Mark Walter’s sports empire may be in trouble. We’re not saying he’s guilty of any wrongdoing under federal scrutiny, but the sequence of events is certainly raising eyebrows. From his electronic devices being seized to selling the Los Angeles Lakers within a year to an arm of the Dodgers’ business, which was also dragged into the investigation, a sports analyst now believes Walter’s asset-selling spree may have only just begun.

“It’s starting to seem like he actually might go to jail,” Bill Simmons said on his podcast. “He’s already shed himself of the Lakers. He’s selling his Chelsea stake, which is reportedly 12.5%. And my guess is the Dodgers are going to be next. So what is this? Are we moving towards a Bernie Madoff/Ivan Boesky type situation? Will the words ‘Mark Walter plead guilty’ be said in the next two years?”

Simmons briefly referred to Bernie Madoff, who ran the largest Ponzi scheme in history (valued up to $65 billion) through a fake investment advisory business, and Ivan Boesky, who was caught in a massive insider trading ring in the 80s…

Now, let’s try to understand how and why this connects to Walter.

Earlier this month, Walter suddenly agreed to sell the Lakers for a record $12.5 billion after acquiring controlling ownership of the team for a reported $10 billion valuation roughly 10 months earlier. Because of that, his entire sports empire is suddenly facing a much bigger spotlight.

Walter’s portfolio stretches well beyond the Lakers. He is the majority owner of the Dodgers, valued at about $8 billion in CNBC’s latest valuation, and the Sparks of the WNBA. He also has a minority stake in Chelsea FC, which controls RC Strasbourg, while TWG Global holds a majority stake in the Cadillac F1 team.

Now, Walter and Todd Boehly are also willing to sell their stakes in Chelsea to Clearlake Capital, according to ESPN. Clearlake currently owns 61.5% of the Premier League club, while Walter and Boehly each hold roughly 12.83%. And crucially, Clearlake is willing to increase its stake should the opportunity arise.

That has made Simmons wonder whether the Dodgers could eventually be next. Walter’s group has overseen an aggressive spending era in LA, with the Dodgers winning consecutive World Series titles in 2024 and 2025. Simmons believes that spending $2.15 billion to buy the Dodgers, and hundreds of millions more in development over the years, makes them an important piece of Walter’s story.

“If he has to sell the Dodgers, who spent so much money over the last seven years that they are single-handedly creating the baseball lockout next year,” Simmons predicted. “The Dodgers are back-to-back champions partly because of all the f*****g money this guy spent.”

For now, though, there is no confirmation that Walter plans to sell the Dodgers. However, a recent report has dragged the MLB franchise into the potential financial improprieties situation…

“Delaware Life revised its disclosures to identify nearly $17 billion more in investments tied to related businesses, increasing its share of the company’s portfolio from about 3% to 42%,” Alex Andrejev, Melody Gutierrez and Rebecca Tauber reported for The Athletic.

“One of the investments that appears to be caught up in the reclassified dealings was a $4.1 million loan to Dodger Tickets LLC, a subsidiary tied to the Dodgers and involved with ticketing and other business operations. Delaware Life listed that loan as unaffiliated in its 2025 annual statement. In the March filing, the same investment was listed as affiliated.”

Why does this matter? Federal prosecutors and the SEC are investigating financial dealings involving two Delaware insurers controlled by Walter. After internal reviews, the insurers reclassified about $21 billion in investments as related-party assets, raising questions about whether those relationships were properly disclosed to regulators.

Some of the loans were made to companies also tied to Walter. The concern is whether the transactions created conflicts of interest that should have been reported initially.

Walter and TWG Global have denied wrongdoing. The company has said Walter and his businesses have acted in good faith and are cooperating with authorities.

Now, there is also no public confirmation that the Lakers sale was prompted by the federal investigation, although recent reporting has linked the sale to Walter’s broader efforts to raise liquidity and pay off debts amid the financial scrutiny.

The investigation into Walter and his companies began last year, with the FBI even seizing phones and computers from Walter and a top Guggenheim Investments executive as well. Crucially, at the time, he hadn’t taken over the Lakers yet. The NBA Board of Governors was yet to approve the move. But six weeks later in October, they did, and the LA franchise was handed over to Walter.

The Lakers then went on to have a decent regular season, but their playoff hopes were cut short in the second round. In the background, Walter and Jeanie Buss had already begun the ‘Dodgerfication’ process, laying off staff from the earlier ownership to transform the franchise into an analytics-driven strategy.

Walter even transitioned major Dodgers names like Lon Rosen from the MLB to the NBA franchise to help transform the front office. The Purple and Gold even went all out to bring in new players like Walker Kessler, Quentin Grimes, Sandro Mamukelashvili, and a lot more. The pivot this franchise was making was visible.

However, all of a sudden, new buyers, Josh Kushner and Bob Iger, showed up last week and put together a $12.5 billion deal to purchase the Lakers. And just like that… Walter’s reign was over within a year. What’s more surprising is that Iger later revealed the takeover conversations with Walter took only three days!

Crucially, the NBA Board of Governors has yet to approve the deal.

On the other hand, no charges have been filed against Mark Walter. He has also declined to answer questions about the Lakers sale and the exact reason behind it.

The timing has fueled speculation about what could come next…