trainer Whit Beckman, a Louisville native with his first Derby horse. Honor Marie was born on May 4, 2021. Is there a better way to celebrate your third birthday?


THE HORSE RACING BET: 8 with 5,8 with 2,4,6,11 with 6,11 with 7,17



Questions of the Day

Who is favored to win the 150th Kentucky Derby?

Fierceness (post 17), with John Velazquez riding, is the 5-2 morning-line favorite to win the 150th Kentucky Derby.

What does the Pick 5 usually pay?

That depends on the odds of the winners in each race. The Pick 5 could pay less than $100 if all five favorites win, or several thousand if longshots are in the mix.

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