Looking Back on the Last 15 Kentucky Derby Days

After this weekend’s Wood Memorial, Santa Anita Derby and Illinois Derby results, the race for the roses is heating up. This is one of my favorite times of the year, as the weather starts to improve, the days get longer and the ponies head into the gate with a shot at history in one of the greatest events in all of sports, the Kentucky Derby. As I try to sort out the contenders and pretenders, I thought it might be a good time to be a bit sentimental and look back at the horses that I have picked to win the last fifteen Kentucky Derbys. Hopefully this will help me to notice some of the mistakes I’ve made and highlight the things I saw correctly, and also serve as a trip down memory lane.

The first Kentucky Derby I ever picked was in 1994, when my best friend insisted that I get into the sport of horse racing and pick a horse to root for. I went with Strodes Creek, who finished a non-threatening but impressive third, and I was immediately hooked. I managed to correctly pick the late Tabasco Cat, one of my all-time favorites, to win the next race, the Preakness, and the rest, as they say was history. Here are the horses that I picked over the next fourteen years:

1995: Thunder Gulch. This was my first ever correct Kentucky Derby pick, and I wish I would have been of legal age to gamble, since Thunder Gulch went off at 25-1, a price that I vividly remember being shocked by. I won a bit of money in a pool that year, but certainly have never liked a horse to win with odds that high during any of the years that I could actually bet the race at an OTB. Let the record show that I also correctly predicted Timber Country to win the Preakness and stop Thunder Gulch’s quest for the Triple Crown.


1996: Cavonnier. Of all the Kentucky Derbys I would incorrectly pick after this one, I don’t think any have ever been as painful as this one was. Cavonnier started knocking off horses at the top of the stretch, and I was feeling like a genius. It looked like Cavonnier had the race won, until another hard closing horse, Grindstone, came motoring down the stretch (seemingly out of nowhere) and nailed my horse at the wire in a photo finish. My dear friend Pam watched the race with me that day and had Grindstone for the win, and hasn’t let me forget it to this day. Oh, the misery!

1997: Captin Bodgit. After 1996 ripped my heart out, 1997 had more pain in store in one of the greatest Kentucky Derbys ever run, as I lost my second straight photo finish after Silver Charm nipped both my horse and Free House in an incredibly memorable finish. I got my revenge on the winner when I correctly picked the deep closer Touch Gold to win the Belmont and stop Silver Charm’s quest for the Triple Crown.

1998: Real Quiet. I got back on track with this pick. I recall loving the way Real Quiet closed in the Santa Anita Derby while finishing second to the Derby favorite, Indian Charlie, and he ran and won the Derby exactly the way I had envisioned. Real Quiet went on to win the Preakness before losing a heartbreaker in the Belmont to the horse that I again picked to stop the Triple Crown run, Victory Gallop.


1999: Menifee. I have to say, the races that I was wrong about early in my picking career would have still made me a lot of money on my place bets. Here, I lost my third Derby in four years by a photo finish (okay, I lost by a neck this time). How is that even possible? Charismatic went on to win the Preakness, but failed to capture the Triple Crown, finishing third due to injury in the Belmont.

2000: Fusaichi Pegasus. In all my years of picking Kentucky Derby winners, I don’t think I was ever as confident that my pick was correct as I was about FuPeg (well, maybe in 2003, but we will get to that later). If you ask me, the loss to Red Bullet in the Preakness and subsequent disappearance from the form he showed early in the 2000 season remains one of the most perplexing things I’ve ever seen in horse racing. This horse was a true monster. It was nice to be right again, even if for the first time ever, I won with the favorite.


2001: Monarchos. By far the most thrilling Kentucky Derby victory of my life. Everyone and their mother was all over the superior talent Point Given in this race, but I’d had my eye on this gray colt early on and loved his closing style. I watched the race unfold as I predicted with the girl I was dating at the time (who looked on in utter fascination) from a hotel in downtown Indianapolis, I felt on top of the world with this pick. On my college budget, my $20 place bet returned over $100 and paid for our dinner that night. As a sidenote, when my parents leased me a brand new silver Alero that summer, I named it Monarchos.


2002: Perfect Drift. I had absolutely no confidence in this pick, but still didn’t see the race unfolding as a wire-to-wire win by the frontrunning Illinois Derby winner War Emblem, and this was a rare Derby indeed. Perfect Drift went on to run until the elderly age of nine and became an all-time favorite of mine, continuing to be a factor to hit the board in every race he ran for the next six years after his third place showing here. As a sidenote, my miss here started a long cold streak.

2003: Empire Maker. Going back to my 2000 FuPeg pick, which I was as confident as I’ve ever been in picking a Derby winner, I can’t help but admit I thought I had this one in the bag. This was automatic money. And, this was also the only time I can recall my human being spread across the carpet of my 900 square foot Lakeview apartment in the middle of the day pleading, screaming, completely in all-out disbelief of what was occuring before my eyes. Funny Cide? Really? The gutsy gelding? Sorry, but if you picked this one and beat me, you were very, very lucky. Empire Maker was a superior horse, and proved it when he spolied Funny Cide’s absurd quest to win the Triple Crown. Hopefully I don’t have to tell you who I picked to win that Bemont. Sorry, I’m going to be bitter about this one until my death.

2004: The Cliff’s Edge. In the midst of my long drought of accurate Derby picks, I started to get a bit “cute”, “trendy” or whatever you might call it. I started avoiding the horses that had proven their speed and started looking instead at value horses that I thought had closing speed (thank you, Real Quiet and Monarchos). As a result, I overlooked what was clearly the best horse in this particular race, and the best shot at the Triple Crown that we ever had this decade, Smarty Jones. By the time the Belmont came around, I’d flipped, and was all in for Smarty, but as the racing gods would have it, he too was nipped at the wire by a horse named Birdstone, son of Grindstone, who as you recall nailed me in 1996. This is a cruel game. For the record, if you’re paying attention, this was the first time in eleven years of Derby picks that the horse I picked failed to hit the board, as The Cliff’s Edge finished fifth without much running room. After the field expanded to 20 horses in the coming years, this became a much more difficult accomplishment to uphold.

2005: Bandini. This was the first Kentucky Derby that I ever attended in person, and while I had a great time, I didn’t ever feel very good about my pick, but found it to be the best of a weak crop of three-year-olds that had no standout. I suppose I liked his stalking style, and to an extent, his name (this shows you how far off I had become at this point in my drought).  The horse to beat was Bellamy Road, Steinbrenner’s superhorse who had posted a 117 Beyer in the Wood Memorial- a figure unheard of for horses in this early portion of their campaign. I was correct in taking a stand against that one, who finished up the track in seventh. Many consider this Derby to be a complete throwout, as 70-1 rabbit Spanish Chesnut scalded the field in ridiculous fractions before fading and leaving only the plodders. Giacomo closed to win at 50-1, while the aptly named Closing Argument grabbed second at 70-1 to create the largest Derby exacta of all time ($9,814 for a $2 bet). Bandini’s 19th place finish was unprecedented for my picks, and will surely take me to my grave as my worst Debry pick ever, by far. Nevertheless, I never in a million years would have picked Giacomo to win this race and don’t regret it; the scene at the track after he won was like someone had died, and I’ll never forget it. But I do wish that in losing I had picked a real horse with stength and courage, like Afleet Alex, who finished a threatening third before winning a memorable and heroic Preakness (I had him) and then the Belmont.

2006: Point Determined. At this point, I think that I had completely lost all of the subtle intricacies of handicapping that had made me so successful in my teens, and started relying on ridiculous methods like pedigree assessment, closing speed figures, and trend recognition. I didn’t like Barbaro here because he hadn’t run in seven weeks, and as we all know, the layoff didn’t make much difference, except for Barbaro to post the biggest Derby romp in modern history. A ninth place finish here for my pick bettered my 2005 disaster, but I should have been wiser. Being a fan of the sport above all else, I became a huge Barbaro fan, and was heartbroken when I watched his Preakness debacle, and ultimate demise, on live television two weeks later. I still contend that this was the greatest horse racing tragedy of my lifetime, and moreover, that if he had finished the race in tact, he still stood no chance against the winner, Bernardini.

2007: Street Sense. This is easily my second most glorifying moment; aside from the fact that my horse came out of nowhere to win this race on the rail, but also that I was in the infield at the time, and in my drunken state managed to taunt an elderly hillbilly woman who had assured me that Scat Daddy would win (he finished 18th, and was never a factor). This was a great race and a great class of three-year olds, including eventual world-beater Curlin, who came back to win the Preakness and lose the Belmont by a nose to a filly, but also horses like Hard Spun and Any Given Saturday, who should pull huge breeding fees in their own right. In any event, it felt good to bust the slump live in such dramatic fashion.

Kentucky Derby Horse Racing

2008: Colonel John. I still stand by this pick and don’t put it in the “cute” category, even though in retrospect it was fairly obvious I suppose that Big Brown was going to win this race. Still, I was a huge Tiznow fan and looked forward to the Colonel’s up-move on the dirt, which he eventually realized– I’d take Colonel John again right now in his current form in a 10f race over the retired Big Brown. The Colonel finished fifth before taking the rest of the spring off, but came back to win the Travers later that year at the same distance.

So, for those of you counting, here are my stats after 15 years of Derby picks.

1st place: 5

2nd place: 4

3rd place: 2

4th-10th: 3

worse than 10th: 1

Not bad I guess.

2009: Yet to be determined, but I think this is a strong class with about eight horses that have a good chance to win.

1. I Want Revenge: (Stephen Got Even- Meguial/ Roy) He posted a 103 Beyer in that gutsy Wood Memorial win, and rest assured that figure would have been larger if he’d had a better trip, to say the least. He didn’t need to win that race, and still did pretty easily under huge adversity, stumbling at the start and basically spotting five lengths to the field. He moved up in a big way after moving from synthetic to dirt in the Gotham where he posted the highest Beyer fig of any of these at 9f. Appears he came home in roughly :12.1 in the Wood, proved he can win from anywhere, and overall looks versatile and suited for the distance. 113 Beyer at 9f.

2. Quality Road: (Elusive Quality- Kobla/ Strawberry Road) Trying to avoid making the same mistake I made last year, as this one looks like the one to beat, though I still have distance questions based on his running style and pedigree. He caused a stir early this week as news of a quarter crack broke, which while it appears to not be too severe, just adds one more variable. He’s an impressive physical specimen who could get loose on the lead, and his come home time of :12.2 in the Florida Derby isn’t too shabby either. On paper, looks like the one to beat. 111 Beyer at 9f.

3. Dunkirk: (Unbridled’s Song- Secret Status/ AP Indy) His late move in the Florida Derby was the most impressive of all (about :23.0 for 2f), but he couldn’t hang on and looked tired through the stretch. Still, he had a wide trip and should move up from that effort, if he gets in with only $150,000 of graded earnings. Lack of seasoning is a concern, but pedigree should be there on his mother’s side despite the shortcomings of his sire. 108 Beyer at 9f.

4. Pioneer of the Nile: (Empire Maker- Star of Goshen/ Lord at War) He has done nothing wrong, and is a professional act. His pedigree says he should thrive at 10f , but his running style and speed figures say otherwise, although he has yet to race on a dirt surface. He looked a bit rank in the Santa Anita Derby, but eventually settled in and managed to win impressively. So far he hasn’t faced enough true pace to benefit his running style which was clear in that win, but my main concern with him is that he hasn’t raced on dirt yet and that his speed figures are lower than the rest of these. Reminds me a bit of Colonel John last year.  96 Beyer at 9f.

5. The Pamplemousse: (Kafwain-Comfort Zone/ Rubiano) Nothing about his pedigree indicates that he should be winning races at 9f, let alone 10f, but he’s been burying foes on the lead on synthetic surfaces. His scratch from the Santa Anita Derby earlier today leaves some questions to be answered, and I typically never like horses of this style for the Kentucky Derby, but if this is a year for a front runner to get loose and win, this is the guy. Best name ever, I might add. 103 Beyer at 9f. UPDATE: The Pamplemousse is now off the Derby Trail due to injury.

6. Desert Party: (Street Cry- Sage Cat/ Tabasco Cat) His second place finish in the UAE Derby probably just created more value for this one. I generally don’t bet on the Godolphin horses for personal reasons, bit I can’t dismiss solid value when it’s there. As I mentioned much earlier, I love his damsire. And, his UAE Derby performance was better than it looked, as this closer was tricked by a slow pace, and still came home in :12.2 for the final furlong. Don’t dismiss, especially in the slop.

7. Chocolate Candy: (Candy Ride- Crownette/ Seattle Slew) Yes, you read that right, his damsire is Seattle Slew. He’s demonstrated a strong closing style and the combination of those two facts is downright scary; this is a horse waiting in the weeds for a pace breakdown a la 2o05. Still waiting on his Beyer for the Santa Anita, but I’ll estimate it at about 95 based on Pioneer of the Nile’s number. The main concern is that he is just too slow to hit the board. So was Giacomo though. 95 Beyer at 9f

8. Friesan Fire (AP Indy- Bollinger/ Dehere) This might be the horse that I’m underrating the most, but he’s bascially a throwout for me based on the odds he’s likely the require. He’s never run past 8.5 f. And isn’t AP Indy older than Dehere anyway? That’s some messed up family dynamics around the horsey Christmas tree. In all seriousness, he loves the slop, so if the Derby isn’t a fast track (never happens; I was there two years ago in a 4-inch downpour and an hour of sunlight turned the track fast), take a shot I guess. I’ll never pick a horse to win the Derby that hasn’t gone 9f. You can put that in writing.  104 Beyer at 8.5

Others: Old Fashioned (early fave, can’t get the distance though); Win Willy (Monarchos colt, might have closing speed, stay tuned for Arkansas Derby); Musket Man (stalker, won Illinois Derby handily but slowly, having trouble getting excited about him); West Side Bernie (impressive in Wood, has staying power). Toss the rest! (for now): Square Eddie, Terrain, Mafaaz, Hold Me Back, Regal Ransom, Giant Oak, Papa Clem.


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