Photo by Jared Thomas

By Bill Burrus

It was a soul-jarring wakeup call that led directly to Charlie Winfield making a bold move. 

Just moments after a Mississippi State basketball loss in 2023, Winfield, a passionate Bulldog since birth, hurled his cell phone across the room at the fireplace in his den. Then it was the words from his wife Jennifer that made Winfield decide to quit talking and start doing.

“We had lost by like 10 points on the road in basketball,” Winfield recalls, “and I said, ‘we’re never going to win unless somebody does something.’ And my wife looked at me and says, ‘well, what have you done.’”

It was the wakeup call he needed. 

So the next morning, Winfield began the process of putting together and running the Bulldog Initiative, LLC — which supports Mississippi State athletes by assisting them in monetizing their Name, Image and Likeness (NIL) rights. 

“After a couple of false starts, and some other people trying to be involved, I saw that Mississippi State didn’t have anything going, and it didn’t have a plan or anybody taking charge,” Winfield said. 

So he put his money where his mouth is and jumped in feet first into the murky waters of NIL. Soon, Winfield and others across the Southeastern Conference had no idea how quickly things would change on this front.

“A lot of people thought that NIL was just going to mean that we were helping with endorsement deals. They thought it was gonna be somebody doing a deal with a local business or somebody doing a deal with maybe even a national business,” said the Starkville attorney. “But it pretty quickly changed and became a thing all around the country.”

Change has been the one constant in the world of NIL. Winfield said he and his staff work hard to stay on top of the ever-shifting pay-for-play scenario.

“Change we expected, but I have been surprised how fast and frequent it has come … To make it this way, but everybody thought that there was going to be strict regulations. And then ultimately, enough people quit following, enough judges said that you can’t do it. The NCAA couldn’t impose the rules it was trying to impose, that they were just more of the same. More of the same type of violations that got him in trouble to begin with.”

The Starkville attorney is a Birmingham, Ala., native who grew up in the shadows of Davis Wade Stadium in Starkville, graduated from Starkville Academy, attended MSU, where he was active in the Sigma Chi fraternity, and then finished his education at Notre Dame law school. He grew up mimicking the late, legendary play-by-play man Jack Cristil and dreaming of being a Bulldog athlete one day.

Let’s let Winfield take it from here: “Well, right or wrong, there are very few things in my life other than my faith, my family and my reputation that mean more to me than Mississippi State. And to me, when I was a kid, I wanted to be a Mississippi State football player. And if you’ve ever seen me, you know that doesn’t work. I wanted to be a Mississippi State baseball player, but I couldn’t hit a curveball. For obvious reasons, that didn’t materialize, but it was my chance to try to have an impact in a different way.”

Winfield said his early efforts to raise funds received a huge spike in funds in late October of 2022, when athletic director John Cohen left Mississippi State for the same position at Auburn.

“There’s no question (Cohen’s departure) had an impact,” Winfield said, “but it wasn’t the only reason for the recent NIL growth at MSU. I think the other part is once we were able to explain to people the true situation of where we are, they realized that we really weren’t in as negative a spot as people like to think or perhaps was portrayed. If nothing else, it got people a little bit competitive. It got attention for it, and that’s the biggest thing — it got people just spreading the word.”

Many have questioned how sustainable this type of alumni giving is moving forward. Winfield has a message for those people.

“At the start, there were plenty of people who felt that way, but if you look across the country, more and more, what we’re seeing is that people, and college towns in particular, are starting to see the benefits more than ever in terms of teams and its impact on the local economy. It’s a fact when you host a playoff game, it matters when you have big crowds on the weekends, and it matters for those businesses. And I think at some level, right, there is a limit to what can be done, but I do think the spending it where it is, is way more sustainable than most people ever imagined.” 

NIL money began to flow heavily into baseball once Brian O’Connor left Virginia, where he spent 22 seasons and amassed more than over 900 wins and made seven College World Series appearances, for Starkville this summer.

“Well, I think anytime you see a change that the team can get a surge of energy, and Brian O’Connor is an example of one of those times where Mississippi State just went out and acted like a blue blood in baseball and went and took one of the best coaches from another Power 4 school. And I think there’s some sense of pride that comes with that.”