by Craig Pittman | October 14, 2020

Meet the Godfather of Greyhound Racing

The Winning family is greyhound racing royalty, but this year their 100-year reign comes to an end, along with the entire sport.

Derby Lane has been heralded as the “Churchill Downs of greyhound racing.” Photography by Mary Beth Koeth.

As the race began, the eight sleek dogs exploded from the starter’s box, their paws throwing showers of sand behind them as they hurtled down the first straightaway on the oval track. In seconds, they had reached 45 mph. 

From his third-floor office window at Derby Lane, Richard Winning can look down and see the dogs running. The greyhound racetrack near St. Petersburg’s waterfront has been owned by his family since it opened in 1925. Sportswriter Ring Lardner once hailed it as “the Churchill Downs of greyhound racing.”

Winning can see the grandstands that were once filled with thousands of screaming fans and now hold only a few hundred. He can remember when the regular customers included baseball great Stan Musial and mob boss Santo Trafficante Jr., and a live band played between races. He can still taste the 37-ounce prime rib once served at the track’s restaurant.

He can also see the end, coming up fast.

Five years ago, when Winning took over as CEO of the company that runs Derby Lane, the St. Petersburg Kennel Club, he knew that the dog track was headed for a crisis. The company’s take from people betting on the dogs had been in decline since the late 1980s. By 1999, Derby Lane’s treasurer told Harper’s magazine that Winning’s family could make a bigger profit by simply selling the land and investing the money.

Derby Lane CEO Richard Winning has worked every job at the track besides playing in the band. Photography by Mary Beth Koeth.

But Winning didn’t realize when he got the job that he’d be presiding over the shutdown of the oldest continuously operated dog track in America. 

Voters repulsed by TV ads depicting repeated injuries among the racing dogs decreed two years ago that all of Florida’s greyhound tracks must discontinue racing by Dec. 31, 2020. At the time, Florida held more dog tracks than any other state—11 out of the 17 nationwide. Ending greyhound racing in the Sunshine State will likely put pressure on the few remaining tracks around the nation to close as well.

Video: Florida says goodbye to greyhound racing

“It’s a shame to have to shut down after 95 years,” said the gray-bearded Winning, 64, slumped back in his desk chair, a trio of cigars peeking from the pocket of his teal fishing shirt. He figures he’ll be OK, but he’s worried about Derby Lane’s legacy.

“In 20 years,” he said, “will anyone even remember what greyhound racing was?”


The dogs flew around the track, chasing a white rabbit known as “Harrison Hare,” its mechanism whirring along a rail emitting a series of loud metallic squeaks and shooting out blue sparks.

Horse racing is known as the “sport of kings.” Greyhound racing calls itself the “sport of queens,” because Queen Elizabeth I was a huge fan of a sport called coursing, in which two greyhounds would be released to chase a live hare. The winner caught and devoured their quarry.

Greyhound racing as we know it today began with Owen P. Smith, the son of a Memphis undertaker, who thought that coursing was too brutal. To him the dying rabbit sounded like a child screaming. He tinkered with various designs until, in 1910, he secured a patent for what he called the “Inanimate Hare Conveyor.” 

What was once the sport of queens became the sport of blue-collar bettors when lights were added and the dogs could race at night. Photography by Mary Beth Koeth.

In addition to inventing the mechanical rabbit track, Smith and a partner opened the first oval dog track in a town near Oakland, Calif., in 1919. It failed, as did several others they opened in other cities. They failed in part because Smith would not allow betting on the races. After all, betting was illegal.

But then, in 1922, he and some partners opened a track in a South Florida town then known as Humbuggus, later renamed Hialeah. It was so close to the Everglades that the track had to hire someone to catch the snakes that tried to slither in. Despite that, the Hialeah track became the first commercially successful dog track in the U.S., thanks in large part to the addition of electric lights so the greyhounds could run at night.

Rather than the sport of queens, the lights turned greyhound racing into the sport of the blue-collar bettors. Working people with day jobs could now enjoy the show each night. Five thousand people turned out for the first race, watching a dog named Old Rosebud take the $60 purse, according to an article by Michael LaPointe in The Paris Review. (The “Great Miami Hurricane” demolished the track four years later, and new owners converted it to the horse track that it is today.)

Derby Lane, the first track not affiliated with Smith, opened under a cloud in January 1925. The partners who built it ran out of money before they could hold the first race. They couldn’t pay St. Petersburg businessman T.L. Weaver what they owed him for either the land they had bought from the real estate magnate or the lumber he’d sold them to build the grandstands.

That’s how Weaver, Winning’s great-grandfather, wound up taking over a racing venue in which he had no initial interest. He rounded up some partners to help finance its operation, Winning said, but nobody knew anything about dog tracks then. “They were like, ‘What do we do?’”

The track operated only in the cooler months, and in the summer off-season Weaver grew beans in the infield. He sometimes opened the track for nonracing events, such as an exhibition football game featuring Jim Thorpe, according to track historian Louise Weaver, who is Winning’s second cousin.

Derby Lane also played host to other stunts, such as a race in which monkeys in uniform rode the greyhounds. The monkeys’ uniforms were stitched to the racing blankets that the dogs wore, so they couldn’t jump off, Weaver said.

The winning monkey earned a trophy full of peanuts. Photography by Mary Beth Koeth.

“Nobody was happy about that, and I’m not talking about the people,” she said.

Derby Lane didn’t really need such stunts to succeed. Following Hialeah’s lead, it installed electric lights for nighttime racing and thus drew working stiffs as well as celebrity fans. The track’s location turned out to be ideal for attracting customers, too. The first bridge across Tampa Bay had just opened near Derby Lane, meaning spectators could easily drive over from Tampa to see the dogs run. Prohibition was in full swing, so a speakeasy had opened on nearby Weedon Island, offering drinks and dancing and the occasional shoot-out among competing bootleggers. Both the speakeasy and the track became a draw for ball players like Babe Ruth, visiting for spring training.

Who’s going to stop the Babe?
— Richard Winning

“My great-grandfather used to go golfing with Babe Ruth,” says Winning, a skilled raconteur with a vast storehouse of entertaining yarns. Their golfing group would go to a country club in Tampa to play, despite the fact that none of them were members, he said. They got away with trespassing, he explained, “because who’s going to stop the Babe?”


The bettors in the stands watched the eight dogs thunder around the turn, headed for the back stretch. Many sat at tables covered in little white betting slips, a sign of how many times they’d lost.

Despite being illegal, gambling at dog tracks ran rampant in the 1920s. To get around the law, “they did something sneaky,” Winning said. “They sold shares in the dogs.” 

Winners would get their money back plus a “dividend.” Losers would fail to recoup their “investment.” Other tracks skipped the subterfuge and ran “on the fix”—in other words, they bribed local lawmen.

But by the end of the 1920s, Florida’s local governments were desperate for money.  Prohibition had ended income from liquor taxes, and the Depression wiped out income from property and gas taxes, said historian Gary Mormino. Florida had already banned the income tax to try to attract rich people to the state. State legislators wondered: Why not legalize what was already happening, then tax that?

Before betting on horse and dog races was legal, bribery and loopholes allowed people to gamble under the table. Photography by Mary Beth Koeth.

In 1931, Florida legislators passed a bill to legalize and tax betting on horse and dog races, then share the tax revenue with all 67 counties, regardless of whether they had tracks or not. The prospect of getting equal shares persuaded enough of the anti-gambling legislators to vote for the measure, Mormino said.         

Then-Gov. Doyle Carlton, a Bible-thumping Baptist, opposed the bill and later complained that it passed only because “interested parties were buying their way through the legislature.” Carlton said pro-gambling forces offered him a $100,000 bribe to sign the bill into law. He vetoed it instead—but state senators overrode the veto, making Florida the first state to legalize betting on horse and dog races.

Once betting was legal, dog racing’s popularity in Florida soared. New tracks opened around the state and the originals, like Derby Lane, saw a surge in customers. The image of racing greyhounds became an element of Florida’s carefree vacationland image, part and parcel of the palm trees and sandy beaches. Racing greyhounds even showed up in the opening credits of Miami Vice. 

In her vast collection of Derby Lane memorabilia, which includes everything from bobblehead greyhounds to retired versions of the stiff-legged Harrison Hare, historian Weaver keeps black-and-white photos of the old days. They show people thronging the grandstands in suits and ties and hats, as if they were attending Sunday church services. 

Along with the blue-collar bettors, greyhound racing also attracted big celebrities like Joe DiMaggio and Mickey Mantle. Photography by Mary Beth Koeth.

Winning recalls gamblers with nicknames like Champagne Tony, Dropsy and the Flicker hobnobbing with celebrities and sports figures at Derby Lane. Florida novelist Tim Dorsey used Derby Lane’s colorful customers as inspiration for the names of characters in his wacky crime novels, according to the track CEO.

“Mickey Mantle made a cigarette commercial here,” Winning said. And at one point, he said, Joe DiMaggio left Marilyn Monroe in a car with the motor running, chatting with the parking valet while he ran inside to place his bets. 

Weaver says Joltin’ Joe even paid the valet for spending time with the most famous movie star in the world, but the valet would have done it for free.

In Winning’s office, the CEO keeps a large painting of St. Louis Cardinals great Musial because, he said, he once dated one of Stan the Man’s daughters. It’s one of several might-have-beens in his life.


The dogs are on the backstretch now, jockeying for position. They’re going so fast, the numbers on their colorful fitted vests known as “blankets,” are just a blur. One dog takes the lead, a second close behind, while another falls behind the pack.

Over the years, ownership of the track passed from family member to family member like a Biblical countdown of “begats.” T.L. Weaver handed off the CEO job to his son-in-law, John Brooks, who had married the oldest of his six children. Brooks then passed it to Arthur Vey Weaver Sr., who handed it over to Otto Weaver, who passed it along to A.D. Weaver and so on.

Richard Winning never intended to join the family business, but the adrenaline proved to be too strong of a pull. Photography by Mary Beth Koeth.

Not everyone in the family worked at the dog track. Winning’s father Dick Winning owned Chrysler-Plymouth auto dealerships in St. Petersburg, Seminole and Fort Myers. As a young man, Richard Winning worked there in the parts department, the body shop and the wash rack before heading off to Staunton Military Academy in Virginia. Then he came home, got a degree from St. Petersburg Junior College and started taking classes at the University of South Florida.

After more than a year at USF, Winning was supposed to head down to Haiti, where his father was part owner of a watchband factory that had contracts with Timex and Bulova.

“I was going to go down there to run the plant,” he recalled. 

But before it was time for his departure, he needed money. In 1975, he took a part-time job collecting 50-cent pieces from the turnstiles at Derby Lane. When the time came for him to leave for Haiti, he never got around to catching that plane. The excitement of the track had gotten in his blood. 

Over the next 45 years, he said, “I worked everything out here at the track, except playing in the band.” The experience showed him “how it all fits together.” In the meantime, he married and had three children—one of whom, Alexis, 37, now serves as Derby Lane’s public relations coordinator.

I worked everything out here at the track, except playing in the band.
— Richard Winning

The track consumed his life. He grew accustomed to working from 9 a.m. to 4:30 p.m., going home for a bite to eat, then coming back to Derby Lane about 7 p.m. and staying until the track closed. He joked that he followed this schedule “nine days a week.”

As Winning climbed toward the job of CEO, the greyhound racing industry was hitting its peak. In the 1980s, attendance and revenue soared. Everyone assumed the industry would keep growing like that forever.

But racing had benefited from having little competition for entertainment and gambling dollars. That was about to change. 

“Go back to 1987, which was our peak year with $105 million (wagered),” Winning said in a 2015 interview with the Tampa Bay Times. “We were open four months out of the year, and we would run 1 million people through our turnstiles. Today, it takes us about all year to get 600,000 people, and our handle is nowhere near that.”

Thanks to the rise of other gambling options, greyhound racing has seen a significant downturn in attendance. Photography by Mary Beth Koeth.

One of Winning’s jobs at Derby Lane was serving as the track’s lobbyist in Tallahassee, so he had a front-row seat when the Legislature approved the creation of a statewide lottery to fund education. Meanwhile, the Seminole Tribe opened a bingo hall in Hollywood and established that Native American tribes had a legal right to open casinos. Between the lottery and the casino slot machines, bettors now had far more choices for spending their money, and dog tracks started seeing a drop in revenue.

By 2004, the Seminoles had opened a casino in Tampa, too. That casino “is doing a tremendous amount of business, and our customers are driving by us to go there because we don’t offer what they want to do,” Winning said in 2015. By comparison, he said, “We’re in the buggy whip industry.”

To fight back, Winning and other racing industry lobbyists persuaded the Legislature to let them open card rooms for penny-ante poker, as well as full-card simulcasting, which allows bettors at one venue to wager on races at another. But it wasn’t enough to turn things around for the dog racing industry.

The fans who remained loyal tended to be older. By 2001, when Steven Soderbergh filmed a scene at Derby Lane of Brad Pitt recruiting someone for the Ocean’s Eleven band of thieves, the crook in question was played by Carl Reiner, then 79. He fit in perfectly with the gray-haired Derby Lane clientele.

“Young people don’t like to have to handicap the dogs’ chances,” Winning grumbled. “They just want to stare at their phones.”


The dogs thunder down the final stretch. Two of them are neck and neck, leaving the other six behind. As the pair blaze across the finish line, they set off a camera that snaps a photo showing one of them winning by a nose.

When Winning thinks back about the dogs he’s seen compete at Derby Lane, one name jumps out: a champ called Keefer. So many people turned out in 1986 to see Keefer win the Distance Classic, the record for the largest crowd in track history was set: 12,779 people. That was a year after Keefer got tangled with other dogs in a race and suffered a hairline fracture in one leg. The dog recovered and bounced back.

“Keefer’s the only greyhound I know of who made the front page of the Wall Street Journal,” Winning said. “He was a hell of a dog to watch run.”

Opponents of dog racing often point to the number of greyhounds that suffer injuries during their racing days—fractured legs, spinal injuries, sometimes something worse. Winning compares them to professional athletes. Football players get injured constantly, but nobody’s calling for shutting down the NFL, he said.

Greyhounds often suffer serious injuries from racing, like fractured legs and spinal injuries. Photography by Mary Beth Constante.

What’s hard to argue with, though, is what happens to the ones that fall short of placing one too many times. In 2002, a security guard for a track in Pensacola was arrested after authorities found a junkyard in Alabama where, over a period of 10 years, he had killed and buried between 1,000 and 3,000 greyhounds that could no longer race. Although he said he’d been paid $10 by the kennels for each bullet he put in the dogs’ heads, some of them had been shot in the neck or face, meaning they suffered before they died. A prosecutor called it a “Dachau for dogs.” 

Eight years later, at a track in the Panhandle town of Ebro, the Washington County Sheriff’s Office charged a trainer with 37 counts of animal cruelty after finding only four dogs left alive of the 37 he’d had a month earlier, when the racing season ended. The rest had starved to death. Complaints about the stench had led a state official to discover the gruesome scene.

We saw this coming for years. Activists have been attacking it, and dog racing was easy pickings.
— Richard Winning

Such reports fueled the efforts of Grey2K to push for a ban on greyhound racing in Florida. The organization failed for 10 years to persuade the Legislature to pass such a bill, but it succeeded in getting the Constitution Revision Commission to put the question to the voters in 2018 as a constitutional amendment. 

Track owners like Winning, and kennel owners and dog trainers too, bet on Amendment 13 failing. But their opponents raised more money—$3 million, compared to $500,000—and ran far more TV ads. The Grey2K ads focused on reports of dogs being injured and treated inhumanely, while the racing industry’s ads tried to argue that banning greyhound racing would somehow ban hunting in Florida too.

Richard Winning didn’t expect Florida voters to ban greyhound racing. Photography by Mary Beth Koeth.

The end result was no photo finish. Nearly 70 percent of the voters backed Amendment 13, calling for the end of greyhound racing by the last day of 2020. Winning lost.

He admits to being surprised and suggests it was all a big mistake: “It was at the bottom of a list of very confusing amendments. I don’t think people understood what they were voting for,” he said in a 2018 interview with the Business Observer. The excuse sounds hollow when compared to the measure’s huge margin of victory.

Winning conceded that greyhound racing has been headed for the final stretch for a long time: “We saw this coming for years. Activists have been attacking it, and dog racing was easy pickings. They’ve also been targeting Sea World, going after the zoo; they got rid of the circus. Next, they’ll go after hunting dogs; they’ll go after everything.”

In a more recent interview with this reporter, he also blamed the state of Florida for not assisting the industry that has shared so much of its profits with the government since 1931.

“This industry has given hundreds of millions of dollars to the state of Florida over the years,” he said, “but as it dropped off, the state failed to come help us stay alive.”


The race is over. The successful bettors go collect whatever they’ve won, while the losers drop their tickets on the floor or in the trash. Meanwhile, the panting dogs mill around until the young employees known as “lead outs” walk up and snap leashes to their collars. The lead outs escort the eight greyhounds back to their kennels for some water and a quick dip in a trough to cool down. They’re done.

Amendment 13 says all the dog tracks must shut down by Dec. 31. The last day at Derby Lane will be Dec. 27, a Sunday. Many of the track’s 400 employees will be out of work. But not Winning.

In 20 years, will anyone even remember what greyhound racing was?
— Richard Winning

Although greyhound racing will end, Derby Lane’s poker room and simulcasting will continue, he said. It’s a way of adapting. Winning said he is unsure what will happen to the real estate where the track now stands. Some people have talked about tearing down the track and grandstands to convert them into a bigger, better stadium for the Tampa Bay Rays, but so far no one has made a formal proposal, he said. He’s not sure it’s such a great spot for a stadium, given what the rising sea level has done to storm surge maps.

In the meantime, the track is reaping some profit from its emptiness by renting out much of its parking lot to Amazon. Hundreds of the online giant’s gray delivery trucks park there overnight, and in the daytime the company uses part of the paved area to train new drivers. That, too, will continue, Winning said.

The fate of Derby Lane’s track is murky, but by the end of 2020, it will no longer host any greyhound races. Photography by Mary Beth Koeth.

As for the 776 dogs still racing at Derby Lane, the trainers who want to keep racing will load up theirs and drive to one of the two states where greyhound racing remains active and legal, Iowa and West Virginia.  The rest will depend on greyhound adoption agencies to find them new homes. Those groups are scrambling to arrange for them to be taken by caring families before the year is out. So far, they say, a lot of adopters are lining up to take them because greyhounds have a generally good reputation as pets.

Throughout Winning’s career at Derby Lane, he and the cousin who preceded him as CEO had a frequent saying they used whenever facing any challenge. It became their mantra, their reassurance that success would follow every endeavor: “Things will happen the way they’re supposed to—you just gotta believe.” 

These days, though, he’s not so sure.

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CRAIG PITTMAN is a native Floridian and award-winning journalist. He spent 30 years at the Tampa Bay Times and now writes a weekly environmental column for the Florida Phoenix. He is the author of five books, including the New York Timesbestseller Oh, Florida! How America’s Weirdest State Influences the Rest of the Country, which won a gold medal from the Florida Book Awards. His latest, published in January, is Cat Tale: The Wild, Weird Battle to Save the Florida Panther. The Florida Heritage Book Festival named him a Florida Literary Legend, and he just started a podcast called “Welcome to Florida.” He lives in St. Petersburg with his wife and children. Click here to read his feature story about the ladies of the Glades from our Summer 2020 issue.