The REAL Reason Trump is Invading Iran 
These 3 Stocks Are Drawing Insider Buyers for Very Different ReasonsWritten by Leo Miller on September 18, 2026 
Key Points
- Uber CEO Dara Khosrowshahi and COO Andrew Macdonald bought a combined $15.3 million in shares despite the stock falling over 10% in 2026.
- GameStop directors and CEO Ryan Cohen purchased more than $21 million in shares even as quarterly sales declined nearly 19% year-over-year.
- Welltower has seen no insider selling in 12 months, and a director increased his stake by 33%, signaling confidence despite strong recent gains.
- Special Report: The energy story near the Grand Canyon
Insiders are buying some of the best-known stocks in transportation, retail, and real estate. These buys come amid different backdrops for each firm and stock. A top ride-hailing company is seeing considerable insider buying, with shares down in 2026. Meanwhile, insiders continue to increase their stake in a former meme stock, even as sales are under real pressure. Additionally, following very strong gains, insiders at a top real estate investment trust continue to hold or increase their positions, indicating long-term confidence.
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Top Uber Executives Are Purchasing Amid Underwhelming 2026 PerformanceAfter an impressive 2025, Uber Technologies’ (NYSE: UBER) share price has run into some roadblocks. Shares gained more than 35% last year, but are down more than 10% this year and have fallen more than 25% from their 52-week high. Notably, the stock fell more than 5% after Uber’s last earnings report. The company missed on revenue, with sales rising 12% year-over-year to $14.19 billion versus estimates of $14.24 billion. Additionally, its bookings guidance for the next quarter fell short of expectations. Uber also said it would commit over $10 billion to autonomous vehicle (AV) investments. While this could bode well for Uber’s cost structure long-term, it also implies significant upfront costs. Amid its lackluster performance recently, two key insiders are buying in. CEO Dara Khosrowshahi and Chief Operating Officer Andrew Macdonald have purchased $10 million and $5.3 million of Uber shares, respectively. Khosrowshahi’s shares increased by approximately 11% while Macdonald’s increased by approximately 20%, equating to significant buys for these insiders. Top insiders are clearly signaling confidence in Uber’s outlook going forward, while the relative lack of recent insider selling indicates a constructive outlook among other insiders. From Q4 2025 to Q3 2026, Uber’s total insider selling was less than $6 million, compared to insider buying of $16.6 million. GameStop Insider Buys Are Up, Sales Are DownShares of GameStop (NYSE: GME), one of the original meme stocks, have been on a bit of a roller coaster recently. Shares sank nearly 26% in 2025, but went on to rise as much as 32% earlier in 2026. However, the stock is now up by less than 10% on the year. Shares cratered by more than 12% after GameStop said it would exchange $1.4 billion worth of convertible notes for its common stock, a dilutive event. The company subsequently amended this, saying it would pay $358.4 million of this consideration in cash, helping shares rebound. The stock also got a boost after its latest earnings report, with sales of $790.2 million beating estimates of $756.85 million. Several insiders bought shares following GameStop’s better-than-expected report. Together, directors Alain Attal, Lawrence Cheng, and CEO Ryan Cohen bought over $21 million worth of shares. Attal and Cohen’s additions increased their positions by less than 1% and less than 3%, respectively. However, Cheng’s position increased by more than 60%. While these buys indicate confidence in the firm’s outlook, the company’s sales are still in decline, falling nearly 19% last quarter. This, combined with its scattershot strategy, demonstrated by its attempt to purchase eBay (NASDAQ: EBAY) for $55 billion, continues to be a significant concern.
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Welltower Insider Trading Points to Durable OutlookLast up is real estate investment trust giant Welltower (NYSE: WELL). The stock provided a return of nearly 50% in 2025, and it has continued to perform strongly in 2026, up more than 20%. Welltower’s success comes as it provides rental housing for senior citizens, an industry with significant structural tailwinds. As the percentage of U.S. residents who are in higher age brackets increases over time, Welltower’s senior housing is seeing strong demand. Welltower’s insider trading data may signal the durability of this trend. Notably, MarketBeat has tracked no insider selling at Welltower over the last 12 months. At the same time, director Andrew Gundlach recently purchased over $2.4 million worth of Welltower shares. This marked a substantial 33% increase in Gundlach’s position, boosting his shares held from 20,000 to 30,000. These are positive signals for Welltower stock. Despite its very strong performance, insiders are not selling. In contrast, Gundlach provides an example of an insider greatly increasing their allocation. One way to read this is that insiders are confident in continuing to hold this name because demographic aging is a long-term trend. From 2025 to 2060, the U.S. Census Bureau projects that the percentage of the U.S. population that is 65 or older will rise from 18.9% to 23.4%. Analysts Point to Strong Gains at Uber, Watch AV Profitability ImpactsLooking ahead, analysts are eyeing the most 12-month upside in Uber among this group. The MarketBeat consensus price target near $103 implies more than 40% upside in shares. A key watch item will be how Uber’s AV strategy affects profitability over time. Specifically, seeing improvements in its mobility operating margin, which was 7.6% last quarter, would help signal that autonomous deployments are boosting profitability rather than deteriorating it. However, this may take time to materialize as the initiative ramps. Read this article online › Recommended Stories
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