When insiders invest millions of dollars of their own money in company stock, investors tend to pay attention. After all, executives and directors already have plenty of exposure to their businesses. So, when they voluntarily reach into their own pockets and purchase shares on the open market, it can be a powerful vote of confidence.
That is exactly what recently happened for three struggling stocks: GameStop (NYSE: GME), Uber Technologies (NYSE: UBER), and Dick’s Sporting Goods NYSE: DKS).
Ryan Cohen Makes Another Big Bet on GameStop
GameStop Corp. has gone from a leader among meme stocks to one of the struggling stocks in 2026. However, CEO Ryan Cohen recently spent about $20.4 million to purchase another one million shares of the video game retailer.
According to a filing with the US SEC, Cohen paid between $20.02 and $20.47 per share. It was his first open-market purchase since January, when he bought one million shares for approximately $21.4 million. Cohen was not alone. Directors Lawrence Cheng, James Grube, and Alain Attal purchased a combined 70,255 shares for about $1.3 million. Cheng made the largest investment of the group, picking up 55,000 shares.
Uber’s CEO Bought $10 Million Worth of Stock
Uber Technologies CEO Dara Khosrowshahi picked up about $10 million of his company’s stock.
Khosrowshahi bought 141,000 shares at an average price of $70.96. The transaction increased his total position to about 1.37 million shares, worth roughly $100 million.
What made the purchase particularly interesting was how quickly it was disclosed. Insiders generally have two business days to report their trades, and many wait a day or two. Khosrowshahi’s filing appeared around 12:40 p.m. Eastern on the same day he bought the shares. The market reacted almost immediately. Uber stock jumped approximately 3% after the disclosure and finished the session at $72.56, up 2.1%.
It was Khosrowshahi’s first open-market purchase of Uber shares since May 2022. It also followed another large insider transaction. On September 4, Chief Operating Officer Andrew Macdonald bought 70,000 shares for about $5.3 million, paying between $75.23 and $76.85 per share. Those two purchases send a fairly clear message: Uber’s top executives appear to believe the market is undervaluing the company.
DKS Directors Buy After a 30% Collapse
Insiders also stepped in at Dick’s Sporting Goods after a disappointing earnings report sent the stock plunging 30% in a single session.
The shares fell to approximately $124, their lowest level since 2023 and nearly 50% below the 52-week high of $244 reached in June.
Four directors, including Robert Eddy, Sandeep Mathrani, William Colombo, and Mark Barrenechea, responded by buying up a combined $3.7 million of stock. Barrenechea made the largest investment, buying 17,000 shares.
The purchases came as investors worried about Dick’s $2.5 billion acquisition of Foot Locker. Dick’s reduced its comparable-sales outlook for Foot Locker to a range of negative 2% to flat, down from its previous forecast of 1.5% to 3% growth. Quarterly earnings of $3.53 per share also fell short of the $3.76 analysts expected. Wall Street subsequently cut its 2026 earnings estimates to less than $12 per share from about $14.
Even so, some analysts believe the selloff went too far. Morgan Stanley analyst Simeon Gutman maintained a Buy rating but reduced his price target from $270 to $180. His argument is that the core Dick’s business can generate roughly $12 per share in annual earnings without Foot Locker. That means investors were valuing the core operation at only a little more than 10 times earnings following the plunge.
What Insider Buying Can Mean for Struggling Stocks
Insider buying is never a guarantee that struggling stocks have reached a bottom. Executives can be early, and even the people running a company cannot predict every competitive or economic challenge. However, these transactions are still worth watching.
At GameStop, insiders are expressing confidence, but investors want more proof of a successful turnaround. At Uber, two major executive purchases suggest that management believes fears about autonomous vehicles have created an opportunity. At Dick’s Sporting Goods, directors appear to be betting that the market overreacted to near-term problems involving Foot Locker.
