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Stefon & Trevon Diggs: Building the Family Business

The Diggs brothers may play for different teams, but they work together. The pair discuss their partnership with Saxx Underwear, building generational wealth, and more.

Born five years apart, Stefon and Trevon Diggs have never played together or lined up against each other in an official game. Unless you count pickup football or basketball, which they certainly do.

Buffalo Bills wide receiver Stefon and Dallas Cowboys cornerback Trevon are as close as they are competitive. Growing up, Stefon not only served as big brother, but also as a father figure to younger brothers Trevon and Darez. That responsibility fell to him after their father, Aron, died of congestive heart failure in 2008. 

While Stefon and Trevon forge their own paths to NFL stardom, the brothers rely on each other on and off the field.

“I feel like the older you get, the more information you should be consuming as far as learning and trying to avoid as many mistakes as possible,” Stefon, the more vocal of the two, told Boardroom. “The best way to do it is for me to go through it, then at the end of the day when it’s his turn, he won’t necessarily have to do a lot of things I had to go through. It’s a part of the learning curve.”

Stefon Diggs’ signed a four-year, $96 million contract with the Buffalo Bills in April. (Douglas P. DeFelice/Getty Images)

Stefon, who turns 29 on Nov. 29, has begun to further his interests, investments, and influence after establishing himself as one of the NFL’s top receivers. A fifth-round pick to the Minnesota Vikings in 2015, Stefon led the NFL in receptions and receiving yards in 2020. It not only earned him his first Pro Bowl and first-team All-Pro honors, but also a four-year, $96 million contract with the Bills that keeps him in Buffalo through 2027.

A year later, Trevon, Dallas’s second-round pick in 2020, led the league with 11 interceptions, including seven in the first six games of the season with two returned for TDs. He was also named first-team All-Pro and reached his first Pro Bowl that season. The 24-year-old is in the third year of his four-year, $6.3 million rookie contract. He can become an unrestricted free agent in 2024.

“Considering that my brother is kind of young right now, his main focus has been for the most part football,” Stefon said. “You have to make sure your first hustle is always working for you. I’m a little older than him — I’m not that old — but I’ve been stepping out into the realm of more business-oriented things, not only as far as real estate, but I have a lot of things on my plate I’m trying to do. There’s a lot of things I’m trying to bring home as far as Black-owned businesses and creating new avenues and new streams of income. It’s more so bringing him along. I just want him to focus on football right now. One thing at a time. 

“I wish I had me when I was his age to be brought along, but definitely there will be a lot more business going in the future. I’m more so focused on commercial real estate than anything.”

Trevon Diggs, 24, is in the third year of his rookie contract with the Dallas Cowboys. (Photo by Rich Graessle/Icon Sportswire via Getty Images)

Trevon recognizes the benefits to watching his big brother go through the learning process.

“It helps out a lot as far as our careers,” Trevon said. “Whether it’s involving football, life or anything, he’s done it. It’s a blessing just to have him in my corner and to be able to follow his lead.”

Stefon and Trevon called upon one another as part of a partnership with Saxx Underwear. The brothers were named Chief Ball Officers with the brand in late August ahead of the 2022 NFL season.

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While it’s more of a traditional athlete-brand partnership to start, there is potential for the brothers to become more involved. One possibility is for them to create specific products or lines based on their respective positions on the football field. 

Their on-field performances on Thanksgiving when the Bills visit the Lions and the Cowboys host the Giants can also prove beneficial. Saxx will donate $10,000 to the Testicular Cancer Foundation if Stefon scores a touchdown or Trevon has an interception that day.

“I feel like it works out because we’re the same but we’re completely opposite so it flows together and meshes together,” Trevon says of working with his brother. “It’s really easy — him being who he is and me being who I am. It’s a perfect match.”

With Trevon more focused on football, Stefon has begun to build his off-field portfolio. He was part of Dapper Labs’ $305 million raise in March 2021 and Mad Rabbit Tattoo’s $2 million seed raise that July.

Stefon has talked to his brother about an opportunity to bring an unnamed food franchise to Buffalo. He also has no hesitations about involving Trevon and/or bringing him on as a franchisee himself. Stefon also confirmed it’s “on the table” for him to have some ownership in an unnamed soccer team.

While Stefon may be further along in his career, that doesn’t mean big brother has all the answers. He continually reaches out to Trevon for his thoughts on deals and ideas.

“Tre always has a lot of useful information — random facts sometimes, real Snapple facts like — but it helps me a lot,” Stefon said. “I can ask him a question, even if I have some ideas if something would work or not because part of being a consumer is you have to ask consumers. Bouncing ideas off him always keeps me in a good mind-frame. It’s like a collective decision rather than me going out on a whim saying, ‘I got it, I’ll figure it out.’ I got some assistance.”

It’s how it’s always been for them.

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