John Henson Confirms Retirement, Thrilled About Next Career Phase in Sports Media

That summer, the Bucks wound up winning their first NBA championship in over 50 years.

“It was like a closing chapter for me,” Henson said of Milwaukee’s title win. “When they were trying to win it, I almost had anxiety like, 'Oh man, are they gonna win? What's gonna happen? Hopefully they win.' And then, part of you's like, 'Ah, they traded me. I don't want them to win.' But when they did win, I was just happy for 'em. I love it for them. We’re still close to this day.”

The Bucks selected Henson with the No. 14 in the 2012 NBA Draft. One year later, Milwaukee took a chance on an international prospect named Giannis Antetokounmpo; Henson’s draft classmate Khris Middleton joined the two via offseason trade from Detroit as well.

Henson remembers Antetokounmpo getting off the plane in Milwaukee and being one of the first people that the “Greek Freak” saw in his new home. He’ll also never forget training in Houston with Middleton, who was fighting just to get to the league at the time pre-draft.

“I'm over there, lottery pick, not traveling, working out every day smiling,” Henson said. “He's all like, 'I'm going to this workout.' He's working out for 30 teams. I was driving the big Inifiniti, he had the humble Explorer from [Texas] A&M. I've seen those guys grow, man, so I'm so happy for those two specifically 'cause I've seen where they came from and the amount of growth as people and their bank accounts.  

Still great friends with his old teammates and Middleton, Henson foresees the recently turned 33-year-old getting another big payday and Milwaukee making plenty of noise in the 2024-25 season.

“He's getting older, but he's still got some kick left in him. The Bucks need him really bad. I think they're gonna be a lot better than people think this year. They're kinda hiding under the radar right now. No one's really talked about them.  

“That's how they want it. That's how Khris likes it. That's how the Bucks want it – flying under the radar and all of a sudden you look up, 'Hey, we're No. 1 in the East and we just won a championship.' They're not sneaking up on anybody this year, but I think the noise is a little too quiet around 'em. People should start kinda looking at 'em.”

Henson maintains a great relationship with the Bucks. General manager Jon Horst calls him frequently to check in and let him know that the door is always open for a front office role or to work in a scouting capacity.

That’s just one opportunity that’s popped up. Since his NBA days concluded, Henson has entertained a couple of different propositions. For example, the G League Ignite asked him to be the team’s veteran big. The Washington Wizards also inquired about him being a front-bench assistant coach for their G League affiliate, the Capital City Go-Go, and a player development associate for the NBA team itself.

But as the years passed, Henson wanted to go in a different direction. One night, at a country music concert, he met a fan named Max, who connected with him based on a mutual interest in NFTs and Bitcoin. Max’s roommate turned out to be a sports media agent, so everybody put their heads together and Henson started podcasting.

The agent was well-connected and persuaded Henson to interview for a basketball talent position on a sports betting show on MSG Network called The Bettor Half Hour. It went so well that he started the next day. Henson was an office employee with a scan card and co-workers, all of whom he is grateful for.  

“MSG's a pretty popular network with the Knicks, so that was super helpful with me 'cause we were live, first of all,” said Henson, who lived in New York for back-to-back summers at a temporary residence. “So I'm on live TV three months removed from my career, I have no idea what I'm doing – butterflies, I'm sweating. Obviously it became second nature and the people there helped me out.

“So I did two seasons with them and that's kinda when everything blossomed – college basketball and the other opportunities that I've done, and it's been fun. It's a challenge, it's been fun, it's been a new journey. It's kinda exciting because you just never know who's gonna call or who needs you.”

A beloved alum of the University of North Carolina, Henson feels his college career has afforded him the majority of his opportunities in the media space.  

He was a shot-blocking savant and a rebounding machine at Chapel Hill, earning ACC Defensive Player of the Year, ACC All-Defense and All-ACC honors twice each.  All of that success came under legendary Hall of Fame head coach Roy Williams before the NIL era.

“I laugh all the time. I stayed in school for free, so imagine having NIL. It's great to see them getting paid,” Henson said. “But it was a great experience man. I loved every minute there. It was the best time of my life to this day. Not even close.

“I still talk to a lot of teammates. Harrison [Barnes] is my guy. I talk to him all the time. He's down in San Antonio, so that'll be fun. I said, 'Look man, Wemby [Victor Wembanyama] might be able to get you another deal man!' So he's gonna be excited about playing down there.”

Henson’s time with the Tar Heels was memorable from start to finish, but one time period stands out in particular. After a not-so-successful freshman campaign where North Carolina went to the NIT, nobody expected the team to compete much in the 2010-11 season.  

Freshman like Barnes, Kendall Marshall and Reggie Bullock were coming in. Henson’s fellow sophomores, Dexter Strickland and Leslie McDonald, had to step up. Aside from Tyler Zeller, Larry Drew and Justin Knox, the juniors who played consistently, upperclassmen played more of a leadership role than being the brunt of the Tar Heels’ production.

In spite of all that, North Carolina won the ACC.

“Because I'm doing sports betting nowadays, the odds had to have been plus-thousands. You probably could've put a hundred bucks on us and won three, four-grand, 30-grand, whatever,” Henson said. “That was probably the best feeling in the world. No one believing that you guys would be anywhere near and then ultimately winning the ACC Championship. We were projected I think out of the top seven.”

These days, the Tar Heels are in the midst of a new era headed by Hubert Davis. The 1992 first-round NBA Draft pick and former North Carolina standout took over for his alma mater following Williams’ retirement in 2021.

In three years, the Tar Heels have a 78-31 record with two NCAA Tournament appearances under his wing. That includes a runner-up result in the NCAA men’s title as an eighth seed against the Kansas Jayhawks in his first season at the helm. And despite falling in the Sweet Sixteen this past April, North Carolina won the ACC and earned a top seed in the Big Dance.

“He was kinda grooming for that job as well when he was under Coach Williams, and I'm sure he kinda knew that he might be the next guy. The pressure of coming after Roy Williams, nobody wants that pressure, and he took it on. And for the most part, he's doing well. He's been to a Final Four, was up at the halftime of a championship game, so I'm happy for him.”

Asked whether or not he’s keeping the door open to a comeback on the court, Henson had a funny response.

“I’m done bro lol,” Henson texted RG.org with an old-man emoji in clarification. “I was so blessed to play this long. It's a lot of opportunities, man. It's just a matter of one step at a time. I'm only 33, so I have time to explore and figure out what I want to do next. This is just the next phase, and we'll see where it takes me. But so far, so good.  

“Year 3 out of the NBA, being able to do all these things [with] all these companies and have all this interest kinda drummed up, I'm thankful.”