The 18-times major champion Jack Nicklaus has built one of the most recognizable brands in golf, but he recently admitted that one business decision still haunts him decades later.

Speaking in a recent interview on The Big Swing With Jimmy Roberts, Nicklaus reflected on the sale of the company he founded and described it as the biggest regret of his life.

“I wish I wouldn't have sold my company,” Nicklaus said.

Nicklaus sold the rights to his name, image, and golf course design business (Nicklaus Companies) in a $145 million deal backed by Howard Milstein in 2007.

“But I mean, I've got my company back and we're working with it. And we ended up having a long legal issue on that and then turned out all right.”

The arrangement led to nearly two decades of legal disputes before he regained control of the company in 2026 following bankruptcy proceedings.

Reflecting on the experience, he also shed light on the philosophy that guided his decisions throughout the career.

“I always felt like I wanted to give the other guy a better deal than I got,” Nicklaus said in the interview. “And if I did that, then I could always keep my head up and say, ‘Hey, that was a fair deal.’”

He prioritized fairness in dealings rather than maximizing profits.

However, the story did not end with the sale itself.

Why getting the company back mattered

For Nicklaus, getting the business back was more than ownership. He repeatedly emphasized the importance of family and legacy over financial gain in the same interview.

He explained that the motivation was rooted in ensuring the future of the business remained in family hands.

“I’m not concerned about what I'm interested in is the legacy that I leave my family,” Nicklaus said.

The six-time Masters champion noted that the company now represents the future of his family rather than his own ambitions.

“The business is theirs,” he said while discussing his children and grandchildren. “I really think that they ought to have the opportunity to direct it forward, not somebody from the outside.”

More than a reflection on a business deal, Nicklaus' remarks underscored how he views success at this stage of his life. Rather than focusing on financial gains, he remains committed to building a legacy that can be carried forward by his children and grandchildren.

What do you make of Nicklaus' biggest business regret? Let us know in the comments.

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Written by

Pulkit Prabhav

Edited by

Pulkit Prabhav