James Cheng / MSNBC.com

"Cowboy" Jack Kaenel poses for a photograph at Emerald Downs in Auburn, Wash., on Tuesday. This is the 25-year anniversary of Kaenel's Preakness Stakes victory, when at the age of 16 he became the youngest jockey ever to win the race.

So Kaenel was by no means inexperienced when he rode Aloma’s Ruler in the Preakness less than 10 months later, picking up the mount after Hall of Fame rider Angel Cordero Jr. elected to ride a different horse in the final prep for the Preakness, the Withers Stakes.

The race unfolded the way trainer John “Butch” Lenzini Jr. had planned, and Kaenel executed the game plan perfectly. He sent Aloma’s Ruler to the front out of the gate, then slowed down when no one pressured him.

Rounding the far turn, Shoemaker, 50, moved Linkage up to challenge Aloma’s Ruler and the rider who could still go a week between shaves.

But Kaenel had saved plenty of horse, and Shoemaker was unable to get Linkage closer than the half-length final margin.

Said Shoe: “My horse ran great, but his horse did too. ... We did the best we could.”

Dan Farley of the Thoroughbred Record wrote that Kaenel was “the story to come out of the 107th Preakness.”

“Kaenel has, through his family’s somewhat nomadic life (they still pull around the same old trailer they had when Jack was a kid) grown to be a self-assured, somewhat cocky but likeable young man. When one considers what the life of a racetracker has done to some, Kaenel has come out quite well indeed, thank you.”

Kaenel continued to ride on racing’s A circuit for the next few years and married Crough in 1984.

Not long afterward, he began traveling among racing circuits with a growing family and other kin and hangers-on.

Warren, the former jockey, recalls being at Santa Anita in 1985 or '86, when the Kaenel entourage pulled into the parking lot.

“He drove in with a trailer and a bunch of donkeys and all kinds of stuff,” he said. “It looked like a traveling circus.”

Golden Gates Field Jack Kaenel rides Brown Bess to victory in the 1989 Yerba Buena Handicap at Golden Gate on May 13, 1989. Brown Bess was an Eclipse Award winning turf mare, one of Kaenel's last great mounts.

Crough said Kaenel’s drinking grew steadily worse during the gypsy years and when the family made Northern California their base in the late 1980s. By the mid-1990s, she said she had had enough.

“He said, ‘Give me one more chance. It’s being around this fast-paced life. I’ll retire and we’ll move back to Kansas and I’ll be able to stop drinking that way,’” she said.

“The retirement lasted three months when he decided he wanted to go back to riding, which meant he wanted to go back to drinking. That was probably the death of our marriage right there.”

The couple divorced in 1997.

By that time Kaenel was missing races without any excuse and going through periods where he would quit riding entirely and his weight would soar to 150 pounds — far above his riding weight of 117. And even when he was showing up, trainers and owners were reluctant to give him mounts because of his increasing unreliability.

Kaenel had one more moment of glory in 2003, when he rode the racing mule Taz in a series of highly touted races.

But two months later, the California Horse Racing Board revoked his license after he was discovered to be drunk while exercising horses in Sacramento. It was reinstated the following year, on the condition that he abstain from alcohol, but again revoked in June 2006 after racing authorities in another state reported that he had been found inebriated.

Kaenel doesn’t relish talking about the impact his drinking has had on his career, but he acknowledges that it “definitely didn’t help at all.”

He says he has been sober for “a few months now,” and is feeling healthier than he has in years. He is considering a comeback if authorities grant him a jockey’s license so he can race at Emerald Downs near Seattle.

His recent health scare has given him additional impetus to get back to riding.

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