Time flies when you’re having fun. The Road to the Kentucky Derby Presented by Woodford Reserve is complete and the Grade 1, 1 ¼-mile race itself is less than two weeks away, which means it’s time for handicappers to buckle down and start planning which horses they intend to bet.

Click image to purchase shirt.

There isn’t a horse race anywhere in North America that receives more annual scrutiny than the Kentucky Derby 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 vast troves of historical data? We’ve put together 13 tips and trends to help point you toward the winner of racing’s renowned run for the roses.

Please note: For the purpose of analyzing historically productive betting angles, we are counting Medina Spirit as the winner of the 2021 Kentucky Derby. Although he has been disqualified due to a still-disputed positive drug test, he remains the winner for determining betting payoffs.

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 or near the front end.

Case in point? Between 2014 and 2021, seven out of eight Kentucky 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 gives an edge to late runners. While a fast pace occasionally allows a deep closer to win (Rich Strike in 2022 is a prime example), recent history suggests horses with tactical speed have a substantial advantage in the first jewel of the Triple Crown.

Look for horses capable of finishing strongly

Unbeaten Louisiana Derby winner Kingsbarns (Eclipse Sportswire)

Horses who have shown the ability to finish fast at the end of a 1 1/8-mile or 1 3/16-mile 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 of their final prep race in :38 seconds or less—we’ve compiled a handy chart to help you out.

The data is strong: 19 of the last 25 Kentucky Derby winners successfully shaded the :38 mark in their final prep race, suggesting the ability to finish strongly is important for success on the first Saturday in May.

Derby contenders who finished their final prep in :38 seconds or less: Kingsbarns, Angel of Empire, Two Phil’s, Mandarin Hero, King Russell, Skinner, Tapit Trice, Derma Sotogake, Practical Move, Jace’s Road, Verifying, Major Dude, Reincarnate, Forte, Rocket Can, and Lord Miles. Disarm also came home in under :38 seconds in the Grade 3 Stonestreet Lexington Stakes, but that race took place over 1 1/16 miles, and we project his finishing time would have been slower than :38 seconds over 1 1/8 miles.

Favor California shippers and the Florida Derby winner

Horses based in California have outperformed all others in recent renewals of the Kentucky Derby. Seven of the last 11 horses who crossed the finish line first in the Derby (Medina Spirit, 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 dozen years, 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.

However, the Grade 1 Curlin Florida Derby Presented by Hill 'n' Dale Farms at Xalapa at Gulfstream Park has also been highly productive. Over the last 16 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: Practical Move, Reincarnate, and Skinner.

Derby contenders exiting the Florida Derby: Forte (winner), Mage, and Cyclone Mischief.

Oppose Blue Grass and Wood Memorial Stakes starters, especially winners

Two prominent Kentucky Derby prep races — the Grade 1 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 winners 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 41 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 the Wood Memorial has been 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: Tapit Trice (winner), Verifying, Sun Thunder, and Raise Cain.

Derby contenders exiting the Wood Memorial: Lord Miles (winner) and Hit Show.

Downgrade horses breaking from post positions No. 1 and No. 2

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 post positions Nos. 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-position 2 hasn’t seen a winner since Triple Crown champion Affirmed in 1978, suggesting both slots can be bad news. Outside posts are generally preferable, with eight of the last 12 Derby winners starting from post 13 or wider. Last year, Rich Strike won the Derby from post 20.

Favor last-out winners

Toyota Blue Grass Stakes winner Tapit Trice (Coady Photography)

Horses who won their final prep race have enjoyed an advantage in recent editions of the Kentucky Derby. Nine of the last 12 Kentucky Derby winners entered off a victory, and that number rises to 10 if you count the disqualified Maximum Security. Furthermore, seven of those 12 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: Forte, Practical Move, Angel of Empire, Tapit Trice, Two Phil’s, Lord Miles, Derma Sotogake, Kingsbarns, Confidence Game, and Wild On Ice.

Derby contenders undefeated in 2021: Forte, Practical Move, Tapit Trice, and Kingsbarns.

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 often 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 seasons.

This trend has been broken in two of the last four years by Country House and Medina Spirit, but there’s one caveat to note. Country House ran four times from January through April, but he was only awarded the roses via the disqualification of Maximum Security, who prepped three times.

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

Derby contenders who ran four or more races between January and April: Lord Miles, Sun Thunder, and Cyclone Mischief.

Derby contenders who contested three or more Road to the Kentucky Derby prep races and/or graded stakes between January and April: Angel of Empire, Two Phil’s, Lord Miles, Rocket Can, Sun Thunder, Reincarnate, and Cyclone Mischief.

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 win the roses without building foundation as a juvenile.

Derby contenders who did not race at age 2: Kingsbarns and Mage.

Long layoffs haven’t been a strategy for success

Click image to purchase shirt.

Since 1956, only two Kentucky Derby winners—Animal Kingdom in 2011 and Authentic in 2020—have won the Kentucky Derby off a layoff of six weeks or more. Furthermore, Authentic’s victory came in a Kentucky Derby delayed until September due to COVID-19, which threw off traditional prep schedules.

A strong race within five weeks of the Derby is the usual recipe for success.

Derby contenders entering off layoffs of approximately six weeks or more: Two Phil’s, Derma Sotogake, Kingsbarns, Confidence Game, Wild On Ice, Continuar, Jace’s Road, and Major Dude.

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 an $18.80 upset in the Kentucky Derby. Since then, all but one Kentucky Derby winner has finished fourth or better in their last prep race, suggesting horses in poor form a few weeks out from the Derby are unlikely to bounce back in the most important race of their lives.

The one recent exception to this trend is Mandaloun, who finished sixth in the Louisiana Derby prior to being awarded the 2021 Kentucky Derby victory via the disqualification of Medina Spirit. But as we noted early, Medina Spirit remains the winner for betting purposes, so from that perspective this angle hasn’t missed since Iron Liege in 1957.

Derby contenders who finished off the board in their final prep: Raise Cain.

Upgrade sons of Grade 1-winning routers

Stallions who displayed the ability to win a Grade 1 race over 1 1/16 miles or farther have enjoyed the strongest success siring Kentucky Derby winners. Case in point? Eleven of the last 14 Derby winners (for betting purposes) were sired by stallions who matched that profile, with Orb, California Chrome, and Medina Spirit 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 sired by stallions who won a Grade 1 race at 1 1/16 miles or farther: Forte, Angel of Empire, Tapit Trice, Lord Miles, Kingsbarns, Raise Cain, Rocket Can, Hit Show, Confidence Game, Verifying, Sun Thunder, Mage, Disarm, Reincarnate, Jace’s Road, Skinner, Cyclone Mischief, Major Dude, and Mandarin Hero.

Derby contenders sired by stallions who did not win a Grade 1 racing 1 1/16 miles or farther: Practical Move, Two Phil’s, Derma Sotogake, Wild On Ice, and Continuar.

Avoid betting horses born in January

Since 1983, a span of 40 years, only one horse born in January has won the Kentucky Derby, that being Grindstone back in 1996. February (11 winners) and March (14 winners) have been far more productive months. While this data doesn’t account for the possibility of fewer Thoroughbreds being born in January than February and March, it’s also possible horses born in January are less likely to peak on the first Saturday in May than slightly younger horses.

Derby contenders born in January: Kingsbarns

Beware horses who haven’t raced in North America

The vast majority of Kentucky Derby starters campaign exclusively in the United States and Canada. You have to go back to Bold Forbes in 1976 to find a Kentucky Derby winner who raced elsewhere, starting as a juvenile in Puerto Rico before embarking on a strictly U.S. campaign leading up to the Derby. Since then, horses who have raced outside of the U.S. and Canada have gone 0-for-44 in the Kentucky Derby.

Horses who have raced exclusively outside of the U.S. and Canada have likewise struggled, going 0-for-13 since 1992. None of those 13 managed to finish in the top five.

Derby contenders who have raced outside of the U.S. and Canada: Derma Sotogake, Continuar, and Mandarin Hero.

Derby contenders who have raced exclusively outside of the U.S. and Canada: Derma Sotogake and Continuar.

Conclusions

As of April 24, there are 25 horses under consideration for the 2023 Kentucky Derby. Rooting through the prospective entries, a couple of names stand out from a historical perspective.

The first is probable morning-line favorite Forte, the champion 2-year-old male of 2022 and winner of the ever-productive 2023 Florida Derby. Assuming he can avoid drawing post position one or two, Forte will match nearly every historical trend we’ve outlined. His lone miss comes from a running style perspective; Forte typically rallies from somewhere in the middle of the pack, so he doesn’t have much of the tactical speed that has been so successful in recent editions of the Kentucky Derby.

Runhappy Santa Anita Derby victor Practical Move (Eclipse Sportswire)

The other standout contender is Practical Move, a hard-fought winner of the Santa Anita Derby. He’ll seek to become the eighth California-based Kentucky Derby winner in the last 12 years. While not a pacesetter by any means, Practical Move typically races within two or three lengths of the early lead, so he should have enough tactical speed to sit a favorable trip in the Kentucky Derby. Otherwise, the only knock on Practical Move’s historical profile (assuming he avoids posts one and two) is the fact his sire (Practical Joke) scored his three Grade 1 victories racing seven furlongs to one mile and never nabbed a top-level prize over 1 1/16 miles or farther.

Unsurprisingly, Forte and Practical Move are shaping up as two of the favorites (perhaps the top two favorites) for the Kentucky Derby. If you would rather bet on a longshot, history suggests Skinner is a near-perfect candidate. The stoutly bred son of Curlin raced much wider than Practical Move in the Santa Anita Derby, but nevertheless rallied to finish third by half a length in a deceptively strong performance.

Pending the post-position draw, Skinner has only two issues with his historical profile: he’s a deep closer without any tactical speed, and he failed to win his final prep race before the Kentucky Derby. But if you believe the pace of the 2023 Kentucky Derby will be fast, Skinner is an enticing win candidate who figures to offer dramatically higher odds than Forte and Practical Move. Trainer John Shirreffs has already pulled off one Derby upset with 50.30-1 longshot Giacomo in 2005, and perhaps Skinner can repeat the feat.

Good luck with your handicapping, and enjoy the Kentucky Derby!