Throughout his 11-year NFL career, Ricky Williams thinks he would have been drug tested at least 500 times. Here’s the crazy part: He played in 147 games throughout his NFL career and recorded 342 receptions. That means he was tested way more times than he even caught the football! Known for his association with cannabis, he even stated in 2016 that he “might have the world record for most times drug tested.” Things had reached a point where the drug testers became like family to them, which could have helped the athlete get away.

“The one test where he got caught that had him suspended for the four months, we could have switched it that day if we wanted to,” Williams’ wife Kristen once revealed. “That guy, we knew him so well … he tested Ricky and left them both [samples] sitting on the counter and left for 45 minutes and then came back.” But Williams wanted to be honest.

By the 2004 season, he failed a drug test for the third time and was suspended for the entire 2006 season after failing a fourth test. 2007 witnessed something similar, which led to multiple tests per week, as Williams applied for reinstatement. All this led to him missing 36 games and losing up to $10 million in potential earnings throughout his NFL career. But it seems Ricky Williams turned this failure into a flourishing business.

Per Taylor Webb, co-host of Pocket Presence with Kurt Benkert, Williams didn’t start smoking regularly until college. Apparently, he had the worst game in his career up until that point. Which game? It was in 1998 when Texas had just come off a 43-7 loss to Kansas State, and Ricky’s stats were as underwhelming as it can get: 25 Att, 43 Yds, 0 TD. Handling such a career-low left him second-guessing his decision to return for his senior year.

But when his roommate suggested something that would help him ‘chill’, he tried out the substance to realize it helped him not obsess over his failures. But just within the next two weeks, he became the 1998 Heisman winner.

As reported by Webb on X, “Today, Ricky owns a cannabis brand of his own called @Highsman34, where he sells products in 10 different states. He calls the money he lost in the NFL “pennies” compared to the profits his cannabis investments will generate.“

He continued smoking, but when he got traded to the Dolphins in 2002, he failed his first test, but that didn’t make him stop. A number of failed drug tests emerged over the years and when he retired in 2012, one would have thought he lost his prime to the substance. But Williams doesn’t see it that way.

In 2015, when an old teammate approached him to speak at a cannabis conference at Phoenix, Williams first declined the opportunity. But eventually, he felt he needed to share his story. “As I told my story, any share that I had just left,” Williams told Webb. Fast forward to today, he owns a cannabis brand.

In September, reflecting on his time in the league, he stated, “Everything I went through, all the trouble I got into, I still got into College Football Hall of Fame, still got a statue at Texas, they still named the field after me. So showing people, if you stick to your guns and trust who you are, everything will work out fine.” His transition from football to entrepreneurship proved lucrative, and over time, his company has raised $3.5 million in funding.

Today, Williams stands as a testament to reinvention. From facing harsh NFL penalties to becoming a successful cannabis mogul, he has transformed his narrative from one of lost opportunities to one of empowerment and success. “I need to find something else,” he once said, pointing to his gradual disillusionment with football. And he certainly did.

Ricky Williams: Elevating with a new cannabis brand

Ricky Williams is breaking fresh ground with his new venture, Highsman — a cannabis lifestyle brand that goes beyond just the product. Williams credited cannabis for helping him manage the intense physical and mental demands of professional football. In July, he stated, “Having cannabis in my life helped me appreciate, enjoy, and recover from the brutal game.”

With Highsman, Williams isn’t just selling cannabis; he’s selling a lifestyle—one not fit for everyone. “We’re selling a lifestyle,” he explained. Highsman includes cannabis products for everyday wellness, with fans nationwide supporting the brand as it lands in stores and dispensaries.

Williams’ motivation for this business is personal. Cannabis, he believes, isn’t just about relaxation; it’s an integral part of a healthy, high-performance life. Highsman is gaining traction across the U.S., with an aim to reshape how athletes and everyday people view cannabis.

He’s also teaming up with other cannabis entrepreneurs like Chris Ball, sharing a vision to build a community of wellness advocates who understand cannabis’ potential. Williams’ mission? Change the stigma and “Spark Greatness” for those looking to benefit from responsible cannabis use. With Highsman, he’s taking his legacy beyond the field and into a new era of wellness.