Using History as a Guide to Handicapping the 2021 Kentucky Derby

The Kentucky Derby field races past the finish line for the first time in the 2016 edition of the run for the roses. (Eclipse Sportswire)

There isn’t a horse race anywhere in North America — and maybe even the world — that receives more annual scrutiny than the world-famous Kentucky Derby Presented by Woodford Reserve at Churchill Downs. Considered to be “the most exciting two minutes in sports,” the Kentucky Derby pits 20 lightly raced 3-year-old Thoroughbreds against each other in a battle for supremacy on the first Saturday in May.

Each year, handicappers spend months analyzing the top contenders for the historic race, which has been held every year since 1875. And once the field is set, they pour over historical data, looking for trends to aid their handicapping.

Picking the winner isn’t just a matter of bragging rights — there’s great money to be won. Bettors who correctly selected the first four horses across the 2005 Kentucky Derby finish line were rewarded with a payoff of $864,253.50.

Not sure where to begin in analyzing the Kentucky Derby’s historical data? We’ve got you covered! We’ve put together a dozen trends to help point you toward the winner of racing’s renowned run for the roses.

Speed horses have an advantage

In the not-too-distant past, horses could come charging from just about anywhere in the pack to win the Kentucky Derby. But times change, and in recent years, the Derby has strongly favored horses with enough tactical speed to work out clean trips on the front end.

Case in point? Between 2014 and 2020, six out of seven Derby winners prevailed by setting or tracking the pace from no farther back than third place. In addition, pacesetter Maximum Security famously crossed the finish line first in the 2019 Derby, only to be disqualified for causing interference on the far turn.

The takeaway? Don’t assume the 1 1/4-mile distance of the Kentucky Derby will give an edge to late runners. Recent history suggests horses with tactical speed have a substantial advantage in the run for the roses.



Position after first 1/2-mile

½-mile & ¾-mile times



1st by 1 length (15 starters)

46.41, 1:10.23 (fast)


Country House

8th by 4.75 lengths (19 starters)

46.62, 1:12.50 (sloppy)



2nd by 0.5 lengths (20 starters)

45.77, 1:11.01 (sloppy)


Always Dreaming

2nd by 1 length (20 starters)

46.53, 1:11.12 (wet fast)



2nd by 4 lengths (20 starters)

45.72, 1:10.40 (fast)


American Pharoah

3rd by 2 lengths (18 starters)

47.34, 1:11.29 (fast)


California Chrome

3rd by 1.5 lengths (19 starters)

47.37, 1:11.80 (fast)



16th by 18.75 lengths (19 starters)

45.33, 1:09.80 (sloppy)


I’ll Have Another

7th by 8 lengths (20 starters)

45.39, 1:09.80 (fast)


Animal Kingdom

10th by 6 lengths (19 starters)

48.63, 1:13.40 (fast)

Look for horses capable of finishing strongly

Horses who have shown the ability to finish fast at the end of a two-turn route race have the best chance to handle the Kentucky Derby’s testing 1 1/4-mile distance. When analyzing Derby contenders, look for horses who sprinted the final three-eighths of a mile in :38 seconds or less — we’ve compiled a handy chart to help you out.

The data is strong: 18 of the last 23 Kentucky Derby winners successfully shaded the :38 mark in their final prep race, suggesting the ability to finish strongly is critical for success on the first Saturday in May.

Derby contenders who finished their final prep in :38 seconds or less: Essential Quality, Highly Motivated, Known Agenda, O Besos, Hidden Stash, Soup and Sandwich, Hot Rod Charlie, Midnight Bourbon, and Like the King.

Favor California shippers and the Florida Derby winner

Horses based in California have outperformed all others in recent renewals of the Kentucky Derby. Six of the last 10 Derby winners (Authentic, Justify, Nyquist, American Pharoah, California Chrome, and I’ll Have Another) spent the winter in California and completed the majority of their training at Santa Anita Park, though Authentic, Nyquist, and American Pharoah did race outside of California prior to the Derby.

Over the last decade, California has also produced Kentucky Derby runners-up Exaggerator (2016), Firing Line (2015), and Bodemeister (2012), plus third-place finishers Battle of Midway (2017) and Dortmund (2015). It’s safe to say 3-year-olds based in the Golden State warrant extra respect in the run for the roses.

Yet the single most productive prep race on the Road to the Kentucky Derby has undoubtedly been the Florida Derby at Gulfstream Park. Over the last 15 years, Barbaro (2006), Big Brown (2008), Orb (2013), Nyquist (2016), and Always Dreaming (2017) all managed to complete the Florida Derby-Kentucky Derby double, and Maximum Security (2019) would have done the same if not for his disqualification at Churchill Downs.

Derby contenders based in California: Hot Rod Charlie, Rock Your World, Medina Spirit, Dream Shake, and Get Her Number.

Derby contenders exiting the Curlin Florida Derby Presented by Hill 'n' Dale Farms at Xalapa: Known Agenda (winner) and Soup and Sandwich.

Oppose the Blue Grass and Wood Memorial winners

Two prominent Kentucky Derby prep races — the Grade 2 Toyota Blue Grass Stakes at Keeneland and the Grade 2 Wood Memorial Stakes Presented by Resorts World Casino at Aqueduct — have struggled to produce Derby champions in recent years. No horse has used the Blue Grass as a springboard to success in the run for the roses since Street Sense in 2007, and the last horse to win both races was Strike the Gold in 1991.

The statistics for the Wood Memorial paint a similar picture. The last horse to exit the Wood Memorial and win the Kentucky Derby was Funny Cide in 2003, and the only horse in the past 40 years to win both races was Fusaichi Pegasus in 2000.

Perhaps these trends are nothing more than statistical anomalies overdue to be broken, but a strict interpretation of the historical data suggests the Blue Grass and Wood Memorial tend to rank among the weaker of the major Kentucky Derby prep races. The fact both races were recently downgraded from Grade 1 to Grade 2 status may cement this trend even further, causing top-tier Derby contenders to increasingly target more prestigious races like the Santa Anita Derby and Florida Derby.

Derby contenders exiting the Blue Grass: Essential Quality (winner), Highly Motivated, Hidden Stash, and Keepmeinmind.

Derby contenders exiting the Wood Memorial: Bourbonic (winner) and Dynamic One.

Downgrade horses breaking from post positions #1 and #2

Ferdinand (Four Footed Fotos)

Due to the abnormally large field, the Kentucky Derby can be a challenging race for horses starting from inside post positions. Unless they break quickly, or drop back to rally from behind, it’s difficult for the horses drawn in posts #1 and #2 to secure clean and unencumbered trips.

The rail post is a famously tricky spot and hasn’t produced a Derby winner since Ferdinand in 1986. But post #2 hasn’t seen a winner since Triple Crown winner Affirmed in 1978, suggesting both slots can be bad news. Outside posts are generally preferable, with seven of the last 10 Derby winners starting from post 13 or wider. For much more on Kentucky Derby post positions, check out America’s Best Racing’s Post Positions By the Numbers feature.

Favor last-out winners

Horses who prevailed in their final prep race have dominated recent editions of the Kentucky Derby. If you count the disqualified Maximum Security, the last 10 horses to cross the finish line first at Churchill Downs entered off a victory. Furthermore, eight of those 10 entered the Kentucky Derby undefeated for the season, so it pays to arrive at Churchill Downs in winning form.

Derby contenders who won their final prep race: Essential Quality, Hot Rod Charlie, Super Stock, Like the King, Known Agenda, Rock Your World, Bourbonic, Helium, and King Fury.

Derby contenders undefeated in 2021: Essential Quality, Rock Your World, Helium, and King Fury.

Avoid horses who ran more than three times between January and April

A fresh horse in peak form has the best chance to win the Kentucky Derby, and horses who race too frequently during the winter and spring tend to be at a disadvantage. Between 2005 and 2018, every Kentucky Derby winner competed in just two or three races between January and April of their 3-year-old season.

In 2019, Kentucky Derby winner Country House ran four times during this timeframe, but he was only awarded the roses via the disqualification of Maximum Security, who prepped three times. 2020 Kentucky Derby winner Authentic also ran four times, but this was in response to the postponement of the Derby due to COVID-19, a factor not in play for 2021.

On a related note, it’s also uncommon for Kentucky Derby winners to contest three or more Road to the Kentucky Derby prep races and/or graded stakes between January and April. Since 2007, only Country House and Authentic have won the Derby off such an action-packed racing schedule, and both benefited from the extenuating circumstances outlined above.

Derby contenders who ran four or more races between January and April: Medina Spirit.

Derby contenders who contested three or more Road to the Kentucky Derby prep races and/or graded stakes between January and April: Medina Spirit, Midnight Bourbon, Mandaloun, Caddo River, and Hidden Stash.

Downgrade horses entering off a single start as a 3-year-old

Notwithstanding the above, it’s possible for a horse to enter the Kentucky Derby too fresh and lightly raced. The last horse to crack the Derby trifecta after running just once as a 3-year-old was Challedon, runner-up in 1937.

Derby contenders who have only run once as a 3-year-old: Helium and King Fury.

Beware horses who went unraced as juveniles

Since 1882, only one horse (2018 Triple Crown winner Justify) has won the Kentucky Derby without racing as a 2-year-old. It’s hard to claim the roses without building foundation as a juvenile.

Derby contenders who did not race at age two: Rock Your World, Soup and Sandwich, Sainthood, and Dream Shake.

Long layoffs haven’t been a strategy for success

Since 1956, only two Kentucky Derby winners — Animal Kingdom in 2011 and Authentic in 2020—have won the run for the roses off a layoff of six weeks or more. A strong race within five weeks of the Derby is the usual recipe for success.

Derby contenders entering off layoffs of six weeks or more: Hot Rod Charlie, Midnight Bourbon, Mandaloun, Helium, and O Besos.

Avoid runners who finished off the board in their final prep

In 1957, Iron Liege finished fifth in the Derby Trial Stakes, then rebounded to upset the Kentucky Derby. Remarkably, he remains the most recent Derby winner to finish off the board in his final prep race. All subsequent Derby champions finished fourth or better in their last prep, suggesting horses in poor form a few weeks out from the Derby are unlikely to bounce back in the run for the roses.

Derby contenders who finished off the board in their final prep: Mandaloun and Keepmeinmind.

Upgrade sons of Grade 1-winning routers

Stallions who displayed the ability to win Grade 1 races running one mile or farther have enjoyed the strongest success siring Kentucky Derby winners. Case in point? Ten of the last 12 Derby victors were sired by a Grade 1-winning route runner, with Orb and California Chrome the lone exceptions. If a stallion was an elite-level racehorse running long, there’s a good chance he’ll pass that ability on to his progeny.

Derby contenders not sired by Grade 1-winning route runners: Medina Spirit, Caddo River, Helium, Dream Shake, and Keepmeinmind.


Champion Essential Quality (Eclipse Sportswire)

It’s hard to find a Kentucky Derby contender who perfectly matches the historical profile outlined above, but a couple of horses in the 2021 Derby — Essential Quality and Known Agenda — come very close.

Indeed, Essential Quality qualifies on almost every criterion. He has tactical speed, he finished in less than :38 seconds to win his final prep, he’s undefeated for the season, he’s run twice this year, and he’s a son of the Grade 1-winning route runner Tapit.

Just about the only knock on Essential Quality is the fact he’s exiting the Blue Grass Stakes, which hasn’t been the most productive prep race in recent years. But if you’re willing to forgive this relatively minor shortcoming, Essential Quality looms as a formidable Kentucky Derby favorite.

But Known Agenda appears capable of giving Essential Quality a serious run for the money. He doesn’t have as much tactical speed as the favorite, and he’s not undefeated for the season. But Known Agenda did finish fast when dominating the Florida Derby, his third start of the season. And as a son of 2007 Grade 1 Preakness winner Curlin, Known Agenda certainly has the pedigree to thrive racing 1 1/4 miles on the first Saturday in May.

One high-profile Derby contender who might prove vulnerable at Churchill Downs is Rock Your World, the runaway winner of the Runhappy Santa Anita Derby. While he does match many of the criteria we listed, Rock Your World failed to race as a 2-year-old and finished slowly in the Santa Anita Derby, running the final three-eighths of a mile in just :38.53. History suggests these shortcomings could be stumbling blocks for Rock Your World on Derby day.

Good luck with your handicapping, and enjoy the race!

newsletter sign-up

Stay up-to-date with the best from America's Best Racing!