First, a Run for the Roses. Then, a Dash to the Breeding Shed.

VERSAILLES, Ky. — Flightline had put on 100 pounds in the five months since the end of his brief but astonishing racing career. He was still light on his feet, though, as he high-stepped into a breeding shed last month as if he were on a red carpet. A mare named Bernina Star shuffled before him.

Her bloodlines were aristocratic, her racing record impressive. After her career, she fetched $1.2 million at auction to do what she was about to do.

Bernina Star whinnied. Flightline rocked high onto his back legs. The two tangoed and tangled, oblivious to the man holding the mare’s tail or the two other chaperones circling this tryst.

Soon, Flightline’s tail dropped like a flag on a windless day. He fell back to earth. It was time for a bath, and then a night out in the bluegrass.

If the Kentucky Derby is considered the most exciting two minutes in sports, this was perhaps the most lucrative 52.48 seconds in sports. Bernina Star’s owner paid $200,000 for (not quite) a minute of Flightline’s time.

That payday explains why the greatest horses in racing — including, in all likelihood, the winner of Saturday’s Derby — are destined to have short careers, and why fans can’t enjoy the best horses for long. The economics of modern horse racing practically guarantee it.

On the racetrack, it took Flightline two years and six undefeated races to earn $4.5 million in purses. Doing what came naturally twice a day in the breeding shed, he matched that total in 11 days, doubled it in 22 and, with 155 mares in his date book, will have generated $31 million in earnings by the end of the five-month breeding in July.

In a sport perpetually troubled by doping scandals, the frequent and mysterious deaths of its athletes, competition from other kinds of gambling and waning interest among fans, it is a counterintuitive choice to retire him. Just last November, at 4 years old, Flightline was the most exciting thoroughbred in the world. He had won all of his six races by a combined 71 lengths and brought large crowds to see him soar around racetracks like Pegasus.

Imagine LeBron James being pushed into coaching after his second season in the N.B.A. The racing industry has done something like that with Flightline.

“You can work through it and justify it by recognizing that he’s a special talent and you hope he can replicate it and produce fast horses in the future,” said Terry Finley, the founder and president of West Point Thoroughbreds, one of the five entities that owns Flightline.

But Finley conceded that this thinking comes at a cost to fan enthusiasm: “No, it’s not good for the game.”

The Sport of Kings and Diamond Jim Brady

Thoroughbred racing in the United States has a rich and tawdry history that has often mirrored that of the nation. In 1823, Eclipse met Sir Henry in a match race that pitted North versus South, an early window into the regional bitterness that would lead to the Civil War.

The sport has produced folk heroes like Seabiscuit during the Depression, ethereal wonders like Secretariat, the 1973 Triple Crown winner, and Runyonesque gamblers like Pittsburgh Phil and Diamond Jim Brady and modern-day race fixers who got corralled by the feds.

If there is a principle that unifies the sport, it is the inclination — no, commitment — to always take the money.

In Central Kentucky, the money is atop purple-flowered bluegrass that is framed by plank fences and pulled like a canvas over gently rolling hills. Farm roads weave between weather-vaned barns and stately homes. In between are horses as far as you can see.

Foals figuring out the stilts that are their legs. Hungry weanlings trailing after their full-figured mothers. Broad-shouldered stallions languidly patrolling their expansive paddocks like beat cops long after everyone has gone home.

Flightline lives at Lane’s End Farm in a five-acre paddock, a tiny patch of lawn on a 2,000-acre spread.

He takes his turn in the breeding shed with 20 other stallions. Seventy-seven yearlings zigzag in paddocks like the rambunctious adolescents they are. More than 200 mares — some pregnant, others nursing new foals — bring life to this horsy Brigadoon.

Lane’s End and its neighbors are at the center of a $6.5 billion industry that puts 61,000 people to work on more than 831,000 acres. But for how long?

Horse racing has been declining for decades. In 2002, more than $15 billion was bet on races in the United States; last year, the handle fell to $12 billion. In 2000, nearly 33,000 thoroughbred foals were registered, almost double the number from last year.

Still, the competition to create a generational talent like Flightline has never been fiercer.

Breeding to Race or Breeding to Breed?

Horsemen and horsewomen have tried for centuries to breed champion thoroughbreds, relying on a combination of science, intuition and luck. “Breed the best to the best and hope for the best” has been the prayer murmured for generations.

In horse racing’s golden age, the Whitneys, the Vanderbilts and business titans like the textile manufacturer Samuel Riddle bred horses primarily to race. In 1919 and 1920, Riddle’s Man o’ War won 20 of 21 races. When Man o’ War was sent to the breeding barn, Riddle restricted his book to about 25 mares a year, most owned by him or his friends and family.

The 1941 Triple Crown champion, Whirlaway, made 60 starts in his career. The first 11 Triple Crown winners together made 104 starts at age 4 or older, and won 57 of them.

In 1973, one of them, Secretariat, was syndicated for a then-record $6.08 million. He was retired as a 3-year-old after winning 16 of his 21 starts, kick-starting the retail era of breeding.

The last two Triple Crown champions — American Pharoah in 2015 and Justify in 2018 — were also retired at 3, but after running far fewer races than Secretariat. American Pharoah’s stallion rights were bought for $30 million after the colt went 9 of 11 as a 2- and 3-year-old. Justify brought $60 million after only six races, all as a 2-year-old.

Craig Bernick, president of Glen Hill Farm in Ocala, Fla., is from a prominent racing family. He tries to adhere to his grandfather’s model: Breed your mares, keep and race the fillies and sell the colts at auction.

“He was a traditional sportsman,” Bernick said of his grandfather Leonard Lavin, who founded the beauty products company Alberto-Culver, which Unilever bought in 2010. “I wish there were more like him and I could be like that today. But now I must be more commercial. I need to invest in stallion shares and take some of my yearlings to auction in Europe.”

The hurry to get horses to the stallion barn has had unintended consequences in an agribusiness that is contracting: accelerated inbreeding.

While the number of broodmares has remained consistent, the stallion population has dwindled. In 1991, Kentucky had 499 stallions whose books averaged 29.9 mares a year. Last year, Kentucky had 200 registered stallions who averaged 84 mares a year. Many argue that this is not sustainable.

Three years ago, the Jockey Club, which keeps the breed registry, cited scientific studies that showed the thoroughbred gene pool was getting too shallow, endangering the breed. It tried to cap the number of mares a stallion could impregnate at 140. The rule was challenged in court by three farms that collectively stood 16 stallions that bred more than 140 mares each in 2020. One of the farms, Coolmore, also shuttles some of its stallions to Australia to breed another 50 to 100 mares in the Southern Hemisphere.

Last year, the Jockey Club abandoned the rule after the Kentucky legislature, swayed by lobbyists for some commercial breeders, proposed a bill that prohibited the cap and would have put the state racing commission in charge of the registry for Kentucky-bred thoroughbreds.

Bill Farish, the owner of Lane’s End, supported the rule even though the farm stands stallions that breed more than 140 mares.

“It’s just simple math to me,” said Farish, who also has an interest in Flightline. “Maybe my brain works too simply. But if you have half the number of stallions breeding a similar number of mares, it’s got to be shrinking the pool.”

‘We All Know We’re Screwing It Up’

Mike Repole was on the phone. No, make that two phones.

On one, he was barking orders at his bloodstock agent, who was in Ocala, bidding on a filly in a 2-year-old-in-training sale.

“Go to 280 K,” Repole told the agent. “Good.”

Someone bid $290,000.

“Hit them right back,” Repole said, his voice tightening. “Be quicker. Show them we want this one.”

Soon, the gavel dropped at $310,000 and Repole Stable owned another horse.

On the other call, with a reporter, Repole tried to explain the dysfunction of horse racing.

Repole grew up in Middle Village, Queens, and spent ample time on the rail at Aqueduct, the bluest collar of racetracks. He got into the beverage business, building first Vitaminwater and then BodyArmor sports drink into brands attractive enough for Coca-Cola to purchase for nearly $10 billion.

Repole has spent more than $300 million buying horses. He has won dozens of the most prestigious stakes races — including the Belmont on Long Island and the Travers in Saratoga Springs, N.Y. He developed a colt named Uncle Mo into one of the sport’s most accomplished stallions.

On Saturday, he will host 75 family members and friends in Louisville, Ky., at the 149th running of the Derby, where Forte — a colt he co-owns — is the 3-1 favorite.

Repole is confounded by horse racing’s resistance to change and its unwillingness to embrace best practices. For example, if Forte wins the Derby — the first of the Triple Crown races — he will race two weeks later in the second leg, the Preakness in Baltimore. If he doesn’t, he will skip the Preakness to get some rest and return to the track five weeks later at Belmont Park.

“I’m all for tradition, but wouldn’t it be better for the horses if there was more time between races?” he asked. “If the Derby was in May, the Preakness in June and Belmont in July, you would have bigger fields with better horses to get fans excited.”

He has compared horse racing to a poorly run restaurant with a fabulous menu.

“You know the service is bad and you don’t like the room, but once you get there the food is just so good,” Repole said.

He has campaigned for a national league office — a central authority that could bring racetracks, owners, trainers and breeders together on important issues.

“We all know we’re screwing it up,” Repole said. “Horse racing is like a board game with no directions. I’m one of the biggest owners and I don’t know where to go when I have a problem. There is a selfishness built into the game. Everyone treats it like a secret club when we should be sharing and celebrating it.”

In six months or so, Repole and Forte’s co-owner, the Florida Panthers owner Vincent Viola, will decide whether to keep Forte on the racetrack or follow the sport’s unifying principle and take the money by sending him to the barn.

A Comfortable Retirement

For Flightline’s owners, there is no looking back. By the time Flightline’s first offspring hit the racetrack in 2026, he will have generated more than $120 million in revenue.

If they are fast and win races, his stallion fee is likely to rise. America’s leading sire, Into Mischief, is 18 years old and commands $250,000 a mating. If Flightline is unable to consistently pass on his extraordinary speed, his price will be adjusted down.

Either way, if Flightline stays healthy, he will be an equine A.T.M. for the ages.

In Flightline’s racing days, he was so excited to run that his trainer had to take him to the track at 3 a.m. each day so he wouldn’t kick down his stall. Knowing this, the horse’s owners went to great expense to put thick pads in his retirement stall so he wouldn’t hurt himself.

The pads don’t have a mark on them.

Flightline likes what he does — so much so that in the first couple weeks of his new career, he refused to leave the breeding shed long after goodbyes were exchanged.

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