Brad Pitt and Jennifer Aniston founded Plan B Entertainment in 2001, just months after their marriage (along with super-producer Brad Grey, who would go on to run Paramount for over a decade). When they divorced in 2005, Pitt kept Plan B, and ever since he and Dede Gardner, along with Jeremy Kleiner, built Plan B into one of the more prestige production houses in Hollywood. It’s not quite A24-level, with a fanbase all its own, but Plan B is a consistent player come Oscar season, and they are known for producing an interesting array of projects beyond Pitt’s own oeuvre, including Kick Ass, Moonlight, If Beale Street Could Talk, Okja, Beautiful Boy, and The Last Black Man in San Francisco. What they don’t do is consistently produce box office successes, but most Plan B films are made with a sub-$100 million budget, so their financial record is less troubling than, say, Annapurna, the production company that billionaire dad Larry Ellison had to bail out. All of this is relevant because Plan B is for sale.


Once upon a time, a man pointed at the gate to his neighbor’s house in Bel Air and said, That house is for sale. Just you watch, Nic is in trouble. Months later, Nicolas Cage’s Bel Air mansion hit the open market, followed by houses in Las Vegas and New Orleans, among other properties Cage owned around the world. This was the 2000s, when Cage had blown through his fortune and landed in tax trouble. The lesson: when celebrities start dumping real estate, follow the headlines and you’ll probably find money problems. That was what got me into following celebrity real estate in the first place, it’s a great warning sign for celebrities in hot water. Another warning sign is when celebrities start selling off business assets, like, oh, production companies.

Of course, it’s not always doom and gloom. Rande Gerber, Mike Meldman, and George Clooney built up Casamigos Tequila and sold it for $1 billion. Ryan Reynolds put Aviation Gin into every movie he made until he was able to sell it for $335 million. And just last year, Reese Witherspoon sold book-to-film pipeline Hello Sunshine to the investment group Blackstone for $900 million. So, celebrities selling their companies isn’t always a red flag. You have to look at the context. Is the celebrity involved in any kind of legal difficulty? Are they losing money anywhere else? No? Then it’s probably okay. But if other factors, such as ongoing lawsuits, or notable financial losses in another investment, do exist, consider the sale of a celebrity business asset a yellow flag. It’s not the end of the world, but it might be a sign of the times. (If they follow the sale of a business asset with the sale of real estate, Danger Will Robinson.)


This why the announcement that Plan B is looking for a buyer and/or new investors caught my eye yesterday. Brad Pitt has all the ancillary indicators of financial distress—multiple ongoing lawsuits, entering year seven of an “only the lawyers get rich” divorce, the lawsuit between Tenute del Mondo and Pitt specifically cites Pitt for mismanagement of the winery, and Pitt just poured an untold sum into renovating Chateau Miraval’s recording studio, which is surely art-friendly of him but probably not the best financial decision, given his partners in the estate are suing him over mismanagement. 

Also, it kind of looks like Pitt is looking for new revenue streams, such as the pending Miraval-inspired NFTs, and his new luxury skincare line, Le Domaine, which just launched earlier this month. Model turned medical esthetician Cassandra Bankson dubbed Le Domaine a “celebrity cash grab” as you’re basically paying for the Pitt affiliation and fancy packaging, the active ingredients are available elsewhere for cheaper.


Selling Plan B, then, is a way to generate cash relatively quickly. I’m not saying Brad Pitt is broke—there isn’t a for sale sign outside any of his properties (yet)—but maybe he’s having a cash flow problem. Maybe he’s not very liquid very right now, and maybe he needs cash for stuff like lawyer fees (which must be intergalactic, at this point), or, perhaps, to shore up his side of Chateau Miraval, which is under scrutiny. (Note: the Make It Right Nola lawsuit settlement is underwritten by Global Green, so Pitt is off the hook for those funds.) I’m just saying, I learned a long time ago to pay attention to when and what celebrities put up for sale. Plan B is for sale. Maybe keep an eye on the real estate blogs to see what happens next.