The way some people get excited about making their Oscar picks, I get excited for the Kentucky Derby. There’s a bit of history here.
In 1988, I was living in Atlantic City and working as the overnight radio voice of WFPG AM/FM. (That job is a story for another time.) Two college friends, Scott and Ed, called and asked if I wanted to go with them to the Preakness Stakes in Baltimore.
“That’s a horse race,” I said, “right?”
“Yep. And, oh, by the way, can you drive?”
Scott and Ed took a casino bus from NYC to the Jersey Shore, and met me early on a Saturday morning. I had worked the overnight shift, so had been awake since 1 p.m. the previous day. We got some food, hopped in my car, and made the two hour drive to Baltimore.
I had no experience with, or really knowledge of, horse racing, or even the Triple Crown races (Kentucky Derby, Preakness, Belmont Stakes). I didn’t know what to expect.
We paid thirty dollars to park on someone’s front lawn (it’s just how you do it on Preakness day), and made our way to the “infield.” The kindest description I can give the infield at either the Derby or Preakness is that of a drunken frat party. I’m not a party guy, and let me be clear, I’m not a frat guy. I was running on fumes, and the whole scene was kind of overwhelming. So I hunkered down, tried to tune out the beer swilling meatheads surrounding me, and focused on the racing. (If you haven’t been to the track, the featured race is one of twelve or thirteen contests that day, so you have hours to look at horses, pour over stats, and gamble.)
Scott & I at the KY Derby in 1995
Then, the worst possible thing that could have happened, happened. I picked the winner in the big race, a horse called Risen Star. I based my selection on the sole fact that Risen Star was a son of Secretariat, and hey, I’d heard of Secretariat. The thrill of cashing that ticket was like a hook in my mouth.
Scott, Ed, and I spent that summer going to the races in and around New York. I’ve since been to the Preakness a dozen times, the Derby four times (including my first trip on my 30th birthday — also a story for another time), and the Belmont Stakes nearly 20 times. I’ve been to tracks in California and Florida. Scott and I founded what was, at the time, the largest online horse race handicapping contest (the now defunct Public Handicapper). We went to Saratoga every summer. My first wife and I even played “I Got the Horse Right Here”(actually titled “Fugue for Tinhorns”) from Guys and Dolls while we cut our wedding cake. I was a horse player through and through.
Then, in 2008, 20 years after my first race, the best thing that could have happened, happened. I became a dad.
With demands on my time as a new father, and with a demanding day job, something had to give, so I retired my handicapping pen and said goodbye to active involvement in horse racing. Scott took sole control of Public Handicapper — which he has since parlayed into an awesome new site, Sport of Kings — and, stick a fork in me, I was done. Except, of course, for once a year.
Derby Week is still a big deal with me. I get the PPs (Past Performances) from the Daily Racing Form and dive deep on the race. I analyze the pace, class, speed, and breeding of every horse running. I look at every trainer and jockey, and their records on the track, at the distance, in stakes races. Kristen and I hold the best Derby part west of the Mississippi — last year, due to COVID, we slapped numbers on the backs of all the neighborhood kids and made them run around our cul de sac (they loved it) — and I make real world bets, very few of which ever pan out. But still… This is my week. (Side note to our many friends who have attended past Derby parties. For COVID safety reasons, we’re limiting this year’s party to neighbors only. Expect an invite next year, which, I promise, will be a blow out!)
So, on the foundation of that backstory, and with unbridled enthusiasm, I present to you my horse by horse analysis, in Post Position order (with #1 being closest to the rail and #20 being furthest from the rail) of this year’s Run for the Roses.
Known Agenda — No horse has won from the inside post since Ferdinand in 1986. The horse on the rail either has to burn a lot of early speed (in what is a very long race for three year old horses) or gets shuffled too far back. While it is technically the winningest post position since 1900, it has not fared well lately. Known Agenda did win the Fla Derby in his final prep for the KY Derby, but I didn’t like the way her bore out to the middle of the track in doing so. I think he regresses off that effort. I’m ignoring this horse completely.
Like the King — This post is even worse. No horse has won from post #2 since Affirmed began his Triple Crown winning campaign in 1978. Plus, this horse has been running against weaker competition. Instatoss.
Brooklyn Strong — This horse is 50-1 on the morning line, and at those odds, he’s intriguing. BUT, he’s also been running against weaker competition, his trainer is largely untested, his breeding is suspect, and it’s just too much of a stretch. Pass.
Keepmeinmind — This horse is my long shot bomb. He’ll be a very high price (morning line odds are 50-1), and offers real value. He was a STELLAR two year old, running in and finishing very well in the biggest stakes races in the country. While his three year old campaign has been lackluster, I’m finding enough reasons to forgive his two races in 2021 that I think he’s a very playable horse. Plus, the trainer is taking blinkers off for this race (an angle this train wins with fairly often), and he (the horse, not the trainer) had a monster workout last week. I’ll use him in all of my bets.
Sainthood — Too lightly raced and too untested against a field this strong. No thanks.
O Besos — Sounds like Oh Bezos. As in Jeff Bezos. Until recently I owned an independent bookstore. That alone disqualifies him (the horse and Jeff Bezos) in my mind. Plus, his best finish against good horses was a weak third. He’ll have to make a big step forward to win today, and I don’t see it.
Mandoloun — He finished up the track in the Louisiana Derby. Even if I make an excuse for that race — and I can’t find one — the rest of his line is simply unimpressive. His breeding is impeccable, which does scare me a bit, so he might be live long shot, but I’ll still play against.
Medina Spirit — Never worse than second running in all of the biggest races for two and three year olds on the West Coast. His trainer/jockey combo — Bob Baffert and JR Velazquez — is one of, if not the, winningest trainer/jockey combo in Derby history. He looks to improve off his last race, and is an incredibly live play at his ML odds of 15-1. I’ll use in all my bets.
Hot Rod Charlie — I should like this horse on the name alone (my son is Charlie), but there’s more to like here than just the name. His last race, a win in the Lousiana Derby, was a tour de force. He looked great in that race, and looks likely to improve. He finished second to today’s favorite in the biggest race last fall, losing by less than a length. Charlie is peaking at the right time. His morning line is 8-1, which is tasty, but he’s getting bet heavily on Sport of Kings, so don’t expect that price at post time. Either way, a must use.
Midnight Bourbon — His breeding says he’ll like the KY Derby distance (1 1/4 miles), and he’s an accomplished runner. It will all come down to the pace for this guy. If the first half mile is fast (:47 or so), I think MB fades in the stretch. If it’s slow, look out. I plan to use him underneath in my superfecta.
Dynamic One — Slower, coming out of a suspect race, untested against good horses. Pass, pass, and pass again.
Helium — See above. No thanks.
Hidden Stash — While this horse seems to like Churchill Downs, he’s run poorly when facing good competition. I have to take a stand against.
Essential Quality — A deserving morning line favorite, Essential Quality is undefeated in five career starts. He’s gotten faster and more impressive with each successive race. The only thing I don’t like is the 2-1 ML price. I have to believe this horse will be there at the end, but will likely not offer enough value to use in 1st or 2nd place in my exotic bets (trifectas and superfectas, see below), so I’ll use him underneath.
Rock Your World — Also undefeated, but has only raced three times. He looks like he’ll want the lead, and breaking from all the way out in the 15th post position, he’ll have to spend a lot of energy early to run at the front of the pack, and/or he’ll run wide all the way around the track, which will make him tired at the end. I see this horse, who could be second or third choice in the betting, fading in that long Churchill stretch. I’ll take a stand against.
King Fury — He had a nice win in his last race out, but it was a come from behind win against a very hot pace. (This means the horses in the lead ran too fast too early and lost steam. King Fury was there to pick up the pieces.) When faced with better, he hasn’t performed. Pass.
Highly Motivated — He has the same sire as super horse Authentic, so you know he can get the distance, and you know he can win. He was only a neck behind the favorite in their last race, yet this horse is 8-1. I don’t like the post, but I love the value. I’ll play him in many of my bets.
Super Stock — This horse won the Arkansas Derby. I have been burned by more AK Derby winners than I care to remember, so I’m playing against on principle. Plus, with his running style, the outside post is just no good.
Soup and Sandwich — I was completely ignoring this horse until I talked to the aforementioned Scott. Still a very active horseplayer, Scott loves Soup and Sandwich, so I gave the horse a much harder and much longer look. Aaaaaannnnndddddd… I still think he runs up the track. He never raced as a two year old, has run in only one graded stakes race, and will get slaughtered in breaking from post #19. Scott and I haver a side bet as to which of our long shot bombs — Soup and Sandwich for Scott and Keepmeinmind for me — finishes better. The loser has to do a Wayne’s World style “I’m not worthy” video for the winner.
Bourbonic — Monster move from last to first to win the Wood Memorial in his final prep for the Derby, but that was a lackluster field. Even though the post doesn’t really hurt his running style, he’ll have to pass 19 horses here, compared to 8 in the Wood. Too tall an order.
My Picks:
1. Medina Spirit
2. Keepmeinmind
3. Hot Rod Charlie
4. Essential Value
5. Highly Motivated
6. Midnight Bourbon
My Bets:
$2 Win/Place/Show ($6)
Medina Spirit
(I win if the horse finishes first, second or third)
$2 Win/Place/Show ($6)
Keepmeinmind
$2 Win/Place/Show ($6)
Hot Rod Charlie
$1 Exacta Box ($30)
Medina Spirit/Keepmeinmind/Hot Rod Charlie/Essential Value/Highly Motivated/Midnight Bourbon
(I win if any combination of these six horses finish first and second)
$1 Trifecta ($16)
1st – Medina Spirit/Keepmeinmind
2nd – Medina Spirit/Keepmeinmind/Hot Rod Charlie
3rd – Medina Spirit/Keepmeinmind/Hot Rod Charlie/ Essential Value/Highly Motivated/Midnight Bourbon
(I win if I pick the horses in order to finish first, second, and third)
$1 Superfecta ($36)
1st – Medina Spirit/Keepmeinmind
2nd – Medina Spirit/Keepmeinmind/Hot Rod Charlie
3rd – Medina Spirit/Keepmeinmind/Hot Rod Charlie/ Essential Value/Highly Motivated
4th – Medina Spirit/Keepmeinmind/Hot Rod Charlie/ Essential Value/Highly Motivated/Midnight Bourbon
(I win if I pick the horses in order to finish first, second, third, and fourth)
Total Bets: ($100)
Now, if you’re smart, you’ll look at the horses I picked, and choose any one of the others.
Good luck, and May the Horse Be With You!
