How Charlotte Jones Anderson Became The NFL's "Ivanka Trump"

Charlotte Jones Anderson believes that the pregame huddle is the "perfect symbol" of American football. "It’s a gathering of men that come from completely different walks of life and believe in completely different things, but they put those beliefs aside to put everything that they have on the line for each other," she tells me over video chat, perched in her pristine office at the Dallas Cowboys world headquarters in Frisco, TX.

This "gathering of men" conjures sepia-tone images of players in a circle, close enough to touch helmets. With their backs to the outside world, they chant aggressively — sometimes memorized poems, or call-and-response phrases — as they prepare to take the field. While Charlotte sees unity in men flocking together, huddles are also very insular.

"They need each other in order to be successful…" she says, earnestly. "So they check whatever differences they have at the door."

If anyone is qualified to wax poetic about football, it's Charlotte Jones Anderson, 51 — daughter of Jerry Jones, one of the most famous team owners in the NFL. As the Dallas Cowboys' executive vice president and chief brand officer, she oversees all of the business operations surrounding the franchise, including brand marketing, fan engagement, stadium design, entertainment, and licensed apparel. But lately, as the league has become entrenched in hugely polarized, headline-making political debates, image and optics are top of mind.

Last year, NFL TV ratings dropped 9.7% during the regular season. In May of this year, the NFL announced a new policy to fine players who protest during the National Anthem. And on Wednesday, a former Dallas Cowboys cheerleader filed a federal lawsuit against the Cowboys alleging that she wasn’t paid for overtime work, and made less money than the mascot. Still, Charlotte insists that football fans and teams are more united than ever. "Through the last year and before, we saw that the true value of our game is really about unification," she says. "I dare say, our game is actually the only thing right now on the landscape that is actually bringing people together instead of tearing people apart."

But can "the game" be separated from "the landscape"? Last fall, when quarterback Colin Kaepernick’s take a knee protests gained national attention, NFL teams had to make a very visible decision: stand for the anthem, or follow Kaepernick's suit and make a statement in solidarity. Each team did something slightly different during the first week of the regular season. One Philadelphia Eagles player raised a fist while his teammates placed their hands on his shoulder. Ten San Francisco 49ers kneeled for the anthem. The Raiders running back sat during the anthem. And nobody on the Cleveland Browns sat or kneeled.

But in week three, President Trump got involved. On September 22, 2017, three days before the Cowboys' played the Cardinals, President Trump brought up Kaepernick's protests during a rally in Alabama. "Wouldn’t you love to see one of these NFL owners, when somebody disrespects our flag, to say, 'Get that son of a bitch off the field right now. Out! He's fired. He's fired!'" he said.

Charlotte says the demonstrations became divisive, as opposed to unifying. Though Kaepernick communicated that he was protesting police violence against people of color, Charlotte believed the gesture "actually meant so many different things to many different people." The Cowboys execs wanted to let their players fight for something, but they couldn’t agree on what the protests represented, she says. "To some, it was about police brutality, for some it meant equality, and for some who were observing [the protests], it meant you’re standing against our flag," she says.

The Cowboys were faced with a dilemma: respond or do nothing. And on game day, as Charlotte and the team traveled to Phoenix, the pressure was on her and her dad to call the play. "Charlotte is a crisis consultant," says Meredith Counce, director of brand strategy at the Dallas Cowboys. "When it’s not as smooth of a ride as you maybe would like for it to be, that's when she shines. And I think everybody does always look to her to be that rock solid, smart sounding board for everyone to turn to."

Sometimes, Charlotte's position requires her to be the pretty face for an ugly industry — a welcoming hostess in the divisive house her father built. For as fervent as Dallas Cowboys fans are, there are just as many people who have despised Jerry for decades.

In the '80s, Jerry Jones was a passionate sports fan from Arkansas who made millions off of an energy exploration firm that he founded, called Jones Oil and Land Lease. In 1986, Jones was bought out for $175 million dollars, and three years later, he decided on a whim to buy the Dallas Cowboys for $140 million.

At the time, Charlotte says the franchise was a "sinking ship" that was losing $2 million a month due to poor financial planning. The team was also losing on the field, with a 3-13 record. In a 1984 story in the New York Times, President Trump said he considered buying the Cowboys, but chose not to because they were so bad. ''I feel sorry for the poor guy who is going to buy the Dallas Cowboys," he told the New York Times.

Back then, Charlotte was working as an assistant to Republican congressman, Tommy Robinson in Washington D.C. It was her first job out of Stanford University, where she majored in human biology with an emphasis on organizational management, and she wanted to make sure she was doing something impactful with her life. "Washington's the place you go to make a difference," she says, laughing. "I learned really quickly that maybe that wasn't really always the case." She didn't know anything about football or professional sports, nor did she have any desire to work for her dad. "The last thing on my mind was wanting to be part of the family business," she says.

But in 1989, while the team was in Washington D.C., Charlotte got a call from her father, who was in the middle of a feud with the Dallas Cowboys cheerleaders over their uniforms. The Chicago Tribune reported at the time that 14 cheerleaders resigned because Jerry was allegedly going to get rid of policies about fraternizing with players, and change the iconic Cowboys uniforms from "hot pants" to "skin-tight Spandex shorts."

Frazzled, he asked Charlotte to help settle the angry cheerleaders who had lined up outside his office. Charlotte, who has a background in dance and an eye for fashion, says she showed up and discovered that the uniform thing was just a rumor, "just like most of everything else was at the time," she says. Jerry saw how she swiftly fixed the problem, and asked if she would consider working for him full-time. "He was like, I just need people that I can trust, because it was a really intense time," she says.

When Jerry took over the team, he effectively cleaned house, replacing longtime employees with his friends and family. Charlotte says it was an ugly time with "a lot of people suing each other." "I think he was just trying to have people around him that would tell him what he needed to hear, not necessarily what he wanted to hear," she says. Within nine years, the Cowboys became a family business. Charlotte’s older brother Stephen Jones was already working for their dad, and two years after Charlotte joined, so did their younger brother, Jerry Jones Jr. “When you see somebody sinking, you just jump in to try to help,” she says.

As the story goes, Jerry first told his daughter she had two jobs: Find a way to stop losing money, and don’t tarnish the star, referring to the Dallas Cowboys' iconic logo. Financially, they’ve since been able to “right the ship,” as Charlotte says. In 2017, Forbes reported that the Dallas Cowboys were worth $2.4 billion, with an annual revenue of more than $100 million, making it the most valuable sports team in the world.

And it's clear why Charlotte would excel at her other responsibility. Over video chat, she's polite, cheerful, and speaks with a sweet southern accent, but knows when to turn staccato or pivot away from thorny topics. She reminds me of The Warden in the movie Holes — meaning, I wouldn't mess with her — but maybe it's just the accent, red hair, and painted fingernails. "Being in this male dominated world, but still being a beautiful, feminine woman; I think she's mastered that balance," Counce says. "She doesn’t have to be the loudest voice in the room for people to hear her — she's earned the respect."

As a female executive for one of the most popular football teams in the country, Charlotte has a say in the decisions that the business makes on a daily basis. She hosts a periodic all-staff, women-only meeting during which various departments pitch ideas to her about how the franchise should target women. "Charlotte gives us a voice here," says Lindsay Cash Draper, a reporter and host for the Dallas Cowboys’ media network.

And as the daughter of the owner, she also conveniently has the boss' ear and his respect. Charlotte's mother, Gene Jones, former Miss Arkansas, is the only other woman in their nuclear family, but she never got involved with the football team. In an interview last year, Jerry referred to her as "the backbone of the family," but said she prefers to stay out of the spotlight when she can.

Charlotte, on the other hand, has chosen to take a public position. "She is the NFL goddess, seriously," Draper affectionately says. But in a league riddled with politicized controversy, Charlotte’s role as the attractive, educated, woman who smoothes out painful debates involving her father, reads like the Ivanka Trump of the NFL.

On September 25, 2017, the Cowboys played the last game of the week, which bought them a few more hours to mull over how they would handle the protests. In the locker room, about five minutes before the anthem, Charlotte, Jerry, and the players made a unanimous decision to march onto the field together. With the execs in the middle flanked by players on both sides, they'd link arms, kneel, and then stand when the anthem began. "That in and of itself created its own controversy," Charlotte says.

The reactions to their demonstration were mixed: a writer at GQ said Jerry looked "self-satisfied" and didn’t deserve the praise, and Deadspin called the whole thing bullshit. In fact, Refinery29 published an article about the significance of the demonstration for Texas, a traditionally red state. "We saw the Cowboys stand together against police brutality, and stand in support of Kaepernick's message that Black lives do matter," Megan Fredette wrote.

Nobody could agree whether the Cowboys were complicit, purposefully lukewarm, or downright hypocritical. And maybe that perceived ambivalence was the whole goal of their strategic choreography. But the following Sunday, when Vice President Mike Pence made headlines for exiting a 49ers game after players took a knee, Jerry told ESPN that Cowboys players who did anything "disrespectful to the flag" wouldn’t be allowed to play. "If we are disrespecting the flag then we won't play. Period," he said. The next day, President Trump tweeted his approval: "A big salute to Jerry Jones, owner of the Dallas Cowboys, who will BENCH players who disrespect our Flag."

“Nobody woke up realizing we were going to be in a controversy of that magnitude,” Charlotte says.

After that back-and-forth with Trump, Jerry — who has been criticized for being incompetent, hypocritical, and a relentless meddler — was an easy target for sports journalists and critics who were angry with the duality of his actions and words. "I don’t think any of us like criticism at any level," Charlotte says. "I think we try to appreciate constructive criticism, and then it gets to the level of just hateful criticism."

Now looking back, there’s solid evidence to believe that this particular criticism was warranted, because President Trump and Jerry go way back. In 2016, Jerry appears to have donated $1 million to Trump’s inaugural campaign under the organization, "Glenstone Limited Partnership." And, during a hearing for Kaepernick’s grievance case against the NFL last month, Jerry said under oath that President Trump had called him to say that the protests were essentially futile. "'This is a very winning, strong issue for me,'" Trump told Jerry. "'Tell everybody, you can’t win this one. This one lifts me.'" Charlotte’s political stance, on the other hand, is unclear.

Charlotte is proud of her dad, and the empire that they've built together. She describes him as an eternal optimist. Growing up, he traveled a lot for work, she says, and if money was tight, he would hide it from the kids. "That sense of excitement, and wonder, and a better day everyday shielded us from the negative, and he still does that today," she says. Even during times of crises, she relates, Jerry will sit back, move his fingers back and forth by his ears, and say, "'That’s the world’s smallest violin. No one feels sorry for you. Get over it, move on — can you believe we get to do this everyday?'"

That determined, stoic optimism is what gets Jerry through the tougher days of the job, according to Charlotte. In the beginning, when something would go wrong, Charlotte and her five family members would turn to one another, and say, You okay? Okay. "You kind of turn to inner-strength and face forward," she says. Nowadays, it's harder to take care of issues because the family and business have grown, along with the problems they're forced to face.

Recently, Jerry has been under fire for publicly supporting Ezekiel Elliot, the running back for the Dallas Cowboys who was accused of domestic violence. (As an organization, the Dallas Cowboys have publicly supported organizations that provide counseling and shelter for survivors of domestic violence and sexual assault.) After a yearlong investigation, Elliot was only suspended for six games. Jerry paid the NFL $2 million for the legal fees involved in the case, and to this day he insists that Elliot "paid the most level of punishment that I've seen for what he did."

And in April of this year, the New York Times published a story about NFL cheerleaders who said they experienced sexual harassment while on the job. Some say that they were forced to pose for topeless photoshoots, and others filed lawsuits stating that the rules about physical appearance were discriminatory. In the New York Times story, an unnamed Dallas Cowboys cheerleader said that a fan for an opposing team once yelled, "I hope you get raped!" to her at a mandatory tailgating event. The Dallas Cowboys did not respond for comment on that story.

When I asked Charlotte if she thought the coverage was fully representative of the ways NFL cheerleaders are treated, she told me that she couldn't give a blanket statement on behalf of the entire league, but that she personally "hates that that element is out there." “I would hope to think that stories that women talk about portray what actually goes on in their world, and through their eyes," she says, slowing her pace and choosing her words carefully. "I think we have a tremendous amount of respect for who they are."

Charlotte goes on to mention that Dallas Cowboys Cheerleaders have their own reality TV show on CMT called, "Making The Team," which Charlotte claims is an accurate portrayal of what it’s like to be on the team. "Women are a very important part of our organization, and I think they feel that value," she says. "We’ve always had an open door policy to be able to say if something is [wrong]... but more importantly, how do we make [the franchise] better?" (We reached out to the Dallas Cowboys for comment on the former cheerleader who filed the federal lawsuit this week, but did not receive a response at the time of publish.)

People often ask Charlotte what she worries about at night. "It's not what you worry about when you go to bed, you worry what you’re going to wake up to," she says. And as her team and her beloved sport get more political, her "huddle" looks less like well-meaning men committed to a common goal, and more like a group of people asleep to the injustice around them. So where does that leave Charlotte? Clearly, she has the power to make changes within her franchise. But what obligation does she have to challenge the culture of the sport?

"In society, we have a tendency to accept behavior of men and if women exhibit the same behavior, we don’t think that’s proper. we don’t think that’s right," she says, when asked if the cheerleaders were held to a higher standard than players because they're women. "I do think however, that we should also empower women that grace is still a great thing. You can still succeed and be successful, and you don’t have to lose the grace of what you do value about being female."

The question remains if the Cowboys can handle a female leader like Charlotte — who is equal parts grace, legacy, and power — to call the plays on her own. Jerry has often said that he has no succession plan, because, "I don’t ever want to quit.” But, Charlotte’s daughter Haley, 25, the oldest of her three kids, has expressed an interest in pursuing sports management, which she says signals a cultural shift: "It gives me a great sense of pride in seeing how the landscape is opening to allow women to be part of the game."