Ed DeRosa's expert betting picks for all 14 Kentucky Derby Day races at Churchill Downs

Are you ready for Kentucky Derby day? Whether you’re in it for the horses, the gambling, the fashion, the juleps or some combination of all or some of the above, as someone who gravitates toward the horses and gambling part of it, I can promise you it is the best day of the year to play the races.

From top to bottom, it is one of the best race cards all year anywhere, and of course the Kentucky Derby (Race 12 of 14) itself is a compelling, challenging puzzle that rewards its solvers like no gambling enterprise in the world.

So, let’s make some money!

Race 1 picks: 3-1-7

I expect some opportunity right off the rip, as No. 1 Extra Anejo is sure to take a lot of money on his return following a brilliant career debut. But that’s a long layoff, and the Ragozin Sheets say No. 3 Federal Judge was faster when he won his career debut on April 1 at Oaklawn Park. I would be shocked if anyone else won besides one of my top two picks.

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Race 2 picks: 8-3-6

I would love to see No. 8 Quality Chic (3-to-1) go off at a longer price than No. 1 Cape Trafalgar (2-to-1) — as the morning-line suggests — but I don’t see how Quality Chic is not the favorite. The biggest concern is pace, as the rail has it in spades and might be tough to catch, but “on paper” the ocho is faster. Of course, they don’t run these on paper.

Race 3 picks: 14-1-2

There is a lot of early speed in this race, so that definitely compromises the chances of No. 14 Petulante, but at 6-to-1 I’ll gamble that he can carry his speed from the outside post and trainer Victor Barboza Jr. is just not going to take big money in this field. No. 1 Bright Future will get a ground-saving trip from the rail and will just need room behind any fading speed.

Race 4 (Derby City Distaff) picks: 3-5-2

Champion Breeders’ Cup Filly & Mare Sprint winner Goodnight Olive has every right to be the favorite here riding a seven-race win streak. But No. 3 Wicked Halo is a faster, stronger 4-year-old than we saw last year when she had some buzz to her before she finished third behind Goodnight Olive in the aforementioned Breeders’ Cup female sprint. She is absolutely in the mix at two- to three-times the price as Goodnight Olive.

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Race 5 (Churchill Distaff Turf Mile Stakes) picks: 4-7-2

Another favorite we’re going to try to beat. I’m not sure there’s any big prices in this early Pick 5 (Races 1-5), but a string of $8 winners beating a bunch of favorites can still pay very well, especially on Derby day. So it goes in this race with 7-to-5 Spendarella looking vulnerable in her 4-year-old debut off a long layoff. No. 4 Wakanaka was 2-to-1 in the Pegasus World Cup Filly & Mare Turf, and the races that day at Gulfstream Park have come back well. Hall-of-fame trainer Bill Mott has had several big stakes wins with his fillies and mares the past two weeks. Both of Chad Brown’s fillies fit, but I favor Mott “on top” expecting that one to be the biggest price.

Race 6 (Knicks Go Overnight) picks: 2-6-3

Kentucky Derby day will be May 4 next year, which would make No. 3 Baby Yoda the biggest hunch play of the day, but alas, this is May 6, and we’re going to try to beat this favorite. As a Cleveland native, No. 2 Masqueparade tugs at my heart strings as an Ohio Derby winner. This is a big ask off the layoff but 6-to-1 compensates us. No. 6 Zozos cuts back to a one-turn mile, which intrigues me given the win last out but won on debut going six furlongs.

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Race 7 picks (Turf Sprint Stakes) : 7-11-10

Going with the early speed here in No. 7 Nothing Better, as he is the speed of the speed while also sporting the Frank Angst jockey angle with Manny Franco back aboard after winning last time. No. 11 Motorious might be a better horse overall but will have a lot to do late to mow down our top pick.

Race 8 picks (Pat Day Mile): 1-3-7

At 8-to-1, No. 1 Kangaroo Court is our best bet of the day. Pride before the fall and all that, but it’s just not supposed to be this easy to find most likely winners at this type of price. Biggest question mark is the one-turn mile being by the Discreet Cat stallion Dads Caps, but the numbers say he’s quickest and they’ll have to catch him inside the eighth pole. Best bet.

Race 9 (American Turf Stakes) picks: 5-4-1

No. 1 Major Dude was pointed to the Kentucky Derby after his runner-up finish in the Jeff Ruby Steaks, but he did not qualify via points so trainer Todd Pletcher rerouted to this spot. Those horses usually take too much money, which is why I looked elsewhere and landed on No. 5 Johannes, who is undefeated in three starts on turf. No. 4 Talk of the Nation figures to get a good pocket trip under new rider Tyler Gaffalione.

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Race 10 (Churchill Downs Stakes) picks: 7-6-10

One of three Breeders’ Cup winners on the card, No. 7 Cody’s Wish makes his 5-year-old debut where he is undefeated in four starts. All those came at a mile, but the biggest win of his career until the Breeders’ Cup came going seven furlongs when he upset Jackie’s Warrior in the Forego. No. 6 Tejano Twist would benefit if the race sets up for closers and our top pick doesn’t fire.

Race 11 (Turf Classic Stakes) picks: 7-5-10

I thought No. 7 Hong Kong Harry was a cinch in the Kilroe Mile last out, and that was a terrible opinion as he finished a dull fourth at even money. Now we get back out to nine furlongs where he has won two of three races. Trainer Phil d’Amato has done well in Kentucky this year, and the price shouldn’t drop too bad off the loss and presence of last year’s winner, Santin.

Race 12 (Kentucky Derby) picks: 5-9-11

The Kentucky Derby presents unique challenges to the horses who compete, the trainers involved in preparing them to do so, and the jockeys who have to execute the plan. No. 5 Tapit Trice checks every box of a horse I’m excited to play: He has not missed any of his targets on his prep schedule, Pletcher seems to have him at maximum fitness for this race, and jockey Luis Saez rode him perfectly from the rail in the Blue Grass after seemingly being left with too much to do in the Tampa Bay Derby. What we have seen so far from Tapit Trice would be good enough to win, but I think he can move forward, and that makes him super dangerous. No. 9 Skinner has been win shy but has flashed moments of brilliance that can get the job done. No. 11 Disarm is more an exotics sweetener for me, but we’re coming off a $162 winner, so we have to throw in a bomb.

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Race 13 picks: 2-9-8

No. 2 Equivoque was awesome on debut, and he has since worked Pletcher’s Kentucky Derby entrants. There are clearly high hopes for this colt, and he easily stands tallest among this group as one of the most likely winners on the day.

Race 14 picks: 2-9-14

I love that we’re closing this card with a strong opinion on the hard four (2-2) because that will let us spread a bit in the Old Forrester Turf Classic and Kentucky Derby on certain tickets. No. 2 Everso Mischievous was 3-to-5 on debut and just missed to a next-out winner. If someone runs with him early and slows him down late No. 9 Mullikin could roll late with Flavien Prat hopping aboard.

This article originally appeared on Louisville Courier Journal: Kentucky Derby 2023: Betting picks for all 14 races at Churchill Downs