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You don’t have to be an fan to recognize . Indeed, Sir Charles doesn’t need the pretext of a ring to be the people’s champion: Between his past as an athlete, his present titles of entertainer, ad man du jour and an indespensible ingredient within TNT’s award-winning Inside the NBA — he is as likable as he is brutally honest.


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When pressed on the differences a young Barkley received off the court compared to today’s professional athlete, during a recent sit down with Entrepreneur, the always-forward former forward bristled at the lack of focus with many talented pros.

“Guys, you’re already making so much money playing ; you don’t have to jump at every dime that comes your way,” notes the Leeds, Alabama native. “Do you want to be the best basketball player you can be?”

Barkley insists that there are exemplars among today’s pros, (citing and Kevin Durant as two notables) who do a lot outside of the sport, but their respective number one focus is always basketball.

While Chuck is quick to heap praise on a career that keeps on giving, (he was filming Subway commercials prior to this interview) the “Round Mound of Rebound” was also quick to think more broadly about the difference his economic advantages can have on those less fortunate and is famous for contributing over $1 million on an annual basis to charities.

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From the pick-and-roll to picking your role

The question of how he handles the word “no” brought back a conversation he had with Hall of Famer, Julius Erving, during his early playing days.

“Dr. J was like, yo man, you do know you play basketball for a living?”, recalls Barkley “We don’t have to do every charity event. There are millions of charities and they gonna keep coming. You don’t have to feel bad about saying no.”

That conversation stuck with Chuck: “The ‘word’ no is a very important part of your repertoire.”

Barkley has been propositioned to put his name and likeness across brands from around the world. Historically the answer has been a flat “no”.

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Business as a home game

“I had been looking to own a business in Alabama for the last 15 years,” notes the Auburn University legend. “The opportunity to be a part of Redmont Distillery was intriguing.”

Like a seasoned vet, he wanted to understand the value proposition before jumping into the spirit’s game.

“My first thing was, is this product any good? So, I got several of my guys together, and we love to drink,” says the entrepreneur of how he settled on his clean, smooth finish and 8x distilled offering. “So I said, ‘Guys, let’s figure out how we like to drink .'”

If the team thought Barkley would passively participate from the sidelines, they quickly figured out that the infectious Charles charm only goes so far.

“I bought it, then the team said, we’re going to sell Redmont Vodka in this state and that state,” says Charles of his leadership style. “I said, ‘take a step back — why are we spending money when we aren’t making money? We aren’t just going to run through my money.'”

The former player had a plan: The state was his strategy. He knew Auburn fans would support his venture and, frankly, all of Alabama.

“I started [giving] to my high school, then college, and then a couple of inner-city schools in Birmingham,” notes Charles of why Alabama has been very good to the team at Redmont. “Eventually, I gave back to HBCU’s and Wounded Warriors because the greatest country in the world treats their soldiers like shit.”

This means something to Charles. He isn’t in it for the competition of selling to the highest bidder like many of his contemporary celebrity spirit ventures.

“I know a lot of these guys that have their own alcohol companies, but they just have their name on the bottle,” declares the distiller. “I own my company and it’s in Alabama — that’s what matters to me.”

A whole new ballgame

Now that Charles has confidence in his Redmont team and they with him, a new partnership with ReserveBar positions Redmont Vodka to be celebrated by consumers across the country.

The famed or infamous Nike commercial pitting Charles as the anti-role model figure in 1993 still holds water for the gentle giant.

“I haven’t changed my opinion, I don’t want role models to be people kids never even know, they should be in their homes,” states Barkley. “Kids thinking that they are going to be in the NBA or the NFL because of professional athletes is wrong, those kids are probably going to have to get a real job.”

Even as Charles politely bristles at the ‘role model’ talk, he can’t walk away from opportunities that lean into role model status. The World Games are taking place in Birmingham and Sir Charles is serving as the honorary co-chair and ambassador for the event and, of course, he’s bringing Redmont Vodka along for the ride as a premier partner.

“Man, I’m excited about the World Games because it is about Birmingham,” says Chuck. “It’s going to be great for the city.”

Does Sir Charles have a blind spot, and if so, how close to the vest would he play his hand?

“I was planning on retiring at 60 and I’m 59, now,” he says of his TNT gig. “Somebody screwed up my contract, so the original plan has turned into a couple more years. I’m a grandfather and being there for the birth of my grandson, Henry, and being with my daughter on her first Mother’s Day? Man, it’s crazy.”

The late John Madden, Hall of Fame NFL coach and broadcaster, knew when to walk away on top and Charles is deciding when he can invoke a similar Madden “boom” on a career well-lived.

“I don’t want to die on the vine. Madden did it right,” says Barkley. “He went out on top. I want people to say of me, ‘That dude, that guy is a legend.'”

Charles prefers his Redmont Vodka with club soda, a splash of cranberry juice and a lime. Here’s a hunch: Barkley doesn’t give a damn how you like it — just that you like it.

Related: 20 Celebrities Who Started Alcohol Companies

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