IN THE BEGINNING the Kentucky Derby was easy for Bob Baffert. A wisecracking former quarter horse trainer who made prematurely white hair look cool and rocked sunglasses 24/7 (or so it seemed), Baffert first came to America's most significant race in the spring of 1996 and finished second with a horse named Cavonnier, who lost by a nose. Then he won the next two Derbys, with Silver Charm in '97 and Real Quiet in '98, and each of those horses went on to win the Preakness before narrowly missing the Triple Crown in the Belmont. He got beat with favored Point Given in 2001 but a year later won the Derby again with War Emblem, after persuading one of his clients to buy the horse three weeks before the race. He was 49 and had won three Derbys; only three men in history had won more. "I was like, man, this is gonna be fun to keep coming back," says Baffert.

Baffert is now 62, divorced from his first wife since 2001 and remarried since '02; the four children from his first marriage are in their 20s, and Bode, the 10-year-old son from his second, has never seen his dad raise the Derby trophy. Bob's parents, who were in Kentucky for each of his victories, have both passed away. Three years ago he had a heart attack and required life-saving surgery while preparing for a race in Dubai. It's been a long ride.

This year may be his best chance to return to the winner's circle at Churchill Downs. He holds a pair of aces for Saturday's Run for the Roses, with likely favorite American Pharoah and unbeaten Dortmund, who could be the second betting choice. In the 13 years since his last Derby win Baffert has started 12 horses. He lost with Pioneerof the Nile in '09 because Calvin Borel got a crazy-fast rail ride on 50--1 long shot Mine That Bird. He lost in '10 because Lookin At Lucky got trapped inside after drawing the deadly No. 1 post position. He lost in '12 because Bodemeister got nailed in the final strides by I'll Have Another after having led the field for nearly all of the race's 1¼ miles. He also started half a dozen horses with no chance—"The worst feeling," he says—and there were four times he didn't have a starter. All of this, he says, is "humbling," an ongoing lesson in the harsh realities of asking a 3-year-old horse to run farther than it has ever run before.

Dortmund, a giant chestnut by '08 Derby winner Big Brown, is unbeaten in six races and swept the major West Coast Derby preps. American Pharoah, a bay son of Pioneerof the Nile, has won four straight and took the Rebel Stakes and the Arkansas Derby at Oaklawn Park by a combined 14¼ lengths. Dortmund is powerful; American Pharoah is smooth and quick. Both colts will face what is regarded as one of the deepest Derby fields in years. "I've won it, and I've seen so many disappointments," says Baffert. "My horses are good, but they've got to break [from the gate], get some racing luck and have a good trip. There's a lot of anxiety right now. But it's a good anxiety."

THREE OTHERS TO WATCH

MATERIALITY

Trainer:

Todd Pletcher

The son of Afleet Alex is unbeaten this year, but didn't race in 2014. No horse who was unraced as a 2-year-old has won the Derby since 1882.

CARPE DIEM

Trainer:

Todd Pletcher

The winner of two Derby preps was bought for $1.6 million as a 2-year-old, making him the most expensive horse in the race.

FROSTED

Trainer:

Kiaran McLaughlin

The winner of the Wood Memorial often races in traffic and has finished second four times in seven lifetime starts.

PHOTODANNY JOHNSTON/AP (AMERICAN PHAROAH)Front Runners Baffert (inset) primed American Pharoah to win the Arkansas Derby (top). PHOTOANDY LYONS/GETTY IMAGES (BAFFERT)[See caption above] PHOTOMATTHEW STOCKMAN/GETTY IMAGES (MATERIALITY)

HOLE YARDS PAR R1 R2 R3 R4
OUT
HOLE YARDS PAR R1 R2 R3 R4
IN
Eagle (-2)
Birdie (-1)
Bogey (+1)
Double Bogey (+2)