The 21st Century Kentucky Derby: Which Horse Wins?

Smarty Jones, Barbaro and American Pharoah (left to right) are three exceptional racehorses that have made history as Kentucky Derby winners this century. (Coady Photograpy/BloodHorse/Eclipse Sportswire)

There is arguably no more storied tradition in American sports than the Kentucky Derby at Churchill Downs. Run for 145 consecutive years, it’s the country’s oldest continuously held major sporting event, and it’s most memorable runnings are etched not only in the history of Thoroughbred racing but in our national memory.

This century has seen 20 Derbys come and go, and the event has only grown in stature and in spectacle. Nine of the top 10 attendance records have come from 2000 through 2019 (including a record 170,513 in 2015), and after a long drought, two horses have won the Derby en route to Triple Crown-winning seasons. The race has been won by all comers over the past 20 years – undefeated heavy favorites, late bloomers, backstretch “wiseguy” types, and proverbial out-of-nowhere longshots.

The ‘fastest two minutes in sports.’ (Eclipse Sportswire)

With this year’s 146th Kentucky Derby Presented by Woodford Reserve postponed to Sept. 5 due to the COVID-19 pandemic, there’s going to be a huge void in the calendar come next Saturday, and the next four months will certainly require a major adjustment of prep races – and even possibly a re-ordering of the Triple Crown series – that will make this year’s run for the roses unique.

But every Derby is unique in its own way, and so are the winning horses. Every horse racing fan has their personal favorites, and will debate at a moment’s notice which Derby winner stood above the rest from its era. Since the 21st century is one-fifth gone, it’s a good time to collect the 20 most recent winners and put them to the argumentative test. Who’s the best Kentucky Derby winner of this century, so far?

For this exercise, I conducted the post-position draw using 20 slips of paper and a Trader Joe’s paper bag, a far cry from the Wednesday extravaganza on site at Churchill Downs (imagine the late, great John Asher drawing this field!).

Weather/track conditions are as follows: sunny, light wind, 72 degrees, fast. (Isn’t that how all Derbys exist in the memory? Aside from the 2018 monsoon?)

Below, behold the 21st Century Kentucky Derby field, presented in post-position order and with morning-line odds, followed by one considered opinion on how the race would all play out (based on each horse’s ability as it stood on Derby day, not on what they accomplished afterward). Alternative scenarios are most definitely encouraged!

1. Barbaro, 2006: If any horse can overcome the dreaded one-hole in the Kentucky Derby, it’s this one. Monstrously talented and game as they come, he outfought a determined foe to win by a half-length in his 1 1/8-mile prep for this race. He’s undefeated, versatile, has expert connections, and has been wowing them on the backstretch all week. A big threat at appealing odds.

Jockey: Edgar Prado; Trainer: Michael Matz; M/L Odds: 10-1

2. Super Saver, 2010: He’s got winning experience over this strip having taken a Grade 2 under the Twin Spires as a juvenile. A consistent type with a home-track jockey, but he’ll have to step up his game big-time to have a shot against this field.

Jockey: Calvin Borel; Trainer: Todd Pletcher: M/L Odds: 30-1

3. Big Brown, 2008: Lightly raced, but he’s toyed with the opposition so far, winning his three starts by a combined 29 lengths. One wonders what will happen when (if?) he’s challenged during a race, but this strapping colt has outrun his pedigree to date and can’t be dismissed. The sponsorship with Louisville-based UPS might drive his odds down, though.

Jockey: Kent Desormeaux; Trainer: Richard Dutrow Jr.; M/L Odds: 10-1

4. I’ll Have Another, 2012: Despite winning two major West Coast Derby preps earlier this year, this runner is flying under the radar – such is the quality of the 21st Century Derby field. He’ll need to work out a stalking trip from near the inside and not get caught in traffic, but this colt will be moving up in the stretch and is a threat to hit the board at high odds.

Jockey: Mario Gutierrez; Trainer: Doug O’Neill; M/L Odds: 20-1

5. Orb, 2013: He transformed over the winter into a legitimate Grade 1 horse for a Hall of Fame trainer who’s yet to win the Derby. This contender is a cut below the top ones in terms of speed figures but should benefit from an honest pace, and has a young but talented jockey known for his closing ability.

Jockey: Joel Rosario; Trainer: Shug McGaughey; M/L Odds: 15-1

6. Fusaichi Pegasus, 2000: Based on the “eye test,” he’s right among the top contenders in a stacked field. There aren’t any apparent gaps in his armor – this $4 million purchase has got the requisite speed figures, an expert trainer, and the ability to rate just off the pace that should serve him well from an ideal post. Watch out.

Jockey: Kent Desormeaux; Trainer: Neil Drysdale; M/L Odds: 8-1

7. War Emblem, 2002: Here’s your pacesetter – this colt has changed up his game in his most recent starts to great benefit by going straight to the front and challenging any horse to catch him, resulting in a pair of dominant wins. Now he’s got a new trainer. Will he be a “rabbit” to set up his more accomplished stablemates?

Jockey: Victor Espinoza; Trainer: Bob Baffert; M/L Odds: 15-1

8. Funny Cide, 2003: This colt has yet to win in three starts as a 3-year-old after excelling as a juvenile against fellow New York-breds, but he’s been competitive in big races, especially his most recent one. He could be rounding into form and is an enticing longshot racing for a fun-loving ownership group of former high school buddies.

Jockey: Jose Santos; Trainer: Barclay Tagg; M/L Odds: 30-1

9. Justify, 2018: The hype is oh-so-strong with this undefeated colt as he attempts to thwart the “curse of Apollo,” and he’s got the right rider to steer him through the toughest field he’s faced to date. He’s a physical specimen who looked like he was just getting to running in his last, a three-length romp at 1 1/8 miles … still, the lack of experience is a concern.

Jockey: Mike Smith; Trainer: Bob Baffert; M/L Odds: 5-1

10. Country House, 2019: He’s a good bet to be the longest shot in the Derby once the gates open, despite showing some improvement in his most recent start when he finished third in a 1 1/8-mile Grade 1. There’s untapped potential here, and he’s trained by one of the best in the business, but it would take something extraordinary (a disqualification, maybe?) to get him to the winner’s circle.

Jockey: Flavien Prat; Trainer: Bill Mott; M/L Odds: 50-1

11. Street Sense, 2007: This champion could be overlooked somewhat by bettors based on his last effort – a close third – but that was on “fake dirt.” Prior to that, he outgamed a talented foe going 1 1/16 miles on the real stuff, and that start, coupled with his dazzling score here last fall, is much more indicative of his true ability. And he’s got a jockey for whom Churchill Downs’ main track is a proverbial home away from home.

Jockey: Calvin Borel; Trainer: Carl Nafzger; M/L Odds: 15-1

12. California Chrome, 2014: Look for these morning-line odds to dip come post time based on fervent fan support but also on ability. It’s well deserved, too – this California-bred deserves a spot among the top contenders in this world-class field. Since being paired up with this jockey, he’s been perfect in four starts, and his admired trainer has prepared him perfectly to handle the Derby’s big stage.

Jockey: Victor Espinoza; Trainer: Art Sherman; M/L Odds: 12-1

13. Animal Kingdom, 2011: Can this talented runner manage the surface switch in the Derby? He emerged on the synthetic last out with an impressive graded stakes score up in northern Kentucky, and has been earning backstretch buzz all week with his training on Churchill’s dirt strip. One thing’s for sure: his rider-trainer combo is as good as it gets.

Jockey: John Velazquez; Trainer: Graham Motion; M/L Odds: 30-1

14. American Pharoah, 2015: Your morning-line favorite is the visual definition of a Thoroughbred racehorse. Conformation, acceleration, cruising speed, agility, mental focus – it’s all there. He has not been challenged in all four of his stakes wins going back to last fall, and has the perfect running style – rating just off the pace – for a crowded field. This is probably the toughest group he’ll ever face, but no other contender has a higher ceiling.

Jockey: Victor Espinoza; Trainer: Bob Baffert; M/L Odds: 9-2

15. Monarchos, 2001: If this colt can regain the form from his eye-catching win in a Grade 1 down in Florida two starts back, he’ll be a solid longshot play in the Derby. He’s shown the ability to rate just off a solid pace and still have something left in the tank. All three of his wins to date have come over the same Sunshine State strip, however, which is a concern.

Jockey: Jorge Chavez; Trainer: John Ward; M/L Odds: 20-1

16. Giacomo, 2005: A solid pace is probable in the 21st Century Derby, which could benefit this stalker/closer. He hasn’t embarrassed himself so far during his 3-year-old season, but he hasn’t won either, and will need everything to fall his way to post a longshot win. He’s the rock ‘n’ rollers’ choice, at least.

Jockey: Mike Smith; Trainer: John Shirreffs; M/L Odds: 50-1

17. Always Dreaming, 2017: This longshot rolls in off of three dominant wins in Florida, but only one of those came in a stakes race. He’s certainly talented but will need to take a big step up against this field. The outside post does him no favors, either.

Jockey: John Velazquez; Trainer: Todd Pletcher; M/L Odds: 20-1

18. Smarty Jones, 2004: This undefeated Pennsylvania-bred takes a back seat to no other horse in terms of back story, and he’s right there among the top tier in terms of talent, too. How his jockey handles the Derby spotlight is a question mark, and he’ll have to hustle out early from the outside to gain a good position just off the pace, but this fan favorite is a major win candidate.

Jockey: Stewart Elliott; Trainer: John Servis; M/L Odds: 6-1

19. Nyquist, 2016: It’s a testament to the quality of this 21st Century Derby field that an undefeated champion could go off as the fourth or fifth favorite. He has taken his A-game from his California base to Kentucky and back, and then down to Florida before arriving at Churchill Downs the picture of consistency. He faces another elite contender right to his inside who prefers the same running style, which should set up an early chess match after the starting gates open.

Jockey: Mario Gutierrez; Trainer: Doug O’Neill; M/L Odds: 8-1

20. Mine That Bird, 2009: The outside post should be of no concern to this come-from-behind runner, a true champion of the little guy who has already made the cross-country trip in a van driven by his New Mexico-based trainer to tangle with the best of his class. Can he shock the world with a new rider who knows this track like the back of his hand? “50 to 1” has a nice ring to it, indeed.

Jockey: Calvin Borel; Trainer: Chip Woolley; M/L Odds: 50-1

The 21st Century Kentucky Derby (presented in footnotes accompanying the ‘official’ race chart):

BARBARO broke sharply, gained a good position on the rail through the first turn, angled out to position three-wide in the backstretch while stalking the pace, methodically moved up into the far turn, swept past JUSTIFY to take a short lead at the quarter pole, dueled with AMERICAN PHAROAH in early stretch before dispatching that foe, was then joined by SMARTY JONES in a thrilling final showdown, narrowly prevailed. SMARTY JONES hustled out early, angled in several paths to position in fifth heading into the first turn, patiently stalked in the backstretch and lost two spots, began picking off horses without asking in the far turn, moved four-wide in early stretch, unleashed a furious rally in the final strides, came up just short. AMERICAN PHARAOH broke cleanly, settled in third behind WAR EMBLEM and BIG BROWN into the first turn, kept in touch with the leaders through the backstretch, moved past that pair at the three-eighths pole while being joined by JUSTIFY and then BARBARO, was called upon by his rider at the top of the stretch and dueled with BARBARO past the eighth pole, yielded late to the winner and runner-up in a game effort. I’LL HAVE ANOTHER beat ORB to an early spot behind pace-pressing BIG BROWN but was taken back several positions through the first turn, stalked in midpack thereafter until angling five-wide in the far turn and commencing a rally, picked off horses from 10th at the top of the stretch to finish well while not threatening the top three. FUSAICHI PEGASUS broke well and established a good position into the first turn, settled in sixth while saving ground in the backstretch, cruised into contention through the far turn to loom just behind BARBARO, AMERICAN PHAROAH, and JUSTIFY, kept to task but lacked acceleration in the stretch while racing four-wide. STREET SENSE avoided early trouble and was taken back, moved to the inside and saved ground thorough the first turn and the backstretch while among the rear guard, began his rally past the three-eighths pole but had to check briefly when JUSTIFY faltered, re-rallied along the rail but could not threaten. CALIFORNIA CHROME broke evenly, secured a spot in midpack through the backstretch while racing four-wide and clear, made a bid entering the far turn to briefly threaten, could not sustain momentum and raced evenly through the stretch. NYQUIST beaten for early position by SMARTY JONES while attempting to angle in after the start, had to check twice entering the first turn while blocked by ALWAYS DREAMING, split the field through the backstretch, made a mild bid through the far turn but could not overcome his troubled trip. JUSTIFY checked out of the gate when WAR EMBLEM angled right causing a mild chain reaction, recovered to establish a prominent spot in fourth behind stablemate AMERICAN PHAROAH, made a bold bid for the lead early through the far turn, held the top spot for a few strides but gave way to BARBARO at the quarter pole and tired thereafter. FUNNY CIDE bumped at the start by WAR EMBLEM and lost any chance at gaining a good early position, settled near the back of the field through the first turn, found a good rhythm through the backstretch and into the far turn, angled six-wide into the homestretch but could not muster a final rally. ANIMAL KINGDOM taken back early, raced evenly through the first mile, angled eight-wide at the quarter pole, picked off tired horses. ORB broke cleanly but was taken back to race amidst a group of horses in midpack, lost several positions through the backstretch, moved five-wide through the far turn, angled out nine-wide at the top of the stretch for a mild rally. BIG BROWN broke well and was positioned behind WAR EMBLEM as the field hit the first turn, pressed that foe through the backstretch and into the far turn, was urged to overtake the leader and briefly did so, but was passed by several horses at the quarter pole and had nothing left for a stretch run. MONARCHOS conceded an early advantage to AMERICAN PHAROAH next to him in the auxiliary gate and raced outside of that foe in fourth through the first turn, lost a position to JUSTIFY in the backstretch, was shuffled back at the three-eighths pole as several other horses moved up, made no impression. GIACOMO had no early speed out of the gate, settled in 18th through the first turn and backstretch, ran evenly through the far turn and moved out seven-wide into the stretch, had no rally. SUPER SAVER was outmaneuvered by BARBARO and BIG BROWN out of the gate, saved ground behind BARBARO through the first turn, moved out and lost several positions through the backstretch, tired after a mile. WAR EMBLEM rushed out of the gate and angled out troubling several horses, corrected course and then moved to the rail with constant pressure from BIG BROWN on his right flank, maintained the lead through solid fractions after a mile, was overtaken at the three-eighths pole and faltered. MINE THAT BIRD held back at the start, moved to the inside to save ground well behind the field and raced off of the TV screen for the first half-mile, started to rally in the far turn while hugging the rail, ran up against STREET SENSE who was paused behind a tiring JUSTIFY, could not regain momentum and faded. ALWAYS DREAMING was aggressively ridden early to secure a spot in seventh while racing four-wide through the first turn, kept that spot through the backstretch, was encouraged by his rider at the three-eighths pole but had no response. COUNTRY HOUSE bothered slightly at the start by WAR EMBLEM’s antics, showed no speed through the stretch and first turn, stayed among the rear guard through the backstretch, no factor.

Margins: nose, 1 ½ lengths, 2 ½ lengths. Final time: 2:00.80 Attendance: 173,069

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