18 Picks and Counting: My struggle to pick a Kentucky Derby winner

Profile Picture: Vance Hanson

April 20th, 2015

It’s not exactly a Chicago Cubs-type record of futility, but it’s certainly not a record I’m proud of.

Not since Grindstone got his nostril in front of Cavonnier in 1996 have I cashed a win bet in the Kentucky Derby (and even then my payoff was depressed by the fact Grindstone was coupled with the more highly-regarded Editor’s Note).

That’s 18 consecutive losing Derby selections.

What can I attribute this ice-cold streak to? Reviewing my top picks, it’s easy to lump them into categories that go a long ways toward explaining why I’m not necessarily the guy to ask for a winner in this particular race.


It seem preposterous that horses like Point Given (2001) and Afleet Alex (2005), who towered over their peers in the Preakness and Belmont, failed to get the job done at Churchill Downs, but they did. Lookin at Lucky (2010) also went on to be named champion three-year-old, but had the misfortune of drawing post 1 in the Derby and paid for it with a terribly rough run passing the stands in the first quarter-mile. I suppose I should have found another horse to pick after the post-position draw, but stubbornness in the belief he was still the best horse prevailed.


My formative years in racing were the late 1980s, halfway through a two-decade drought for post-time favorites in the Kentucky Derby. Consequently, I’ve been a little slow to embrace the chalk even though they’ve won six of the past 15 runnings.

Not expecting Fusaichi Pegasus to be the horse to snap a 21-year losing streak of favorites, I sided with The Deputy (2000), whom Fu Peg had only beaten by three-quarters of a length in the San Felipe. Considering The Deputy lost the Derby by more than 23 lengths and never ran again, I don’t think I got a legitimate run for my money.

With his pedigree, I was not convinced Smarty Jones would be effective at 1 1/4 miles. I wound up picking the horse that turned out to be a slower racehorse but a better stallion: Tapit (2004).

Street Sense, Orb, and California Chrome were all favorites I greatly respected, but I simply felt duty bound to oppose them, respectively, with the longer-priced Any Given Saturday (2007), Revolutionary (2013), and Wicked Strong (2014).


Having cashed on a Louisiana Derby winner the previous year, it was hard for me not to love the deep-closing Crypto Star (1997), who won the Louisiana Derby and Arkansas Derby en route to Churchill Downs. Alas, he was a cut below in of the deepest crops of three-year-olds I’ve ever seen.

Ten Most Wanted (2003) won the Illinois Derby, Travers, and Super Derby, and was a close second in the Belmont and Swaps, but chose to run one of his worst races of the season in the Run for the Roses.

Lawyer Ron (2006), another Arkansas Derby winner I fancied, was no match for the brilliant but ill-fated Barbaro, but he did go on to be named champion older male the following year.


Owner Ahmed Zayat has the likely favorite this year in American Pharoah. By sheer coincidence, I’ve also felt his pain over the years by backing three of his previous starters. Nehro (2011) and Bodemeister (2012) both performed solidly to finish second, but Z Fortune (2008) was one of my more obtuse stabs as I tried to find anything that could beat Big Brown, who broke a lot of “Derby Rules” winning in only his fourth lifetime start and from post 20.


Florida Derby winner Vicar (1999) was clearly on the downward part of his form cycle after running a dull third in the Blue Grass in his final Derby prep. Regardless, it was tough to come up with the ex-claimer Charismatic as an alternative.

I had hoped Saarland (2002) would be the one to give the Phipps family and Shug McGaughey their first Kentucky Derby win, but that would have to wait 11 more years after this regally-bred colt proved he was indeed as slow as his form suggested (and at a ridiculously underlaid price of 6-1).


The 2009 Derby, contested over a sloppy track, was a veritable dart throw in my eyes. I simply didn’t like anybody, so I took a shot with Desert Party (2009), who had run well in the U.S. at two before wintering in Dubai, where he won two out of three. Ultimately proving to be more of a miler type, he looked more logical on paper than the horse who actually won – 50-1 longshot Mine That Bird.


When I’ve played chalk, it’s been Bob Baffert-trained chalk. In addition to Bodemeister and Point Given, I also backed the undefeated Indian Charlie (1998), only to see him run third to stablemate Real Quiet, whom he had beaten in the Santa Anita Derby. Like The Deputy two years later, Indian Charlie never ran again.

(Grindstone Photo: Skip Dickstein)