It’s Kentucky Derby Day and that means huge pools to take advantage of. And while there are some heavy favorites in the sequence (lookin’ at you NEWSPAPEROFRECORD, TIZ THE LAW and SERENGETI EMPRESS), I think I’ve built a strategy where we can maximize returns, even if two of those three horses lose.

Let’s get to it:

Race 11 (4:39PM ET) // G2 Longines Distaff Turf Mile S. // 1 Mile (Turf)

It’s amazing the difference a year makes. This time in 2019, I had written off #4 NEWSPAPEROFRECORD (4/5). She and I were done. Broken up. On the outs. But now we’re back again. Talk about an on-again/off-again relationship. As a 2YO she shined bright, winning 3-of-3 starts, including the Breeders’ Cup Juvenile Fillies Turf. As a 3YO she was 0-for-3 with losses at 1/5, 1/5 and 8/5. But she’s back in fine form, including two huge wins at Belmont (including a dominating score in the G1 Just a Game) and looks like a fair single in your Late Pick 4.

Race 12 (5:17PM ET) // G1 Derby City Distaff S. // 7 Furlongs (Dirt)

I really like this field. At one end of the spectrum, you have ’19 KY Oaks Winner SERENGETI EMPRESS (9/5) who will be gunned from the start. She’s going to benefit from the scratch of #7 LADY KATE (she ran Friday in the La Troienne) and if all goes according to plan, there may not be anyone to run with SERENGETI EMPRESS early. #1 MIA MISCHIEF (6/1) has speed but she generally prefers a stalking trip while #9 BELLAFINA (3/1) hasn’t shown a ton of early foot lately, but she does get a jockey change to Mike Smith. #10 CE CE (3/1) ran so well in the G1 Apple Blossom in April at Oaklawn but she has been a disappointment in two starts since. Perhaps that race took too much out of her?

Race 13 (5:50PM ET // G1 Old Forester Turf Classic S. // 1 1/8 Miles (Turf)

Chad Brown is the top turf trainer in the US and he sends out three horses in here - #3 ROCKEMPEROR (7/2), #4 DIGITAL AGE (6/1) and #8 SACRED LIFE (6/1). In my eyes, all three are ‘must use’ horses. I could regale you in their accolades, but they’re all trained by Brown for successful owners and all are more than capable of winning this race. I’ll also toss in #6 MR DUMAS (12/1). He loves racing at Churchill and switches to an inside post. His last race at Saratoga was good enough to win this. My colleague, Jeremy Plonk, has sold me on #2 BOWIES HERO (6/1). He seems to relish the more lush turf courses of Kentucky (as compared to the rock hard strips in California).

Race 14 (7:01PM ET) // G1 Kentucky Derby // 1 1/4 Miles (Dirt)

This is where we’re met with a question and I’ll play two separate approaches. On one hand, I’ll single #17 TIZ THE LAW (3/5). He’s a short price but he’s the best horse in the field (maybe the best dirt horse in the country?) and if he’s even close to as good as he was in the G1 Travers on August 8, he’ll win this for fun. Let’s play a ticket with a big(ger) base with him on top. And let’s also take advantage of the money on him – and these huge KY Derby Day pools – and throw in a ticket with some longshots. I’ll play a ticket with #7 MONEY MOVES (30/1), #13 ATTACHMENT RATE (50/1), #15 NY TRAFFIC (20/1) and #16 HONOR A. P. (5/1) on top for a smaller base. The good news? It’ll pay better than the primary ticket with TIZ THE LAW if we win.

My Tickets ($120 Total) 

Primary Ticket

Race 11: 4
Race 12: 1, 8, 10
Race 13: 2, 3, 4, 6, 8
Race 14: 17

Ticket Cost ($4 Base): $60.00

Backup Ticket

Race 11: 4
Race 12: 1, 8, 10
Race 13: 2, 3, 4, 6, 8
Race 14: 7, 13, 15, 16

Ticket Cost ($1 Base): $60.00