By KEVIN HELLIKER

KANSAS CITY, Mo.—When he was a titan of Wall Street, Thomas H. Bailey didn’t even know how to mount a horse.

Yet since retiring as chief executive of Janus Capital Group Inc. in 2002, Mr. Bailey has become a rising star in the cowboy sport of cutting.

During a competition here last month, Mr. Bailey and his teammate—a gelding named Kits Lil Pepto—separated, or “cut,” a steer from a small group of cattle, then dashed from side to side to prevent the animal from rejoining its herd. Throughout the wild ride, Mr. Bailey stayed balanced in the saddle, showing why he has earned nearly $90,000 in the sport.

“Tom’s good,” said Matt Gaines, a champion cutter with winnings of $5.7 million, as he watched Mr. Bailey perform.

Mr. Bailey, 73 years old, represents a new force in the corral: the urban cowboy who can’t be laughed off.

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Steve Hebert for The Wall Street Journal

Billionaire Tom Bailey competed in the American Royal Cutting Horse competition at Hale Arena in Kansas City.

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Long mocked as a fake, the would-be Westerner these days isn’t riding mechanical bulls or visiting dude ranches. He’s competing respectably in an Old West sport that measures the ability to handle horses and cows.

Traditionally the pastime of ranch hands, cutting is luring a growing number of urbanites, many of them former captains of finance and industry, who are debunking the notion that real cowboys exist only on the range.

“These business leaders are showing that if they work hard, they can succeed at a cowboy sport,” says Glory Ann Kurtz, a cowgirl journalist who writes a blog called All About Cutting.

Many old timers find all this troubling. A common complaint is that technology has created a super breed of cutting horse so talented that cowboy skills matter less than the money needed to purchase such an animal.

“The average cowboy can’t afford to play no more, horse prices rising so high,” says Pat Jacobs, a 73-year-old Texas rancher and legend of the sport. “Pedigree, I wonder if it hasn’t taken the cowboy almost out of it.”

As evidence that success can be bought, some cowboys point to Jon Winkelried, who last year resigned as the 49-year-old co-president of Goldman Sachs, where he had earned as much as $53 million a year.

A native of suburban New Jersey, Mr. Winkelried early this year made news for adding to his cutting-horse stable a $460,000 stallion named I Sho Spensive. “Winkelried’s 219 Wins Amateur Classic,” a cutting-horse newsletter reported in July, after he nabbed first place in a competition with a score of 219. This year, Mr. Winkelried, who declined to return calls for this story, has more than doubled his total earnings as a rider, to nearly $50,000.

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Write to Kevin Helliker at kevin.helliker@wsj.com