For much of the last 17 years, the bulls have been in firm control on Wall Street. However, it's the stock market's largest and most influential companies that are responsible for most of the heavy lifting. I'm talking about the $2 trillion-and-up club, consisting of Nvidia (NVDA 0.53%), Apple (AAPL +1.33%), Alphabet (GOOGL +1.10%)(GOOG +1.09%), Microsoft (MSFT 0.98%), and Amazon (AMZN +1.23%).
Since the benchmark S&P 500 (^GSPC +0.80%) hit its financial crisis low on March 9, 2009, it's rallied 873%, through the closing bell on April 2, 2026. In comparison, Nvidia has skyrocketed more than 85,000%, while Apple, Alphabet, Microsoft, and Amazon are higher by approximately 8,500%, 4,000%, 2,400%, and 6,800% over the same timeline.
Though there's a laundry list of reasons these members of the "Magnificent Seven" are trillion-dollar companies, the people who know these five juggernauts best are sending shockwaves through Wall Street with their actions.
Image source: Getty Images.
Wall Street's most influential businesses are being fueled by AI and sustainable moats
The reason these five companies have outperformed the S&P 500 so decisively over the last 17 years is that they all possess sustainable moats or ironclad competitive advantages:
- Nvidia's graphics processing units (GPUs) hold a virtual monopoly in artificial intelligence (AI) data centers. No external competitors have come close to matching the compute capabilities of Nvidia's GPUs.
- Apple's iPhone continues to be the best-selling smartphone in the U.S. and around the world. Apple's innovation has helped it build a loyal customer base willing to pay a premium for its products and services.
- Alphabet's Google is a veritable monopoly in internet search. According to GlobalStats, Google accounts for approximately 90% of worldwide internet search traffic.
- Microsoft's legacy operating system (OS), Windows, remains the dominant OS globally, while its cloud infrastructure service platform, Azure, is No. 2 in worldwide spend.
- Amazon is a dual-industry leader, with its online marketplace the clear No. 1 in the U.S., and Amazon Web Services (AWS) the leading cloud infrastructure services platform by total spend.
These magnificent businesses are also taking full advantage of the AI revolution. Whereas Nvidia is dominating on the hardware end, Alphabet, Microsoft, and Amazon are enjoying reaccelerating sales growth for their respective cloud infrastructure service platforms, thanks to the incorporation of generative AI and large language model capabilities.
However, the individuals who know these pillars of Wall Street best are sending all the wrong signals to investors.
Image source: Getty Images.
This $16 billion warning shouldn't be swept under the rug
Insiders tend to be their company's biggest cheerleaders. An "insider" is a high-ranking executive, board member, or beneficial owner with at least 10% of a company's outstanding shares.
For the sake of transparency and to comply with rules and regulations set by the Securities and Exchange Commission (SEC), insiders are required to file Form 4 with the SEC within two business days of buying or selling shares of their company. This also includes the exercising of option contracts.
The Form 4 filings for Nvidia, Apple, Alphabet, Microsoft, and Amazon over the trailing two-year period, ending April 2, 2026, show a disturbing trend:
- Nvidia: $4.11 billion in net-selling by insiders
- Apple: $365.1 million in net-selling by insiders
- Alphabet: $401.4 million in net-selling by insiders
- Microsoft: $278.6 million in net-selling by insiders
- Amazon: $10.93 billion in net-selling by insiders
Collectively, almost $16.1 billion more in stock has been sold than purchased by insiders at these esteemed companies over the trailing two years.
NASDAQ: NVDA
Key Data Points
There is a bit of an asterisk to the above selling data. Namely, most executives and board members receive the bulk of their compensation in the form of stock and/or options. Many of these individuals sell a portion of the share-based compensation they receive to cover their federal and/or state tax liability. Tax-based selling isn't bad news for investors.
While there are several reasons for insiders to sell shares of their company, not all of which are inherently nefarious, there's only one reason for insiders to buy shares: the belief they'll head higher. Unfortunately, insiders haven't been opening up their wallets at Wall Street's most influential businesses over the trailing two years:
- Nvidia: $0 insider buying
- Apple: $0 insider buying
- Alphabet: $4.95 million in insider buying
- Microsoft: $3.44 million in insider buying
- Amazon: $0 insider buying
Three of the five largest publicly traded companies haven't seen a single insider buy in over two years, while the other two tallied just $8.4 million, combined. If insiders aren't willing to buy their own company's stock, it sends the message that they don't believe it's a good value.
S&P 500 Shiller PE Ratio hits 2nd highest level in history 🚨 The highest was the Dot Com Bubble 🤯 pic.twitter.com/Lx634H7xKa
-- Barchart (@Barchart) December 28, 2025
Keep in mind that the stock market entered 2026 at its second-priciest valuation over 155 years, according to the Shiller Price-to-Earnings Ratio. The two previous times when the Shiller P/E surpassed 40 -- the dot-com bubble and the first week of January 2022 -- were followed by declines of 49% and 25%, respectively, in the benchmark S&P 500.
Individually, Apple is historically pricey, based on its trailing 12-month earnings per share, while Nvidia's price-to-sales ratio remains well above its historic norm.
The trading activity observed from insiders supports the thesis that they don't view their stock as a bargain -- and that's a potentially worrisome realization for Wall Street and investors.
