Early Clever Kentucky Derby Trifecta

triple crown

Don’t ask me how many days we have until the Kentucky Derby. I know it’s less than 90. Suffice it to say, a lot is going to happen between now and then. A lot! However, simple things like time and patience should not stop us from rampantly and irresponsibly speculating as to the make-up of the Derby field. And from there, taking an early stab at bet formation is just one reckless step away. Let’s get to it!

For starters, I feel compelled to tell you that picking Kentucky Derby winners has been a difficult thing for me since my first Derby bet in 1995 (Suave Prospect). Since then, I have had win bets on only two Kentucky Derby winners- Fusaichi Pegasus (2000) and Animal Kingdom (2011). That said, I am way, way up on the Derby from an earnings perspective. In 2001, I had a future wager on Monarchos. In 2005, in addition to my future wager on Giacomo, I backed in to the Derby exacta to the tune of $4,900 or so thanks to my decision to play a $1 exacta box on every horse in the race on whom I had an active future wager. Thanks to Closing Argument for running 2nd that day. In 2006, top long shot Bluegrass Cat managed 2nd behind obvious-inclucde Barbaro, and I took home over $5,000 thanks to the exacta. And in 2019, the “win” by my top long shot, Country House, gave me the Derby trifecta for a little over $11,000. Win/place bets on Pioneerof The Nile, Lion Heart and Good Magic have added to the winning days, as all three ran 2nd.

All in all, since 1995, I’d say I am up close to $25,000 on the Kentucky Derby. Not bad for a race where I’ve struggled to pick winners. And for my next trick, I am going to attempt to hit the Derby trifecta right here, right now. In mid-February. And to make it even more amazing, I am going to do it by using three horses that, as of last week at least, were pretty much on no one’s radar.

1st: Three Technique

This horse is legit. His 3yo debut in the Smarty Jones was pretty impressive if you ask me or anyone else for that matter. The winner got away with slow fractions on a speed-favoring track, and Three Technique just could not catch him. I’m a documented sucker for any horse that can win by open lengths going 7F and then take a step up on the Beyer scale in the route debut. As of this writing, he appears to be about 3-4 days late for a workout, so I’m slightly concerned that my current Derby pick (subject to change at least 37 times between now and Derby Day) might be experiencing a physical issue. Plus, Jeremiah Englehart isn’t exactly known for his Triple Crown prowess. But, if all is OK, this guy is my early pick to win based on current value. (Yes, of course others are more likely to win at this point. I’m trying to get clever here, and I think Three Technique is super-interesting.)

2nd: Chestertown

Golden Soul. Commanding Curve. Country House. Go back and watch the replays of their respective Derby preps. Dig up their PPs. They all came into the Kentucky Derby at long odds, with lowish Beyers, and with sort of the same running style. They never dazzled anyone. They were usually passing horses late in their preps as they lost ground to the winners in the stretch. And all three of them crossed the wire second in the Derby. I would also add Keen Ice to that list, but he experienced trouble in the Derby and didn’t hit the board. You could also maybe add Lookin’ At Lee to that list, but he was more of a stone cold closer, and that’s not the running style I’m talking about. Anyway, I believe Chestertown, if he takes a modest step up in his next start and earns some Derby points, is going to be a very interesting long shot in the Kentucky Derby. He should have won on Saturday, but just wasn’t able to get into the clear and close into the slow pace. He’ll get the Derby distance. Will he get it quickly enough to complete the exacta? Eh, I’m not so sure he won’t. Again, I get it. Others have done way more so far. But keep an eye on this guy in his next start. He reminds me so much of other Derby bombs who ran huge races when no one expected it. And look at that $2,000,000 price tag!

3rd: Wells Bayou

I used Wells Bayou in a Southwest exacta box but neglected to include the winner. Ultimately a very dumb move since I have been a fan of Silver Prospector all along. Nevertheless, Wells Bayou is a serious racehorse and he proved it in the Southwest. He didn’t exactly fly home, but after running an opening 1/4 in under :23, can you blame him? It would not surprise me in the least if this guy ends up being my Derby pick. But for now, it’s a little easier for me to see him setting the Derby pace and getting run down late when that final 1/8th starts to feel like it’s being run uphill. That’s why I’ve got him 3rd at the moment.


  1. Susie Hebery on February 23, 2020 at 11:26 pm

    You do have A LOT going on before Derby-Day! Love you!

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