1. Florida

Mary Margaret Winning passed out trophies at Derby Lane, but she won them for herself away from the track

In St. Petersburg, she stayed busy and made her mark on society.
Derby Lane opened about a month after Mary Margaret Winning was born. She’s pictured here in 1933 giving a trophy filled with nuts to the monkey jockey who won the race. (Photo courtesy Alexis Winning)
Derby Lane opened about a month after Mary Margaret Winning was born. She’s pictured here in 1933 giving a trophy filled with nuts to the monkey jockey who won the race. (Photo courtesy Alexis Winning)
Published Aug. 6, 2019
Updated Aug. 6, 2019

Mary Margaret Winning sat near the engine of the boat bobbing in the waters of Boca Grande, watching. She was neatly dressed, as always, her short blonde hair set in the arcing curls she’d worn for years.

Nearby, her oldest granddaughter was worn out after catching and reeling in two tarpon. Her grandson-in-law hadn’t caught a thing.

Richard Winning remembers asking his mother, “Why don’t you go fish?”

“And she says, ‘Well, I wasn’t planning on fishing.’ ”

But then, his mother, an heiress to the Derby Lane greyhound racetrack and Pinellas Lumber Co., a society stalwart and civic champion, reached into her pocket and pulled out her special fishing glove.

Mrs. Winning immediately caught a tarpon.

“She was quite the fisherman,” Winning said of his mother, who won the International Women’s Fishing Association Championship three years in a row.

Mrs. Winning died July 7 after a short illness. She was 94.

Mary Margaret Winning, at left, joined friends to form a theatrical puppet troupe. “They have just finished a successful two-week engagement in the toy department of a local department store…” the St. Petersburg Times reported on Jan. 6, 1952.

Derby Lane opened in January 1925, several weeks after Mrs. Winning, then Mary Margaret Brooks, was born. She grew into the darling of Derby Lane, passing out trophies to the winners.

Mary Evertz, a former St. Petersburg Times society columnist, was younger than Mrs. Winning and didn’t know her growing up, “but I was always aware of Mary Margaret.”

Evertz first met Mrs. Winning when choosing a debutante dress at John Baldwin’s couture shop, where Mrs. Winning worked after college. Their paths crossed again and again, through Junior League and eventually through Evertz’s reporting.

“She was always a very high-profile person because of the dog track,” Evertz said.

Mrs. Winning “lived an idyllic life in St. Petersburg,” Evertz wrote in her last piece on Mrs. Winning – her obituary. It was a productive life, too. She and a friend opened a needlepoint store, she played golf, she volunteered with local civic organizations, she hosted society events at the racetrack.

And when she married Dick Winning, a car dealer, she learned a hobby she took seriously for the rest of her life – tarpon fishing.

Mary Margaret Brooks in her wedding dress in 1953. Richard Winning is pretty sure his mom got cute comments about her family business and her married last name. He sure does. (Photo courtesy Alexis Winning)
Mary Margaret Winning is pictured here with her husband, Dick Winning. He died in 1983. (Photo courtesy Alexis Winning)

Mrs. Winning’s life ran parallel to Derby Lane’s, Evertz said, starting as it did and ending around the same time.

In 2018, Florida voters passed Amendment 13, which will end commercial dog racing by 2020. Mrs. Winning hated to see the end of an era, her son said.

“It was part of the makeup for our family,” Winning said. “It took care of a lot of our family members for a long time.”

Those aren’t Winning’s only memories of his mom, of course. She was both charming and straightforward, always spoke her mind, and she was a devout Catholic who always wanted to make St. Petersburg a better place to live. And she taught him to fish.

Winning remembers how the boat would drift in Boca Grande while his parents sat, serious and quiet, waiting for a bite. For years, they’d catch the tarpon and let him reel them in.

“She really knew how to fish,” Winning said. “She was the tarpon queen.”

Mary Margaret Winning, pictured here in the ‘80s, was a mother, grandmother and great-grandmother who loved a good martini. (Photo courtesy Alexis Winning)

Senior news researcher Caryn Baird contributed to this report. Want to know more about Mrs. Winning? Head over to Instagram and @werememberthem and see one way her granddaughter will remember her. Know someone who has recently died whom we should write about? Send suggestions to Kristen Hare at

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