2021 Kentucky Derby tipsheet

The best three-year-old Thoroughbreds in North America have assembled for Saturday’s $3 million Kentucky Derby (G1) at Churchill Downs. The historic 1 1/4-mile prize has drawn a full field of 20, and the top contenders appear evenly matched on paper. A great betting race awaits!

Kentucky Derby pick

• #17 Highly Motivated

Other horses of interest

• #14 Essential Quality
• #1 Known Agenda
• #9 Hot Rod Charlie

Kentucky Derby wagers

• $14 to win on #17 Highly Motivated
• 50-cent trifecta: 17 with 1,9,14 with 1,4,5,6,9,14,15 ($9)
• 50-cent trifecta: 17 with 1,4,5,6,9,14,15 with 1,9,14 ($9)
• $1 trifecta: 1,9,14 with 17 with 1,4,5,6,9,14,15 ($18)

Kentucky Derby contenders

#1 Known Agenda was a flashy winner of the Florida Derby (G1) at Gulfstream Park, where he finished the final three furlongs in :36.59 to earn a 101 Brisnet Speed rating. The son of Curlin is bred to relish running 1 1/4 miles, but he has also raced greenly throughout his career and occasionally refuses to give his best effort. The addition of blinkers has dramatically improved his form and focus, but Known Agenda still drifted sharply toward the rail down the homestretch of the Florida Derby. Part of me wonders if his quirks will become problematic in a 20-horse field.

#2 Like the King has cracked the trifecta in all six of his starts, but his victory in the Jeff Ruby Steaks (G3) came at the expensive of troubled runner-up Sainthood, who ran into traffic issues and might have been the best horse. The fact that all three of Like the King’s victories have come on turf and synthetic is a cause for pause.

#3 Brooklyn Strong beat a good field over a sloppy track in the Remsen (G2) last fall, but an illness prevented him from running again until the April 3 Wood Memorial (G2), where he ran evenly to finish fifth. Brooklyn Strong is more accomplished than your typical Derby longshot, but he is still catching up from the training time he missed during the winter, and the Wood Memorial came back as a slow race on paper.

#4 Keepmeinmind is another who missed training time over the winter, in this case because of poor weather at Oaklawn Park. He never threatened in the Rebel (G2) or the Blue Grass (G2), but his juvenile form was strong, highlighted by a stretch-running win in the Kentucky Jockey Club (G2) at Churchill Downs. Keepmeinmind will drop his blinkers for the Kentucky Derby, which is a hint the plan may be to take back off the pace and make one late rally. I can see this strategy being effective for Keepmeinmind, particularly if he is able to save ground.

#5 Sainthood ran into a world of trouble in the Jeff Ruby Steaks, as he waited in traffic around the final turn, then got bounced around in traffic at the top of the stretch. Despite those obstacles, he rallied to finish second and might have been the best horse. Corey Lanerie is slated to ride in the Kentucky Derby, which sets the stage for a ground-saving trip. Lanerie rode 33-1 longshot Lookin At Lee up the Churchill Downs rail to finish second in the 2017 Kentucky Derby.

#6 O Besos showed steady improvement during the winter, and I loved his third-place effort in the Louisiana Derby (G2), where he sprinted the final three furlongs in :37.29 to rally up the rail and finish just two lengths away from victory. Another ground-saving trip at Churchill Downs can put O Besos in the hunt for a top-four finish, but he may have to fight a few others (mainly Sainthood) to reach the advantageous inside lane.

#7 Mandaloun defeated a good field in the Risen Star (G2) two starts back, but he misfired in the Louisiana Derby, when he faded to finish sixth as the favorite. Some handicappers will draw a line through this effort, especially since Mandaloun has bounced back to train sharply. But Mandaloun lacked an obvious excuse for his disappointing showing, and the last horse to win the Derby after an off-the-board finish in his final prep was Iron Liege in 1957.

#8 Medina Spirit has been busy this season and has cracked the exacta in a quartet of Road to the Kentucky Derby prep races. A wide trip didn’t help his chances when he finished second in the Santa Anita Derby (G1), considering he ran five lengths farther than the winner. But Medina Spirit seems to have flattened out from a Brisnet Speed rating perspective, and others may have more upside for improvement.

#9 Hot Rod Charlie was a sharp winner of the Louisiana Derby and he led most of the way to score by two lengths. He finished the final three furlongs in :37.54 and could be poised for another step forward in his third start of the season. Trainer Doug O’Neill has already utilized this two-prep strategy to garner Kentucky Derby victories with I’ll Have Another (2012) and Nyquist (2016).

#10 Midnight Bourbon has plenty of tactical speed, which he put to good use for a second-place finish in the Louisiana Derby. But the son of Tiznow was losing ground against Hot Rod Charlie and just barely held off O Besos, which marks the sixth time from seven starts that Midnight Bourbon has lost ground from the eighth pole to the finish line. Racing 1 1/4 miles may stretch the limits of his stamina.

#11 Dynamic One arguably pounced too soon in the Wood Memorial, when he took command at the eighth pole and lost by a head against his stretch-running stablemate, Bourbonic. Dynamic One has thrived over 1 1/8 miles and figures to appreciate running a furlong farther in the Kentucky Derby, but the Wood Memorial wasn’t the fastest Derby prep on paper, and the waters will be deeper at Churchill Downs.

#12 Helium showed a lot of grit in the Tampa Bay Derby (G2), when he refused to yield when challenged by Hidden Stash in the homestretch. But the Tampa Bay Derby came back slow from a Brisnet Speed rating perspective, and Helium has only run once this season. The last horse to crack the Kentucky Derby exacta off such an abbreviated prep schedule was 1939 runner-up Challedon.

#13 Hidden Stash put up a good fight against Helium in the Tampa Bay Derby (G2), but couldn’t get by and was losing ground in the final strides. He subsequently finished a distant fourth in a slow-paced renewal of the Blue Grass, where he again lost ground from the eighth pole to the wire. Hidden Stash has ability, but I wonder if 1 1/4 miles might be longer than his best distance.

#14 Essential Quality has been unstoppable, undefeated in five starts, and you have to admire the tenacity he displayed to rally and win the Blue Grass by a neck. The champion two-year-old male of 2020, Essential Quality is versatile in terms of running style, has drawn perfectly, and the son of Tapit is the horse to beat. But several others have posted similar Brisnet Speed ratings, and I wonder whether Essential Quality’s habit of “paddling” with his left front leg will prove problematic and hinder his ability to stretch out over 1 1/4 miles.

#15 Rock Your World won his first two starts on turf, then switched to dirt for the Santa Anita Derby, where he led all the way to score by 4 1/4 lengths, with a 102 Brisnet Speed rating. Rock Your World looms as a dangerous pace player in the Kentucky Derby, but a clean break will be critical for his chances, since Rock Your World has never raced behind horses or experienced dirt kickback. There’s also a possibility he’ll regress in his second start on dirt, as some turf horses switching to the main track are apt to do.

#16 King Fury turned in a visually spectacular performance to dominate the Lexington (G3). The son of Curlin saved ground throughout, rallied powerfully around the far turn, and drew off down the lane to win by 2 3/4 lengths. But a fast pace over a sloppy track gave King Fury a beneficial setup, and there’s no guarantee he’ll receive another ground-saving trip.

#17 Highly Motivated ran too good to lose in the Blue Grass, where he carved out the pace and finished second by neck to Essential Quality. The good news is Highly Motivated ran the final three furlongs in 36.45, and trainer Chad Brown has employed a perfect two-prep approach to bring Highly Motivated to Churchill Downs in career-best form. I don’t think we’ve seen the best Highly Motivated has to offer, so if he settles into a clean trip, behind Rock Your World, he can turn the tables on Essential Quality and win the roses.

#18 Super Stock fired off a career-best effort to win the Arkansas Derby (G1) by daylight, though a fast early/slow late race shape enhanced his rally. Consistency has been a strong suit for Super Stock, who hasn’t missed the board in six consecutive stakes. But Super Stock isn’t the fastest contender on paper, and he’ll have his work cut out to secure a winning trip from post 18.

#19 Soup and Sandwich won his first two starts with ease, then finished second in the Florida Derby, where he was beaten 2 3/4 lengths after he dueled through modest fractions. The big question is whether Soup and Sandwich has enough tactical speed to avoid a wide trip from post 19. His pedigree and form lines suggest the stretch out to 1 1/4 miles is a question mark, and a wide journey wouldn’t help his chances.

#20 Boubonic came flying from far off the pace to upset the Wood Memorial at 72-1. But his Brisnet Speed ratings are a bit light, and he may have benefited from racing over a slow and tiring track in the Wood. The outside post is another obstacle for the stoutly bred son of Bernardini to overcome.