Almost exactly 365 days after selling his first-ever shares of JPMorgan stock since becoming CEO in 2005 (back when Brad Pitt and Angelina Jolie were playing house in Mr. and Mrs. Smith), Jamie Dimon is back at it. The final bank boss just sold 866,361 shares at $269.83 per share, for $233.77 million.

Ironically, the sale came right as JPMorgan’s stock hit an all-time high of $278 before promptly dipping to $266 post-sale (coincidence? Probably not).

This isn’t some one-off move. Last February, Dimon dipped his toes into the selling pool for the first time ever, then went for round two in April, cashing out $182 million in 2024 alone. Add in this latest $233M sale, and the guy has now pulled in over $415 million in stock sales in just a year. (I guess yachts don’t buy themselves.)

JPMorgan’s official stance was for “Financial diversification and tax-planning purposes.” But my translation of that is: “I swear I still believe in JPM, but I also like having options.” The filing insists Dimon still sees “strong prospects” for the company and is keeping a “significant stake”... but if you just bought a bunch of JPM at all time highs and were hoping for an “I’m all-in” moment, you’re fresh out of luck.

Dimon has a spooky sense for JPMorgan’s stock movements. Back in 2016, when the market was in freefall, he bought $25M worth of JPM stock, calling the exact bottom of the market and essentially willing a rally into existence. Now he’s selling at record highs and has been reluctant to approve share buybacks at these levels. His words on CNBC: “You should buy back the stock when you think it’s cheap… we have been very reluctant to buy back stock at these prices.”

While JPMorgan has jumped 41% in the past year, some analysts are wondering if the stock has peaked. It recently led the KBW Bank Index lower, dropping after Dimon’s scorched earth approach to remote work made headlines.

And speaking of that… Part of the reason Dimon’s stock sale is getting less attention is because he’s also cussing out his own employees.

A leaked recording from a JPMorgan town hall meeting caught him going full angry dad mode, saying, “Don’t give me the s!@# that ‘work from home Friday’ works.”** And when employees started a petition to keep hybrid work? Dimon’s response: “I don’t care how many people sign that f*ing petition.” (Employee morale must be soaring.) He later walked back the cursing but doubled down on the message: “We’re not going to change. We’re going back to the office.”

As far as business moves… JPMorgan is wading pretty far into the private credit deep end, setting aside $50 billion to lend directly to companies outside traditional markets. This is part of a broader trend where banks are stepping into territory usually dominated by hedge funds and private lenders. (regular banking just isn’t exciting enough anymore.)

This could be a huge money-making play long term, but it also cranks up the risk. Some are speculating that Dimon’s eventual departure might be his way of sidestepping any future migraines if this investment on private credit goes sideways.

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Stock.News does not have positions in companies mentioned.