A Decade of Derbies

“Who’s your Derby horse?”

The question is on everyone’s lips (and fingers) this time of year, with prep season complete and only a few short weeks left until the big dance. Obviously, most horseplayers have a shortlist of contenders that they think could win the Kentucky Derby; by the time the race runs on May 7th many of us will have determined which horses to use in multi-race wagers, which horses have a chance to round out exactas and trifectas, and which horses to take a stand against. Yet, despite the fact that most handicappers will have money on more than one of the twenty three-year-olds in the 142nd running of the historic classic, it’s nearly mandatory that racing fans have one horse they deem their Derby selection. Listening to Jason Beem discuss his five worst Kentucky Derby picks got me to thinking about my Derby selections during my time as a horse racing fan, which I’d like to recount here today.

My first ever “Derby horse” was Sinister Minister in 2006, and I can’t help but laugh at my 12-year-old self for thinking he had any sort of legitimate chance. I had seen his Bluegrass and was immediately on the bandwagon. I THINK he had hit the rail in one of his prior preps and that I decided that was a sign he was maturing at the right time, since he ran straight in the Bluegrass. I was oblivious to the notorious speed bias of Keeneland’s surface at the time. Needless to say, I believe he finished 16th and it was back to the drawing board for me.

I did better in 2007, I suppose, since my pick finished 6th that year. I had been on the Circular Quay bandwagon since he was a 2-year-old, and I guess leading up to the Derby he performed “okay” enough to keep me from jumping ship. Who knows, either way, it was another off the board finish.

In 2008, I was all about Pyro. I threw out the Bluegrass because I figured it was irrelevant to the Derby, and I was adamantly against Big Brown because he had never been tested in a race – a common angle in my Derby handicapping, and one that has served me well since, but one that doesn’t apply when the competition is just THAT inferior. Pyro finished 10th, while Big Brown went on to dominate in the Derby, Preakness, and Haskell.

I made a list of Derby horses, rating them from top to bottom in 2009, with a comment for each. My #20 was Mine That Bird, with the comment “doesn’t belong.” Strangely, I don’t remember who my #1 was. I know I liked Dunkirk going into the race because of the tenacity he showed versus Quality Road in the Florida Derby, but felt he might be too immature. My big long shot pick was probably my worst since Sinister Minister – although he actually did finish ninth – in West Side Bernie, another horse I had liked since he was two and somehow convinced myself was still logical. I think I ended up going with the public on Friesian Fire as my top pick because of his freaky off track performances in Louisiana. I’m pretty sure he was last.

Super Saturday 2010

16-year-old Jess at Belmont Super Saturday in 2010… because that’s the most relevant photo I have

I honestly don’t remember a whole lot of what I thought going into the 2010 Derby – I had to look up the chart just to remember who ran. I know that Super Saver was on my short list because of his potential to love a wet track, but he definitely wasn’t my top pick that year. I think that role went to the filly Devil May Care. I do remember my “residual 2yo choice” was Backtalk, although I had by that point wised up to my tendencies and didn’t actually think he would win. Good thing, too, since he was last. The one thing I do remember is being devastated when Uncle Mo scratched, because I was so excited to bet against him in the Kentucky Derby. He was the untested “super horse” type that I was always so keen to play against, and when he defected from the Derby, he took with him the only valid opinion I had that year.

I could have never had Animal Kingdom in the Derby, although I was firmly on the Shackleford bandwagon after what I thought was a valiant effort that day, an opinion that paid off two weeks later. 2011 was the first time my Derby pick hit the board, however, as I was all about Mucho Macho Man going into the race. Ironically, I would go on bet against Mucho Macho Man in pretty much every race he ran afterwards, often to my detriment.

I will admit that up until May 5th, 2012, I liked Gemologist. I was wary of him until his Wood Memorial, which I thought was a super gutsy and impressive effort. It was only at the last minute, when it came time to actually bet the race, that I switched trains. I’ll Have Another looked like a million bucks in the paddock and post parade, and I couldn’t believe the 15-1 odds on a horse that had done nothing wrong in his career. Even in defeat, he had always made a good showing of himself, and I felt that his style would suit the Kentucky Derby far more than the style of a horse like Bodemeister – who I didn’t even think would GET the lead with the likes of Trinniberg and Hansen in the race, much less hold on to get beaten less than two lengths. Despite being wrong about the runner-up, however, I had finally picked my first Kentucky Derby winner.

The 2013 Kentucky Derby was particularly thrilling for me. I spent the summer of 2012 as a press box intern for NYRA at Saratoga, an experience I will forever cherish. On the afternoon of August 18th, I was handicapping as usual, and, as usual, my interest went first and foremost to the two-year-old races on the card. As a pedigree nut, I love delving into the bloodlines of promising youngsters and picking out the particularly interesting ones to keep an eye on. I had already dialed in on a first time starter for Shug McGaughey. The Malibu Moon colt was out of Lady Liberty, who traces tail-female to Laughter, a 3/4 sibling and the only sister to the immortal Ruffian. With Laughter’s other descendants including the likes of Private Terms and Coronado’s Quest, the colt’s breeding was promising. I kept a keen eye as the Phipps/Janney owned colt broke awkwardly but recovered to rally strongly for 3rd.

“That Shug colt could be a good one once he figures out what he’s doing,” I remarked to my fellow interns following the race, and promptly added “Orb” to my Equibase watchlist. Of course, I didn’t really think I had just seen the next Derby winner, but perhaps a nice stakes winner somewhere down the line. Fast forward to the following spring, and Orb winning the Fountain of Youth and Florida Derby, and I was firmly on board, convinced this wasn’t another Circular Quay or West Side Bernie, but a legitimate Derby contender. Sure enough, Orb pulled through as both my logical and sentimental selection in the race. The story would come full circle – no pun intended – when I got to see him at Saratoga multiple times that summer.

Orb - 2013 Saratoga Work2

Kentucky Derby winner Orb galloping at Saratoga’s Oklahoma training track in 2013

While handicapping the 2014 Kentucky Derby, I did everything in my power to find an alternative to California Chrome. I watched back tapes of every one of his races, trying to find a chink in the proverbial armor of the prohibitive favorite, but the more I watched, the more convinced I was that he was the real deal. I actually had to look up the race chart just to remember who else ran in that Kentucky Derby, and I do recall liking Samraat a little bit, and was curious about Danza, but in the end I landed on the chalk, and he won the way he had been expected to.

Last year was a similar story, although I was less skeptical of American Pharoah than I had been of California Chrome. The way that horse moved just blew me away from the time he first burst onto the scene in the Del Mar Futurity, and it seemed that everywhere you looked, horses he had soundly defeated were coming back and winning big races. Dortmund was the one horse I thought might be able to give Pharoah a run for it, with the tenacity he had proven but that his stablemate had yet to need. I managed to hit my first Kentucky Derby trifecta in 2015, keying the Bob Baffert duo on top with Firing Line and Upstart (who was last…) underneath.

Now here we are, ten years after naive little Jess watched Sinister Minister set the pace and fade badly, and the pressure is on to pick my 5th consecutive Derby winner. At this point in time, I am firmly in the Nyquist camp. As much as I felt Uncle Mo was overrated, I feel his son is the real deal. Many people are citing distance limitations as a reason to be wary of Nyquist, but I see no such problem. Uncle Mo was a speed horse who used a lot of mental and physical energy in his races, whereas Nyquist has the mind of an absolute professional. He has proven that he can be flexible in his running style without freaking out or exerting any more energy than necessary. He’s overcome difficult trips and various pace scenarios, and emerged victorious every time.

Of course, there’s still plenty of time for things to change, and Derby week workouts are always a useful handicapping tool, but as things stand now, I’m expecting a fourth straight Kentucky Derby favorite to take the roses.


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