Our biggest Kentucky Derby heartbreaks

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TwinSpires Staff

April 21st, 2015

This week, we'll be strolling down memory lane to revisit several Kentucky Derbies that hold special personal meaning for us. Our second "team blog" looks back at our biggest Derby heartbreaks.

Vance Hanson: Have you ever been completely spot-on about a race and yet walked away with relative peanuts as a reward for your brilliance? For me, the 1995 Kentucky Derby was that race. That Derby was the first on which I could legally bet, and I went to the track feeling only three horses could win: Timber Country, Thunder Gulch, and Tejano Run. Timber Country was part of an entry with Serena's Song that was favored at 3-1, a price I wasn't about to take on a horse who had not looked all that progressive in his Santa Anita preps, and at the time no favorite had won the Derby since 1979. Thunder Gulch, like the entry, was trained by D. Wayne Lukas. The Florida Derby winner's dull fourth in the Blue Grass was excusable, but I have to admit his 24-1 price discouraged me. What could possibly be wrong with him? Tejano Run had placed in both the Jim Beam and Blue Grass and seemed to be sitting on a good race. He was the 8-1 fourth choice. As a high school senior with very limited betting funds, I had to make a decision. I seriously considered both the exacta and trifecta pools, but when push came to shove both wagers seemed too much to risk my small capital on. In the end, I bet my budget on Tejano Run in the win and place pools. As everyone knows, Thunder Gulch scored the upset with Tejano Run second and Timber Country third. A $2 exacta box, costing $12, would have given me a $480 return. A $2 trifecta box, also costing $12, would have returned $2,099.20. Tejano Run paid a measly $10.20 to place by comparison. Instead of proclaiming myself "King of the World" Andy Beyer-style, I was just the latest example that scared money never wins.


James Scully: I was sold on Silver Charm after the 1997 San Vicente. It was his first start since capturing the Del Mar Futurity and the gray colt rolled to an impressive win in a fast time. The performance led to a $50 Kentucky Derby wager, at 12-1 odds, while on a Las Vegas trip with friends in early March. Silver Charm proceeded to drop his final two preps, finishing a close second in both the San Felipe and Santa Anita Derby to Free House, who I readily admit to shortchanging at the time as well as dropping some coin on Silver Charm win bets. When I witnessed Pulpit capture the Blue Grass with ease, I officially abandoned ship. I touted the wrong horse on Derby week, with my tickets going into the garbage after Pulpit weakened to fourth, and Silver Charm finally came out on the right side of a close battle, repulsing the late run of Captain Bodgit to win in thrilling fashion. Some solace was to be found from the future bet, but the outcome really stung at the time because of my lack of faith in the future Hall of Famer.


Kellie Reilly: While I've suffered bitter disappointments in a few Derbies, the worst of them all came in 2001. A big believer in Point Given since his victory in the Kentucky Cup Juvenile the previous September, I was delighted with his development through the fall. Point Given's physique and pedigree both screamed classic contender, so whatever he did at two was a bonus. His progression from a second in the Champagne, to a flying near-miss in the Breeders' Cup Juvenile, to a score in the Hollywood Futurity only confirmed the idea. After the Bob Baffert star returned to dominate the San Felipe and Santa Anita Derby, I was convinced that this chestnut beast had all the tools to win the Triple Crown. In Tom Durkin's memorable phrase, I too was awaiting the "pent-up power of Point Given" as the field rounded the far turn at Churchill Downs through an insane Derby pace. But when Hall of Famer Gary Stevens sent him after stablemate Congaree, the response was lacking. My heart sank, stomach dropped, and I wilted helplessly as Point Given flailed down the stretch in fifth. Monarchos surged past him, and overwhelmed the unbelievably game but exhausted Congaree, to finish in 1:59 4/5 -- the fastest time since Secretariat's record 1:59 2/5 in 1973. Keeping faith in Point Given for the Preakness, I accordingly celebrated his emphatic rebound. Next came his 12 1/4-length Belmont rout, which ordinarily would have been cause for jubilation. Not this time. His supremacy was now bittersweet. This should have been a coronation. This should have been the exclamation point on the Triple Crown, ending the drought that endured through my living memory. Only he lost the Derby in by far the worst performance of his career, and there went the dream.


Jennifer Caldwell: Afleet Alex's third-place finish in the 2005 Kentucky Derby will go down as my biggest Derby heartbreak. I fell in love with the talented colt when he began his career as a juvenile and rooted him on every time he ran. After watching his tour de force in the Arkansas Derby three weeks before his trip under the Twin Spires I couldn't understand how he wasn't the favorite that day. Once the race started I kept my eyes on Afleet Alex and no other as he navigated his way four and five wide on the backstretch just behind midpack. My heart sped up as he split rivals and began rallying down on the inside, but my hopes were dashed when Giacomo and Closing Argument came running to nip him on the wire. The brilliant little bay would go on to prove himself in the Preakness, recovering to take the second jewel of the Triple Crown by 4 3/4 lengths after stumbling and going to his knees in the stretch when a rival came over and clipped heels. He ended up taking two-thirds of the Triple Crown when showing up three weeks later in New York to romp home a seven-length winner of the Belmont Stakes in his career finale.

Ed DeRosa: As Jennie Rees says, There are no bad Derbys -- some are just better than others. It's probably just the magic that surrounds America's best race, but it seems immune to suffering truly bad beats. The "luck" factor and randomness of a 20-horse race with all participants running further than they ever have before in front of more people than they'll ever see is a factor as well. We've all said "that's racing before," but this race takes it to the extreme. "That's the Derby for you." So was I heartbroken when Mine That Bird beat my top choice Pioneerof the Nile in the 2009 Derby and I was left to wonder "what if" I had spent an extra few bucks to wheel my pick top and bottom in the race? Not really. A horse I gave no chance to win won, so I was OK with not winning too. Buy the ticket, take the ride and all that. Was I heartbroken when I'll Have Another won the 2012 Kentucky Derby after weeks of telling people he was my pick before switching to Hansen the week of the race? No. It sucked not to get the glory of picking a $30 winner on top, but I still made him my second pick and did well on the futures. It stung more that Bodemeister, who I didn't like at all as the favorite, finished second. Unfortunately, the undercard races are not immune to breaking my heart, and none was the case more than in 2010 when General Quarters won the Woodford Reserve Turf Classic sandwiched between two Calvin Borel victories. I gave General Quarters very little chance and bet accordingly, singling Churchill Downs Stakes winner Atta Boy Roy at 10-to-1 on a main Pick 4 play that fanned. Mona de Momma kicked things off with a $19.20 score in the Humana Distaff and Super Saver would have capped a $36k Pick 4 had I fanned wider in the Turf Classic, but instead of fanning wider I whiffed.