Sierra Leone

LOUISVILLE, Ky. (WDRB) -- I believe California Chrome (2014) was the last winner from my Barn of Baffling Kentucky Derby Selections. Or maybe it was Orb in 2013.

When your record is six for 45 picking Derby winners, why go through the joy of looking it up? Just accept the abuse.

I picked UConn and South Carolina to win the men's and women's college basketball national titles. I also picked the White Sox to be baseball's worst team. I try to stay in my lane.

But I'm here to serve, especially in a Derby as scintillating as Kentucky Derby 150.

Churchill Downs is absolutely sparkling with its $200 million renovation that features the new paddock. As Jerry Izenberg, the legendary New Jersey columnist deftly noted this week, Churchill has undergone more facelifts than Joan Rivers, holding its spot on the list of Ten Legendary American Sports Venues.

You've got D. Wayne Lukas, trying to win his fifth Derby and talking about chasing No. 6 next year when he will be 89 years old.

You've got a brilliant frontrunner in Fierceness and a powerful closer in Sierra Leone. I'd love to see them engage in the stretch and give us an Affirmed and Alydar battle to the wire.

The day's safest selection is this will be a Kentucky Derby to remember. Here's a Cheat Sheet to get you to the finish line late Saturday afternoon.

Best Horse

Let me make one thing perfectly clear: Fierceness is not my pick to win the Derby, although he certainly could. He's just my pick as the best horse.

He has the two best Beyer speed figures. He had a record performance in the Florida Derby. He has the pedigree. He has a Hall of Fame trainer (Todd Pletcher) and Hall of Fame jockey (John Velasquez).

If he runs his best race and nothing crazy happens around him, Fierceness should win the Derby.

Best Closer

Favorites often don't run their best race. Crazy things do happen around them.

If you're looking a colt to deliver a dazzling Derby moment, that would be Sierra Leone, a confirmed closer.

He went from ninth to first to win the Risen Star Stakes at Louisiana Downs. He went from ninth to first to win the Blue Grass Stakes at Keeneland, gaining more than 10 lengths on the leader in the final quarter-mile. That's moving when it matters.

But — (you knew there had to be a but, right?) — the post position draw did Sierra Leone, jockey Tyler Gaffalione and trainer Chad Brown no favors, placing him in the No. 2 hole.

The colt is likely to be shuffled to the rear of the field. Odds are Sierra Leone will be tasked with passing 15-19 horses in the final 3/8th of a mile.

He could do it. But he could also get blocked, bumped or discouraged. You have been warned.

Best Story

There are no bad stories when a horse wins the Kentucky Derby. Some are just more delightful than others.

I've narrowed my favorite Derby 2024 stories to two.

The first is Lukas and his persistent push to win his fifth Derby trophy (and first since 1999) at the age of 88. His colt, Just Steel, is No. 6 in the starting gate but No. 1 in the category of tugging at your heartstrings.

The second is the inspiring gentleman I wrote about Thursday: Larry Demeritte. Six years after he was told that he had six months to live, Demeritte is here with his first Derby horse: West Saratoga, an $11,000 yearling.

NBC Sports has been camped at Demeritte's barn all week. I expect his story will be prominent in the network's Derby coverage Saturday. As it should be.

Flip a coin between Lukas and Demeritte.

Best Local Story

Flip multiple coins this time. There three trainers representing local high schools.

Danny Gargan (Central High) will saddle Dornoch and Society Man. Whit Beckman (Honor Marie) represents St. Xavier High School. Brad Cox (Iroquois High) will attempt to win his second Derby with Just a Touch or Catching Freedom.

Best Jockey

Four of the 20 riders have won the race, but only two actually crossed the finish line first. Flavien Prat (Country House, 2019) and Florent Geroux (Mandaloun, 2021) moved up after a disqualification.

John Velasquez is clearly the pick, although the difficulty of winning the Derby is reflected in his record: 25 mounts, three wins and two seconds. As talented as Velasquez is, he's finished 10th or worse 14 times.

Best Jockey Yet to Win

That would be Irad Ortiz Jr. A top rider on the New York circuit, Ortiz has won two Belmonts and five Eclipse Awards. But he's 0/7 in the Derby, failing to finish better than fourth. Ortiz has the mount on Domestic Product.

Jockey Tidbit

Four riders will compete in their first Derby and six others have only ridden in the race once. That's a lot of inexperience.

Best Trainer

Lukas has won four times with 49 horses while Pletcher has won twice with 64. Cox (Mandaloun) and Mott (Country House) are the other trainers with Derby wins but they came on disqualifications.

Best Trainer Yet to Win

Give me Steve Asmussen, the Hall of Famer, who will saddle Track Phantom. He is 0/25 and Asmussen brought talented horses like Curlin, Gun Runner and Epicenter to the Derby.

Trainer Tidbit

Eight of the 17 trainers in the 20-horse field will make their Derby debut.

Best Wagering Strategy

I'm a fan of Neil Greenberg, who writes an informative wagering column on all sports for the Washington Post. (Story link, subscription required.)

On Thursday, Greenberg posted a story outlining his betting strategy for wagering on Derby 150. He strongly recommends exotic wagers: exactas, trifectas and superfectas.

Greenberg wrote that half of the winning exactas over the last decade paid an average of over $336.20 on a $2 wager. And the median payout on a 50-cent trifecta has been $848.45 since 2013.

Here are his 2024 Derby picks:

  • Exacta of No. 7 Honor Marie with No. 4 Catching Freedom
  • $1 trifecta with No. 7 Honor Marie and No. 4 Catching Freedom on top of either No. 7 or No. 4 in second, on top of No. 1 Dornoch, No. 2 Sierra Leone, No. 3 Mystik Dan and No. 8 Just a Touch for $8
  • 50-cent trifecta with 4/7 over 1, 2, 3, 8 over 4/7 for $4
  • 50-cent trifecta with 1, 2, 3, 8 over 4/7 over 4.7 for $4

My Derby Picks:

  1. Sierra Leone
  2. Just a Touch
  3. Fierceness
  4. Honor Marie

But I'd recommend Greenberg. I don't believe he is 6/45.

Happy Derby.

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