In July, S&P 500 companies announced $166 billion in stock buybacks — the biggest July on record. That’s the corporate treasury spending shareholder money to hoover up its own shares and tell everyone the stock is a bargain too good to pass up. So here’s the number they’d rather not put in the same sentence: the executives signing off on those buybacks sold $77.6 billion of their own stock in the first half of the year, the second-fastest insider selling pace in more than two decades. With their own cash, those same insiders bought back $6.9 billion. They sold roughly eleven dollars of stock for every one they were willing to buy.
If the shares were the steal the buyback is pretending they are, the people who know the company best would be backing up the truck, not sprinting for the exit. A buyback isn’t a vote of confidence — it’s a bid. A giant standing order that soaks up shares and holds the price up. And the most convenient thing in the world to do with a price that’s being propped up on the company’s dime is sell into it. That’s the whole trick. The treasury manufactures a buyer, the boss becomes the seller, and the paperwork calls it “returning capital to shareholders.” One shareholder in particular.
Now remember whose money that is. Every dollar spent holding the stock steady so an executive can cash out is a dollar that didn’t go to the workers cut loose “for agility,” or to the raise nobody in the building saw this year. The buyback was never for you, and it was never for some patient long-term investor either. It was the getaway car. The people with the most inside knowledge are quietly betting against the thing they run — with their own paychecks — and using the company’s cash to hold the door open while they climb out.