Handicapping the Kentucky Derby

2008 represents the fourth year in a row that I have attempted to successfully handicap the Kentucky Derby. My friend J got me into horse racing during senior year of college, and although I haven’t had as much time to spend on it as would have liked in the past years, I still manage to spend a bit of time each year handicapping the big races. I usually end up spending at least one day a year out at a race track (either Arlington when in Chicago or Hoosier Park during my brief stay in Indianapolis) and watch the Big Four races (the Triple Crown races – Kentucky Derby, Preakness Stakes, and Belmont Stakes; and the Breeders’ Cup races in September). J takes these races much more seriously than I do, which may explain why he has managed to successfully handicap 3 of the last 4 Derbies.

In all likelihood, 5:30 p.m. tomorrow will come and go with this also being the fourth year of my failing to correctly handicap the race. The Derby is one of the most difficult horse races to predict: with 20 horses of such high caliber, the horse that stands in the winner’s circle often gets there through luck more than anything else. Terrible pole positions, bad trips, unpredictable paces and simply being in the wrong place at the wrong time have doomed countless contenders over the years.

With that said, it would be tempting to do as I have done in recent years with the NCAA Tournament – write it off as being impossible for me to predict. Unfortunately, I have no real sense of pattern recognition, so I’m going to take another crack at the Derby this year. I’m buoyed by my correct predictions in the 2006 Belmont Stakes and 2007 Preakness, so maybe I have at least some idea what I’m doing.

Contenders

The big boy this year is Big Brown. He’s coming off a blazing wire-to-wire victory in the Florida Derby with a 106 Beyer. Unfortunately, he’s also drawn the 20th post – furthest out from the field. His only shot is to try the same thing he did in that race – jump out to a lead and try to take the field all the way around. Coming at from the far post, though, will be much more difficult this time, especially with speedsters like Bob Black Jack in the field. My guess is that Big Brown gets caught in traffic and does no better than third.

I’m a big fan of closing-style horses (hence my pick of Jazil in the 2006 Belmont Stakes), so I like some combination of Pyro, Colonel John, and Denis of Cork. Both Pyro and Colonel John are going to have lower prices, so I’m keying most of my bets this year to Denis of Cork (expected to go off somewhere between 15-1 and 20-1). He’s coming from the 16 position – the first after the break – which should let him slide into a comfortable position between 5th and 10th in the pack early on, allowing him to shoot close to the rail and make a big surge at the end. Pyro and Colonel John could have similar trips.

I’m also keying in Gayego, Z Fortune, Court Vision and Bob Black Jack into my exotics. Each one is either a speedster or closer who could easily contend for place or show.

My Picks

Ultimately, I decided to go with a $10 win bet on Denis of Cork, a $2 show bet on Big Truck (a Barclay Tagg horse with the worst odds in the field, juuuuuuuuuust in case Giacomo’s ghost* decides to return), $5 exacta boxes on Denis of Cork with Big Brown and Pyro with Colonel John, and various trifectas and superfectas with each of the horses named above leading to $50 in bets. I’ve structured each bet in such a way that if any of them hit, I will at least cover my overall bets – a lesson I learned the hard way when I keyed a bunch of Barbaro-based exactas for the 2006 Preakness, none of which would have covered my overall cost even if Barbaro hadn’t gotten hurt.

I’ll post the results on Sunday.

*Stop composing angry comments – I know Giacomo’s still alive.