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.

Photos: Rodeo Drive

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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.

******Read the rest of the article here.

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

Here’s the draw for today’s $25,000-added Open finals in the Mercuria NCHA World Series of Cutting at the Houston Livestock Show & Rodeo.

1	THOMAS E HUGHES, 2003 (HIGH BROW CAT x SMART LETHA)
	Horse’s LTE: $334,468 Rider: AUSTIN SHEPARD Owner: KATHY BOONE
2	BOON TOO SUEN, 2005 (PEPTOBOONSMAL x MERADAS LITTLE SUE)
	Horse’s LTE: $126,506 Rider: KOBIE WOOD Owner: GARY ROSENBACH
3	FRECKLED LEO LENA, 2004 (SMART LITTLE LENA x FRECKLED LEO GIRL)
	Horse’s LTE: $73,825 Rider: JAMES DAVISON Owner: FRECKLED LEO LENA
4	JUST PLAYIN SMART, 2000 (FRECKLES PLAYBOY x SMART LITTLE PET)
	Horse’s LTE: $240,450 Rider: MATT GAINES Owner: RALPH GRAY
5	MOCHA CAPPUCCINO, 2003 (ZACK T WOOD x CAPPUCCINO AND PASTA)
	Horse’s LTE: $212,418 Rider: MIKE COLEMAN Owner: LAZY M CATTLE COMPANY
6	I BEN THINKING, 2003 (SOULA JULE STAR x FANCY HANDLE)
	Horse’s LTE: $96,233 Rider: NEIL ROGER Owner: JIMMY KEMP JR
7	CETAS AHOY MATE, 2003 (SMART MATE x CETAS LADY)
	Horse’s LTE: $76,350 Rider: EDDIE BRAXTON Owner: KIRKLAND GRUBER
8	CD APRIL FOOL, 2000 (CD OLENA x ATTRACTIONS FIRST)
	Horse’s LTE: $81,114 Rider: JEREMY BARWICK Owner: FLYING A RANCH
9	GABREYELLA, 2004 (DUAL REY x A PLAYBOYS DESIRE)
	Horse’s LTE: $46,608 Rider: GARY FIELDS Owner: LK CAPITAL ENTERPRISES
10	WOOD YA WANNA, 2000 (ZACK T WOOD x CURLY GRAY HAIR)
	Horse’s LTE: $285,511 Rider: R L CHARTIER Owner: WRIGLEY RANCHES
11	DUAL REY ME, 1999 (DUAL PEP x MISS SMART REY JAY)
	Horse’s LTE: $786,514 Rider: RUSS CARROLL Owner: JEREMY BARWICK
12	WILD HICKORY BOB, 2004 (BOBS HICKORY RIO x PLAYBOYS HONEYGIRL)
	Horse’s LTE: $125,453 Rider: JON WHITE Owner: JUSTIN WHITE
13	VELVETS BEST SHOT, 2003 (PLAYGUN x ENTERPRISE VELVET)
	Horse’s LTE: $24,908 Rider: JAMES PAYNE Owner: MIKE HANCOCK
14	MS PEPPY CAT, 2002 (HIGH BROW CAT x MS PEPPY DOC)
	Horse’s LTE: $183,321 Rider: PETE BRANCH Owner: EL CID LAND & CATTLE
15	SCOOTIN BOON, 2003 (SMART LIL SCOOT x SUSIES BLUE BOON)
	Horse’s LTE: $83,939 Rider: ROY CARTER Owner: S&S FARMS
16	FAITH IN MY CAT, 2003 (HIGH BROW CAT x FAITH IN YOUR MATE)
	Horse’s LTE: $239,804 Rider: TOM LYONS Owner: TOM LYONS