How Gayle Benson Became the First Lady of Football
Friday lunches at Galatoire’s are almost as legendary as the restaurant itself. Founded in 1905, the French Quarter stalwart is a hive for the social and business beau monde of New Orleans, and, while no one is exactly sure why, midday Friday has always been the zenith for seeing and being seen. This sunny Friday is no different, as the city’s gentry stabs at leafy salads and chicken Clemenceau, and giggly debutantes toast one another with flutes of pétillant pink champagne. Upstairs, amid the mustard curtains and -hunter-green wallpaper, the city’s great lady walks toward her regular table in the corner, the one overlooking the honky-tonk of Bourbon Street below.
That there is something regal about Gayle Benson is obvious the moment you meet her. It’s the serene gaze, the breathy Jacqueline Kennedy voice, the refined manner. She is the owner of the city’s two premier sports franchises (the NFL’s Saints and the NBA’s Pelicans), and as she walks down the hall to the dining room, waiters and busboys step aside. It’s like the scene in My Fair Lady when the queen of Transylvania enters the Embassy Ball and everyone bows and curtsies as she passes.
Like most royals, Benson is circumspect and impeccably polite. Also like most royals, she has been burdened by innuendo, intrusive press fascination, and heaping dollops of whispered gossip. When you are the third wife of your state’s richest man, and then you have to fend off his descendants for control of his fortune, it’s reasonable to assume that people are going to pay attention. But like all great women of style, the Chanel-swathed former interior designer—who today may be the most powerful woman in professional sports—retains a cloud of mystery she wears as comfortably as her pearls.
Talking about her childhood “across the river” in Old Algiers, a poor neighborhood, she says that from an early age “I had this eye—this desire—for beautiful things.” Her desire has been fulfilled. Her holdings include a grand mansion, a 600-acre horse farm in Lexington, Kentucky (she has raced two horses in the Derby), a home in Palm Beach, and a 145-foot yacht. (She also has one of the finest jewelry collections in New Or-leans. “Oscar Heyman, Tiffany, Van Cleef—the nice ones,” she offers demurely.)
Now, just for kicks, she’s relaunching Dixie Beer, which was first brewed in New Orleans in 1907 and which ceased production in 2005. As the widow and principal heir of Tom Benson, the car dealership and banking tycoon who owned the Saints and the Pelicans and who died in March 2018, she is now one of the wealthiest women in the world, with an estimated net worth of $3.1 billion—and the only Louisianan on the Forbes 400.
Gayle Benson’s journey to becoming the Crescent City’s figurative first lady is a distinctly Southern tale of determination, opportunity, and unlikely romance. She was a girl from the wrong side of the bayou who defied society’s expectations of what a young lady could and should aspire to. She charmed the most obstinate mogul in New Orleans and then endured tabloid stories implying that she was a gold digger who had welshed on her own past debts. Today she is a 72-year-old socialite who is making her presence known in the -testosterone-fueled world of professional sports.
“During the last year of his life, Mr. Benson would say, ‘I’m not going to live much longer. Promise me you’re going to take care of Mrs. Benson,’ ” Saints president Dennis Lauscha recalls. “But she’s her own woman. We take strength from her.”
Gayle Benson’s mansion sits on a private road in Audubon Place, the toniest neighborhood in New Orleans, where her neighbors include Avram Glazer, the co-owner of both the Tampa Bay Buccaneers and England’s Manchester United soccer club, and John Georges, the owner of the Times--Picayune. The street is a picturesque tableau of stately houses with wide porches and white columns, manicured lawns, and window boxes overflowing with hydrangeas and roses.
Perched on a French provincial chair in her sitting room, Benson wears a black crepe top and flowing pants from Chanel paired with a fitted white blazer from Alexander McQueen and…post--surgery shoes. She has had trouble with both feet, and she had them operated on simultaneously, because Gayle Benson always wants anything unpleasant dispatched with as quickly as possible, down to her toes.
She grew up on the west bank of the Mississippi River, one of three children of a supervisor at a pipe-fitting company and a homemaker. She worked as a secretary, and at the age of 27 began buying and flipping houses, long before many people were doing it. From there she moved on to opening a design business. “I was always entrepreneurial,” she says, “even in grade school.”
It’s not an exaggeration to say that God brought her to Tom Benson. In 2004, the notoriously grumpy 77-year-old tycoon was at home, puffing and blowing on an exercise bicycle and -watching the morning Catholic Mass on television; she was serving as a lector at the service, and he saw her on TV. The next day the widower decided to travel to the church himself for a closer look. He liked what he saw. She didn’t. “He looks at me and goes, ‘Who’s this young lady?’ He puts his hand out and I put my hand out,” Gayle recalls. “I looked into his big blue eyes and I said to myself, ‘Buddy, I’m not interested in you.’ He looked like trouble to me.”
He was. With a foul temper and controlling demeanor, Tom Benson was notorious for being a sore loser and “a grudge holder. If you did something wrong, he remembered forever,” Gayle says. Already twice divorced, she was not interested in romance. She also found his boasting—about his wealth, his possessions, his business acumen—off-putting. “The more he talked, the less impressed I was,” she says. “I’m thinking, This guy is too shallow for me.”
But she had dinner with him, which led to another, and then another. Despite herself, Gayle found herself disarmed and falling for his sense of humor and courtly manners. “Gayle was able to bring out the best in him,” says New Orleans archbishop Gregory Michael Aymond, who watched the couple’s romance blossom from the beginning, “and help him develop that more gentle side.”
Tom Benson hardly underwent a Scrooge-style transformation (once, during a dinner party, he got so bored he abruptly ended the evening by standing up and declaring that it was time for everyone to leave), but there was, those who knew him say, a softening to his prickly demeanor. “He was high for the wins and low during the losses,” says Mickey Loomis, the Saints’ general manager for almost 20 years. “She’s less emotional, more even-keeled. He admired that.”
When the couple got engaged in 2004, Gayle’s friends worried that Tom’s daughter and grandchildren from his first marriage might not accept his new wife. Angela Hill, a local television anchor who befriended Gayle in the mid-1970s, made a point of publicly toasting not what Tom was bringing to the union but what Gayle was: trust, loyalty, friendship, unconditional love. “When I said that at the rehearsal dinner, it was really targeted toward—certainly to Tom, but to his family, too,” Hill says. “I hoped that they would embrace her. It didn’t work out, and frankly it’s their loss.”
Tom’s daughter Renee Benson LeBlanc, granddaughter Rita, and grandson Ryan had all been deeply involved in the family business, but it was Gayle who helped Tom get through the aftermath of Hurricane Katrina and “Bountygate,” a 2012 scandal on the Saints that involved secret bonuses being paid by coaches for injuries inflicted on opposing players. (Tom was not implicated.)
LeBlanc and her children accused Gayle of turning him against them, so when Tom announced in January 2015, at the age of 87, that he was disinheriting them and leaving his entire estate to Gayle, they filed suit to have him declared incompetent. In the process they dug up embarrassing details from Gayle’s past, including an alleged arrest and lawsuits stemming from accusations that she hadn’t paid various wages or taxes during her time as an interior designer. Among other transgressions, the suit alleged that Gayle had “systemically isolated Tom Benson to prevent him from his usual interactions with family, friends, and advisers, thereby allowing her to unduly influence his decisions to her benefit.” The tabloids feasted. Tom died in March 2018, at age 90, from influenza.
“It’s hurtful, but you need to move on,” Gayle says today. “I try not to get angry, or stay angry.” (Attorneys for the LeBlanc family did not respond to requests for comment for this story.)
The lawsuit wasn’t the first time the family had made waves. Observers say that while New Orleans society eventually warmed to Gayle, the family’s infighting was never a secret. Tom’s daughter and grandchildren accused Gayle of cutting off access to the patriarch to gain power; in a deposition Tom testified that they had physically assaulted Gayle in a luxury suite at a Saints game and had “tried to kill me.”
If Renee Benson and her children thought they could turn the tide of public opinion by playing the wicked stepmother card, they misjudged the mood of the city, which rallied behind Gayle. “She had so much support publicly,” says Mike Triplett, a journalist who has covered the Saints since 2005. “The team was so vocal in siding with her, and how she was the one they wanted to be the owner and how Tom was grooming her to be the owner. I think the fan base had gained confidence in her.”
So had the players. “She is one of the kindest people I’ve known,” says Saints quarterback Drew Brees. Gayle is godmother to one of his children. “She makes her players feel special, whether it’s leaving signed mail clippings on our lockers or interacting with our families at practice. My wife and kids adore her.”
Chatter on the city’s social circuit is more mixed. “Gayle has remade herself into Lady Bountiful, and she sure as shit has a lot of power,” says one society fixture. “But no one in the whole scenario looks good.”
After years of ugly litigation—which reportedly included a secret recording made by Rita to prove that her grandfather was losing his mind and an explosive deposition in which Tom Benson shouted, “Lying bastard!” at Ted Bloch, a psychiatrist the LeBlancs hired to affirm his senility—the court awarded Gayle ownership of the family’s sports franchises. Today she is one of a small group of women who oversee an NFL franchise, a sorority that includes 94-year-old Martha Firestone Ford of the Detroit Lions; Kim Pegula, 50, who co-owns the Buffalo Bills with her husband; and 60-year-old Jody Allen, who is chair of the Seattle Seahawks, which is owned by a trust in the name of her late brother, Micro-soft co-founder Paul Allen.
There are fewer gatherings more mysterious than the seasonal meetings of the NFL owners, but if you imagine an old girls’ network huddled in a corner, you’ll be disappointed. For her part Benson keeps counsel with, and trusts, the same men her husband did: the ones who still run the Saints.
By her own admission she doesn’t often hold court at the meetings (“I will write letters if I feel I need to”), but she makes sure that she is heard. When San Francisco 49ers quarter-back Colin Kaepernick set off a firestorm by kneeling during the national anthem during games, and other players followed suit, Gayle—-representing an ailing Tom in 2016—cornered NFL commissioner Roger Goodell. “We were getting ready to start the meeting,” she recalls. “I said, ‘Roger, you need to tell these owners that their players will not kneel. That’s all you have to do.’ ”
He didn’t. The kneeling controversy has quieted down; Kaepernick became something of a social justice folk hero, though he remains unsigned by any NFL team. But in making her voice heard, then and since, Gayle Benson has established a presence (in the NBA as well) that is far more steel magnolia than shrinking violet. And she is building her teams for championships. “We can’t always win,” she says mischievously, “but I kind of hope we do.”
This story appears in the February 2020 issue of Town & Country. SUBSCRIBE NOW
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