Holland's North American free racing picks for Kentucky Derby Day

Tim Holland provides his expert racing picks across North America along with his picks for the 146th running of the Kentucky Derby.

Churchill Downs

Race 4

Maidens going 6 furlongs include #11 Rye Sense of Humor (6-1), who made progress to finish second in his debut over this distance at Ellis Park last month. Son of Distorted Humor is a half-brother to one winner and is trained by Ian Wilkes, whose runners generally improve in their second outings. Colt posted a solid 4-furlong work in :49 here three days ago and can be along from off the pace with Julien Leparoux remaining aboard.

Race 10: Iroquois (G3)

A competitive field for the Iroquois (G3) includes #8 Midnight Bourbon (6-1), who easily broke his maiden over this distance at Ellis in his second outing. $525,000 2-year-old purchase is a half-brother to Haskell Invitational (G1) winner Girvin, and trainer Steve Asmussen wins at a 22% rate with last-out maiden winners. Bay can be in good position from the start with Gerardo Corrales retaining the mount.

Race 12: Derby City Distaff (G1)

#4 Bell’s the One (10-1) impressed when winning the Winning Colors (G3) over 6 furlongs on this oval two back, and she did not get the best of trips when third in the Madison (G1) over this distance at Keeneland in her latest. Filly is a touch inconsistent, but has run well off short layoffs before and should find a fast pace to close into with Corey Lanerie in the irons.

Race 13: Woodford Reserve Bourbon Turf Classic (G1)

Chad Brown wins with 27% of his runners that have not raced for 46-90 days and saddles #4 Digital Age (6-1), who rallied from off the pace to win an allowance at Saratoga in mid-July. Son of good European sire Invincible Spirit won the American Turf (G2) in his one previous start on this course, and Brown has won with 24% of his starters this year. Colt disappointed in several outings last year, but appears to be back in his best form and gets Javier Castellano in the irons.

Race 14: Kentucky Derby (G1)

#18 Authentic (8-1) can be excused for his lone defeat two back in the Santa Anita Derby (G1). After breaking out at the start, Authentic was forced three-wide while slightly keen on the first turn, but was still able to hold on for second behind Honor A. P., who took advantage of a perfect trip. Most recently in the Haskell Invitational (G1) at Monmouth Park, Authentic was given a slightly overconfident ride on the front end, being only asked late to hold off the charge of Ny Traffic. Son of Into Mischief gets John Velazquez in the irons and may go straight to the lead from a wide post, but he can be in good position if any early speed emerges to his inside.

Saratoga

Race 10: Prioress (G2)

In the Prioress (G2), #7 Center Aisle (4-1) gets blinkers added off a third-place finish in the Victory Ride (G3) at Belmont Park behind two others who return here. Daughter of Into Mischief is out of a half-sister to dual Pacific Classic (G1) winner Skimming and has won one of three starts for trainer Chad Brown, who has prevailed with 21% of his starters at this meet. $1.5 million yearling purchase can be in good position from the start with Joel Rosario remaining aboard.

Del Mar

Race 3

#7 Tapitution (8-1) switches to the main track off an unplaced effort in his June 19 debut racing this distance over the Santa Anita grass. Notably, the second- and third-place finishers both won their next outings. Son of excellent young sire Constitution is out of Summerly, who won the Kentucky Oaks (G1), and trainer Bob Baffert wins with 22% of his second-time starters. Chestnut can show more here under Drayden Van Dyke, who has won with 31% of his rides for Baffert in the past two months.