Derby Sommelier: Finding a Derby For Every Fan’s Taste

There are no uneventful runnings of the Kentucky Derby, and even if there were, the event would never be such a monumental waste of time that a viewer could be angry about it. Baseball fans can gripe when 20 or more hours of buildup results in an anticlimactic World Series sweep, and any amount of time watching a Super Bowl featuring Tom Brady passes like dental surgery for football fans in New York. The greatest event on the horse racing calendar is two minutes long, and it’s often filled with more excitement than some sporting events fit into hours or days. It’s perfect.

Even still, fans of horse racing grow to love the sport in different ways, and certain runnings of the race appeal more to some than others. Some like the dominant wire-to-wire performances while others like when horses come from out of the clouds. Others like stretch duels and long shots, while more casual enthusiasts are interested in the party in Louisville. 

That’s where Paddy’s Picks comes in. Some might say that I have wasted my time watching 40 Kentucky Derbies straight and doing several hours of research thereafter, but I would argue that there are far worse ways to waste one’s time. I’ve looked through four decades of Derby history to find the very best for fans of different backgrounds. The categories aren’t mutually exclusive, nor do they encompass every single racing fan, but give me a break. I’m busy here.

As the 2021 Derby draws ever nearer, it’s important to look back and appreciate what has come before. I hope to have provided ample opportunity to do so below.

Triple Crown Dreamers (1973, 1977, 1978, 2015, 2018)

Every year, the number of potential Triple Crown winners drops from thousands to 20 in late April. On the first Saturday in May, that number drops to one, as the Derby winner carries on his quest for immortality alone. Many have tried but few have pulled off the three wins necessary, but every champion since 1973 has started in Kentucky.

“Maybe this is the year,” they say. Some Derby winners even go on to win the Preakness, and the dreams grow more vivid. As Real Quiet turned to the Belmont grandstand in 1998, it seemed like a certainty. But since Secretariat won in 1973, only four other horses have pulled off a feat that has gone through phases of impossibility. It’s dangerous to dream in horse racing, but every year, many fans go back to the Derby wins of legends in the hopes of manifesting another hero.

Long Shot Hunters (1999, 2005, 2009)

Long shots in the Derby have fallen by the wayside in the past decade, and while Country House’s 2019 victory at 65-1 certainly qualifies, it came via disqualification and is therefore somewhat unsatisfying. For some truly thrilling upset victories, three candidates stand out in relatively recent history.

The story of Charismatic in 1999 is inextricably tied to jockey Chris Antley. After becoming one of the most successful riders in the country in the early 1990s, Antley retired in 1997 to deal with a serious drug and alcohol addiction, as well as a weight problem. He returned to action in 1999, and legendary trainer D. Wayne Lukas took a risk and gave the rider a second chance on his 31-1 shot. 

When Charismatic won by a desperate neck, thanks in large part to a stellar trip provided by his jockey, it meant redemption for an overlooked horse, his aging trainer and a jockey that everyone had counted out. Antley’s premature death in 2000 will always cast a shadow over this victory, but it will forever commemorate the talent of one of the greatest jockeys of the era.

In 2005, many experts had narrowed down the Derby field to two horses: Bellamy Road and Afleet Alex. Bellamy Road, in particular, was being hailed as the next superhorse after a dominant win in that year’s Wood Memorial Stakes. At 50-1, Giacomo went unnoticed by most after losing five straight races leading up to May. TVG analyst Ken Rudolph had other ideas.

The behind-the-scenes video of Rudolph watching the race at the TVG desk is one of my favorite pieces of horse racing media. The analyst had taken every opportunity to mention his long shot and doubtlessly had a large wager in place as well. The video of his reaction is the purest form of handicapping culture that I’ve ever encountered, and anyone with a live long shot this year may just feel the same way.

Meanwhile, a large number of people my age will remember Mine That Bird as one of the first Kentucky Derby winners they remember watching live. My earliest Derby memory is Big Brown’s victory in 2008, but I prefer the 2009 running in every way. Jockey Calvin Borel gave the 50-1 shot one of the greatest trips in Derby history, weaving back and forth between horses to score the massive upset going away. The colt’s acceleration along the rail was completely lost on legendary track announcer Tom Durkin, who certainly had better moments as the long shot powered home as much the best.

Historians (1976, 1979)

Racing fans don’t have to go far to find exciting renditions of past Derbies, but as a result, they tend to forget several long past Derbies worthy of remembrance. Two particular races from the late 1970s stand out as special events overshadowed by more important racing events of the era. The 1976 Derby featured a thrilling stretch duel between Bold Forbes and Honest Pleasure but seldom receives recognition. 

Even more unjustly, Spectacular Bid’s Kentucky Derby victory is all but an afterthought as it happened one year after the back-to-back Triple Crown victories of Seattle Slew and Affirmed. If not for an injury before the Belmont Stakes, he very well could have made it three straight, and if one were to compare the careers of the three horses, they’d discover that the superhorse duo was actually a trio.

Women and Other Sensible Racing Fans (1980, 1988)

Only 10 fillies have run in the Kentucky Derby since 1980, but two of them won. This is a frustrating statistic because while the Kentucky Oaks, the all-female, less hyped equivalent of the Derby, is often much slower, there are occasions when the winners of the two events are comparable. In 2009, Rachel Alexandra was actually faster than Mine That Bird and proved it in the Preakness next time out. I’m not calling for full integration, because it’s true that the best fillies at this age and level are traditionally slower than the best colts. I just think that more trainers should take the chance that these two took. The notion that fillies can’t compete with colts is preposterous.

In 1980, Genuine Risk beat favorite Rockhill Native and the rest of the boys at 13-1, becoming the first filly to run in the Derby since 1959 and the first to win it since 1915. She went on to finish second in both the Preakness and Belmont Stakes. 

Eight years later, Winning Colors defeated an extremely talented field that included Forty Niner, Risen Star and Seeking the Gold. She later finished second after a thrilling duel with Personal Ensign in the 1988 Breeders’ Cup Distaff.

Adrenaline Junkies (1985, 1996, 2012)

These three races aren’t particularly important to the history of racing. They’re just a ton of fun to watch. I will limit my commentary on them because they don’t need much help.

Spend A Buck runs them off their feet in the 1985 Kentucky Derby.

Grindstone vs. Cavonnier in a photo finish in the 1996 Kentucky Derby

I’ll Have Another vs. Bodemeister in the 2012 Kentucky Derby

Fans of Tom Durkin and Superior Commentary (2001, 2003, 2004)

Yes, I’m from New York, and yes, I like my hometown commentators more than most. Gary, Keith and Ron are the best broadcasting team in baseball and Tom Durkin is the greatest track announcer to ever live. That’s the way it is. For anyone who agrees, I refer them to the Derbies of the early 2000s, when Durkin delivered multiple broadcasts that simply made the races better. Horse racing is more dependent on good announcing than nearly any other sport out there, and Durkin was perfect. His stretch calls in 2001, 2003 and 2004:

2001: “Record time here in the Derby, we’re at the top of the stretch and it is Congaree who is full out. Here comes Monarchos under a heavy drive on the far outside! Invisible Ink is there, Point Given not today. One furlong left, here comes Monarchos, who sweeps to the lead! He’s pulling away by two, he’s pulling away by three! Jorge Chavez and Monarchos have won the Kentucky Derby, and the final time was 1:59 ⅘ seconds! He was as fast as Secretariat!”

2003: “They’re coming down to the final furlong and the gutsy gelding Funny Cide has a narrow lead! Bobby Frankel’s Derby duo, Peace Rules to his inside, Empire Maker giving it all! Funny Cide trying to pull off the upset here, 12-1 coming down to the line! And the gutsy gelding Funny Cide has won the 129th Kentucky Derby!”

2004: “Lionheart turns for home, and undefeated Smarty Jones comes wide off the turn and these two hook up at the top of the stretch! Lionheart is all heart, Smarty Jones is all out, and those two deadlocked at the eighth pole! And Smarty Jones is roused to the lead by journeyman jockey Stewart Elliott and they have taken the lead away from Lionheart. Farther back, it’s Limehouse and Imperialism, and here is the first undefeated winner of the Kentucky Derby since Seattle Slew in 1977!”

Readers and Drinkers Alike (1970)

By most accounts, the 1970 Kentucky Derby was unremarkable in comparison to some of the more well-remembered runnings later in the decade. The fact that Dust Commander won in an upset is largely inconsequential to anyone who didn’t profit from it, and if not for a single individual’s attendance at the festivities that day at Churchill Downs, the race would have little relevance to me at all.

It took a long sequence of events for legendary writer Hunter S. Thompson to end up in Louisville on the weekend of May 2, 1970. A last-second decision by Scanlan’s Monthly editors to cover the culture and people at the Derby led to a scramble that put the upstart writer in the thick of his hometown’s rowdiest day. Several weeks later, the events of that weekend inspired one of his most famous pieces, “The Kentucky Derby is Decadent and Depraved.”

The article is officially credited as the first example of gonzo journalism, in which the reporter is often a part of the story and the events are depicted subjectively. Thompson portrayed his adventures that weekend in all their excessive glory in the pages of Scanlan’s Monthly, complemented perfectly by Ralph Steadman’s illustrations. He pushes any moment of reflection further and further out of sight as he continues to lose control, until a single glance in the mirror becomes a gut-wrenching realization for a man in disarray.

Any attempt to recap the piece further would be a disservice, but I’ve read it in its entirety at least 10 times since I first discovered it as a senior in high school. To those among you who find value in my recommendations, there are few pieces of writing I could possibly praise more highly.

Link to Story: http://brianb.freeshell.org/a/kddd.pdf

Patrick Moquin Sr. (2011)

I don’t know what kind of backward church schedules a communion on Kentucky Derby Day, but on the first Saturday in May before my 11th birthday, I was with my family in Connecticut celebrating a cousin’s Holy Sacrament. My mother was at her most gracious that day and my sister played well with the other kids unless we were roughhousing. My father was there too, and I don’t want to make it seem like he was unsociable, but he may have been a little preoccupied. 

Between the three-hour drive, 90-minute ceremony and all-day festivities, I’m not sure how he found the time to spot Animal Kingdom as a potential long shot in the Derby. I could’ve taken the month and wouldn’t have come up with it. The Graham Motion trainee had never run on dirt before and only qualified for the race after a victory in the G3 Spiral Stakes. 

I don’t even know how he got the bet in, but as I’ve grown ever so slightly wiser to the racing world over the years, I’ve learned that racing fans can move mountains for 21-1 odds on a horse they love. For a half-hour before dinner, a small group at the party (my father, a few older cousins and myself) commandeered the television for the racing event of the year.

My father and I love horse racing in different ways. Sure, we share the same adoration for Belmont and Saratoga, and we love when an early speed duel sets up for some closers. For him, though, no race is more important than the one on the next page of the racing form. Names of horses become fuzzy soon after they run, and favorites are always, always beatable. There are no “heroes” in racing, because “heroes” don’t usually pay much. It’s true that this sport disappoints the optimists more often than not, but I think it has its moments too.

For all of his realism and resistance to the hype, my father sure loved Animal Kingdom that day, and if you ask him about it now, I can guarantee that it’s a name he hasn’t forgotten.