Meet Skylene Montgomery: Sean Payton's fiancée on life as a tomboy, pageant queen, fitness buff

EDITOR'S NOTE: This profile was originally published in December 2019. Skylene Montgomery and Sean Payton were married June 18, 2021, in Mexico.

Just over a month ago, Saints fans got an up close and personal look at Skylene Montgomery when, during a timeout in a home Saints game, the smiling brunette was caught on the Mercedes-Benz Superdome Jumbotron with the caption: "The Future Mrs. Skylene Payton."

Montgomery, watching the game from her fiancé’s suite, was taken by surprise.

“I thought they were moving in on Vince Vaughn,” said Montgomery, who was seated next to the actor during the game.

“Skylene is not someone who seeks the limelight,” says her friend Jennifer Ansardi, a local artist who met Montgomery at the Super Bowl party thrown by host city New Orleans in 2013 and describes her as “independent and wise, poised, caring and fun.”

But "she can handle any emergency with something in her purse. If you have a blister from your shoe, she has a Band-Aid; if you break a strap, she has tape or a sewing kit," Ansardi said.

Yet inquiring minds want to know more. As the popular T-shirt indicates, the Saints are the heartbeat of New Orleans. And what has more heart than an impending wedding?

A surprise proposal

Montgomery opens the iron gate to her Uptown home wearing an oversized white shirt, jeans and shiny gold Angela Scott monk-strap oxfords. Her dark hair is swept up in that casual chic way, large matte-gold hoops framing her beauty queen face.

As Montgomery reaches down to settle the two dogs that have followed her to the gate, a glimmer of light flashes on her left hand. The emerald-cut diamond on Montgomery’s ring finger was given to her by Payton when he surprised her with that proposal Nov. 8 at a private party at Longway Tavern in the French Quarter.

“That’s big enough to fry an egg on,” said country music artist Heidi Newfield when she saw it. The singer was there with her band to provide the musical background for the occasion.

By now, everyone knows how the Saints head coach created what social columnist Nell Nolan described as “an elaborate shell game.” Saints owner Gayle Benson had invited Montgomery to what she billed as a celebration of the 15th anniversary of her marriage to Tom Benson, who died in March 2018. Other guests (including Montgomery’s parents and friends Payton had flown in) were told they were attending an early surprise party for Montgomery’s 35th birthday.

But when Newfield began to sing her 2008 hit “Johnny and June,” and Montgomery looked over to see her boyfriend, dressed in all black, she knew there was more going on. Payton dropped to one knee.

"We were in on it, and Sean had asked for our blessing," said her mom, Darlene Montgomery, who with husband Skylar witnessed the look of total surprise on her daughter's face.

Gayle Benson was delighted as well.

"Skylene has been a part of our Saints family for many years," Benson said. "I am so thrilled for Sean and Skylene on their engagement, and I enjoyed being part of the engagement night planning."

A personal anthem

The partnership of Skylene Montgomery, 35, and Payton, 56, has been solid for years now. A permanent, but more subtle, symbol preceded that brilliant diamond.

On Montgomery’s left ankle is a “J” tattoo. Payton also has one on his ankle. What those two J's stand for became evident during the surprise proposal when Newfield sang the lyrics to the song that has been a personal anthem for the couple:

“I wanna love like Johnny and June/rings of fire burnin’ with you/I wanna walk the line, walk the line till the end of time.”

This will be Montgomery’s first marriage, and Payton’s second. The bride-to-be said the two have tentatively set March 2021 for a New-Orleans-style wedding.

“Short of my being on his insurance, and having a big ol’ rock on my hand, nothing will really change when we marry,” said Montgomery, who is not yet sure if she will change her last name.

The two met at a Saints-Panthers game when Montgomery was a nurse living in Charlotte, North Carolina.

Montgomery had asked a friend if he could get tickets for her and some co-workers for the game. Instead, he gave Montgomery a phone number and told her to make the call. The number he gave her was a direct line to Payton.

It was during the pregame ceremony that Montgomery met the NFL coach for the first time. The two had a short conversation when she thanked Payton for the tickets.

“Now you can be a Who Dat,” Payton said.

“A Who What?” she had replied.

Baseball to beauty pageants

Montgomery was an only child, born to Skylar and Darlene Montgomery, of Parkersburg, West Virginia, where she grew up a self-described “tomboy” in a middle-class family, her father the co-owner of a garage-door supplier. Her distinctive first name combines those of her parents.

“I had a bowl-cut haircut and was that kid in messy baggy shorts and a Nike tee who played baseball,” said Skylene Montgomery.

She was competitive in sports, but also naturally kind, her mother recalled. "She always gravitated toward the new kids in school, to make sure they felt comfortable," Darlene Montgomery said.

Darlene Montgomery encouraged her to take dance lessons but surrendered to her daughter’s athletic achievements as an all-state volleyball and softball player.

When Skylene Montgomery hit ninth grade, however, something changed. She entered her first beauty pageant, Miss Teen West Virginia, open to girls 13 to 18 years old. The then 14-year-old, who had hit her maximum height of 5 feet 7 inches in fourth grade, came in first runner-up to an 18-year-old.

Montgomery continued entering festival pageants and accumulating scholarship money. In 2008, as a Marshall University graduate with a degree in exercise physiology, she was crowned Miss West Virginia USA. She got a nursing degree from West Virginia University and moved to Charlotte, where she worked two jobs to pay off student loans.

“I did a lot of growing up during that time,” said Montgomery, who credits her parents with teaching her independence. Her father once refused to help her out when she had mismanaged her money and had her cellphone turned off, telling her she would just have to wait until her next payday.

“I was never late on a payment again,” she said.

In 2013, Montgomery moved to New Orleans to work in the gastrointestinal intensive care unit at Ochsner Medical Center. She is now studying to become a nurse practitioner and said she will take a more active role in the Sean Payton Play It Forward Foundation, in addition to working with Saints owner Gayle Benson on the annual Moonlight & Miracles Ball to benefit Ochsner Cancer Institute. She and Payton will host the Harvest at Home signature fundraiser for Second Harvest in the spring.

Home is where the heart is

Montgomery and Payton have shared three addresses, one in the Warehouse District, then a three-bedroom condo in the converted New Orleans Center for Creative Arts school Uptown and now their new Uptown home, a 6,000-square-foot Greek Revival they recently purchased. A giant StairMaster sits in the empty living room alongside stacked boxes, as workers come and go. The process of moving in is just beginning.

“We forgot to specify to the movers that the workout equipment goes upstairs,” said Montgomery, as she heads into the great room filled with light from walls of windows facing the saltwater pool. Pups Frannie Grace (a sheepadoodle) and Murphy (a goldendoodle), named for CrossFit workouts Montgomery and Payton have shared, settle on one of the large sofas.

Payton often joins in her fitness routine, which also includes boxing classes and hot yoga. Golf is another shared activity.

Several mornings a week, Montgomery — in workout gear with hair pulled back under a backward ballcap — enters a warehouse space for boxing sessions with trainer Keith Director. The music is loud, and the workouts are tough. 

"She's talented. She works hard. She's just good! Strong. Fast. Lean," is how the trainer describes her.

A workout consists of slamming 65-pound "battle ropes" against the floor to strengthen upper body and core, doing weight work, jumping rope, working out with resistance bands and finally sparring with her coach.

Montgomery wraps her hands, as boxers do, before slipping beautifully manicured fingers into white boxing gloves, then begins to pound the padded mitts Director holds up to catch her targeted punches.

Behind them on the wall are two pairs of boxing gloves, one signed by Sugar Ray Leonard and another metallic gold pair thrown from a Bacchus float. Mounted just below the gloves are two eye-catching Muses stilettos, sequined by Montgomery herself.

"When you're finished, you're gassed, exhausted to capacity," said Director.

Decision time

Fitness is not the only reflection of the newly engaged couple's compatibility.

“I make a decision every 15 seconds,” Montgomery recalls Payton telling her when the two started decorating their previous residence together. She matched his pace.

“We picked out everything — cabinets, countertops, floors, tile — in one hour,” she said. “We are both ‘yes’ or ‘no’ on decisions like that.”

But there are differences in their demeanors. She describes him as “neat and meticulous” with “attention to detail” but sees herself as “freestyle” or a “controlled mess.”

Her future husband’s creativity is one of the traits she admires most about him.

“He never ceases to amaze me, the way he can give life to inanimate objects," she said. If he weren't a coach, he could be an author, she thinks. "The way that he tells stories and presents things is amazing,” she said. “That’s probably why he is a good coach or, as he calls himself, a teacher.”

All things New Orleans

It was love at first sight when Montgomery moved to New Orleans.

She was quick to learn the city's quirky pronunciations and spellings; after all, Tchoupitoulas Street was her first address. She got used to seeing people at Rouses in costume at noon on a Tuesday, parades popping up anytime and anywhere. She found that food is the best way to get to know the culture.

When Montgomery was in the Miss USA Pageant, the feedback from judges was that the trim beauty was “too muscular.” But being a foodie in New Orleans has added almost 10 pounds to the toned and trim frame she maintains.

“When we go out, chefs are always whipping up things for Sean,” said Montgomery. Her favorite local food is crawfish, so much so that she has shipped the New Orleans staple back to West Virginia to share with family and friends.

The couple is often seen at Irene’s restaurant in the French Quarter, and in their neighborhood, they frequent such eateries as Clancy’s and Saba. Montgomery also loves to cook.

When Payton gave Montgomery a diamond and gold fleur-de-lis pendant on her 30th birthday, she knew she was an official member of the Who Dat Nation.

Montgomery’s Saints T-shirt inventory consists of about 10 she purchased for herself and perhaps another dozen Payton gave her. Friend Ansardi says Montgomery has such a distinctive sense of style she could be writing her own fashion blog, and she puts together her own ensembles in black and gold. But Montgomery is not one to deem an outfit lucky.

Superstitious or not, on those dark days when the Saints have lost, Montgomery has embraced a team lesson.

“Early on, being a nurse and a fixer, I wanted to make it better,” she said. But she figured out that listening was the better approach when a coach is down, and took to heart his mantra.

“ 'You have until Sunday at midnight to celebrate or pout. Monday you have to start on the next week.’ ”