In the Kentucky Derby, the trip, not the post, is of more importance. Break badly, get hung wide or get banged around in the crucial run to the first turn, and it's all but over. On Saturday, Big Brown must avoid those problems while breaking from the extreme outside.

Big Brown had to overcome the far outside post 12 when he won the Florida Derby five weeks ago at Gulfstream Park. Now at Churchill Downs, when he tries to become the first horse in 93 years to win the Kentucky Derby off just three starts, Big Brown will be farther out, as far as can be, in post 20, the position co-owner Michael Iavarone and trainer Richard Dutrow Jr. surprisingly selected when post positions were set on Wednesday night for the 20 runners entered in the 134th Derby.

Big Brown, who has won his three starts by a combined 29 lengths, was installed as the 3-1 favourite on the morning line set by Mike Battaglia of Churchill Downs. Mike Watchmaker, Daily Racing Form's national handicapper, also has Big Brown at 3-1.

However, the last Kentucky Derby winner with just three career starts was filly Regret in 1915. The last winner with fewer than five was Exterminator in 1918.

Big Brown may lack experience, but jockey Kent Desormeaux does not. He won the Derby in 1998 with Real Quiet and again in 2000 with Fusaichi Pegasus.

Colonel John wound up in post 10 and will be ridden by Corey Nakatani. He is the second choice of both Battaglia (4-1) and Watchmaker (5-1). The top 3-year-old on the West Coast, Colonel John arrived in Kentucky off a victory in the Santa Anita Derby on April 5. He has four wins and two seconds in six career starts for trainer Eoin Harty.

However, Colonel John has never raced on dirt before, but only on synthetic tracks. He showed a liking for the dirt with a blistering workout this week.

Pyro, who won the Louisiana Derby before finishing 10th in the Blue Grass Stakes, is the third choice on both lines at 6-1. He landed post 9. Trained by Steve Asmussen, Pyro will have Shaun Bridgmohan aboard. Asmussen also has another entry in Z Fortune, who enters off a second-place showing in the Arkansas Derby.

Eight Belles wound up with post 5. She is 30-1 on Watchmaker's line. The Larry Jones-trained filly becomes the first filly to run in the Kentucky Derby since 1999, when Excellent Meeting finished fifth and Three Rings was 19th. Three fillies have won the Derby, most recently Winning Colors in 1988.

This marked the fifth straight year that the Derby had the maximum of 20 horses entered in the race. In fact, 24 were put in the entry box on Wednesday morning. But the field is capped at 20, based on earnings in graded stakes races, so Halo Najib, Tomcito, El Gato Malo, and Kentucky Bear were denied spots. There is no also-eligible list for the Derby, so none of those four horses can move into the race if any of the 20 in the field subsequently scratches.

The lottery gave Visionaire's connections the first pick (he's in post 8) and the last one to Gayego (post 19) in the afternoon's Derby draw.

Undefeated Big Brown went 16th, and with posts 1, 2, 18, 19 and 20 remaining, co-owner Michael Iavarone chose No. 20. The far outside is generally considered a poor spot because runners drawn there often lose ground if horses with similar styles bunch up inside them during the run to the first turn. Many of the horses considered front-runners in this Derby, including Big Brown, are grouped together near the outside.

With 20 runners, the Derby's overall purse will be $2,211,800, with $1,451,800 - and a garland of roses - going to the winner.

Source: NTRA, Racing Post and others