After retiring from the NBA, Jay Williams has worked as an analyst for ESPN. Just last year, he announced he would stay with ESPN, despite the layoff turmoil. Even though it’s not clear what will be his new role but fans were excited about the return. However, William’s recent revelation on how the company forced him to hide his business ventures from his own workplace and how they put William in a negative light might not be liked by ESPN itself.

In a recent appearance on the Bloomberg Originals podcast, Williams discussed the pivotal changes he made after a devastating accident ended his basketball career. He recalled a conversation with his late mother, who questioned why his attempts to expand into business had such a negative undertone. His response? “That was always because of ESPN.” He founded a company, Clandestine Ventures, but felt pressured to keep it under wraps.

If you’re wondering what all the secrecy was about, the Duke alum has an answer. “I couldn’t let ESPN know about investing. I couldn’t let ESPN, I, you know, invested in a procurement company for sponsorships because it always got used against me. Like I wasn’t, you know, wasn’t focused on my craft,” Williams shared on the podcast.

The turbulence didn’t stop there. In June 2023, ESPN canceled Keyshawn, JWill & Max show, following major layoffs. While his co-hosts were let go, Williams remained. Reflecting on the situation, he said, “It stinks…the only way I know how to handle things is to play through.”

However, ESPN isn’t the only piece of Williams’ career. Outside of his analyst role, he has a portfolio of ventures. He co-founded Simatree, a management consulting firm, owns part of The CabinNYC restaurant, and advises a digital marketing agency. Partnering with EPIC Insurance, Williams also provides financial guidance to athletes and celebrities. His business success has led to an impressive net worth of $100 million, according to Forbes.

Jay Williams felt trapped in the current media industry operations

Last year, as Jay Williams neared the end of his ESPN contract, he couldn’t hide his frustration. The network was undergoing massive cutbacks, and the former Chicago Bulls player wasn’t happy with the company’s direction. Speaking on the Pat Bev Podcast with Rone, he revealed how working in the current media landscape left him feeling stifled and unable to truly be himself.

“You can never really be your fuc*** self,” Williams admitted. He didn’t stop there, calling out the whole hot-take culture that dominates sports media. “I get how the media industry works… but sometimes that game gets boring to me, dog,” he shared, expressing how the constant need for sensationalism wears on him, even if it feeds social media and headlines.

Williams has been with ESPN for years, starting full-time in 2008. From College GameDay to prime-time game analysis, he became a fixture on the network’s college basketball coverage. He even called the highly watched ESPNU ACC Sunday Night Basketball series, solidifying his role as a go-to analyst.

But before his ESPN days, Williams got his start in 2007 as an analyst for CBS College Sports Network, covering the NCAA Men’s Basketball Tournament. He also had stints with Fox Sports Radio, slowly building his media career before landing at ESPN. Yet now, it seems even this seasoned media personality is fed up with the network’s limiting culture.