American Express’s CEO Sold $99 Million of Stock the Day Before the Crash
A nine-figure stock sale landed one day before a $2.5 trillion tech rout, and the timing looks damning. The filing details, a precedent from earlier years, and one unchecked box on the form complicate the story.
This post may contain links from our sponsors and affiliates, and Flywheel Publishing may receive compensation for actions taken through them.
On November 4, 2026, Stephen Squeri, the chairman and CEO of American Express (NYSE:AXP | AXP Price Prediction), exercised 299,401 stock options at $148.45 each. He sold every resulting share that same day for about $99.45 million. On the following day, tech stocks fell sharply, and the Nasdaq Composite lost about $2.5 trillion in market value.
The disclosure was accepted after the close on November 6, so AXP has not traded on it yet. The stock closed that day at $320.99, down 1.22%. That is about 3.4% below its average sale price of $332.16.
At first glance, the timing looks bearish. The filing details point the other way, although one unchecked box on the form is worth mentioning.
What Squeri Filed
He sold in four blocks at weighted averages of $330.52, $331.64, $332.42 and $332.98. Individual trades ran from $329.90 to $333.20. A notice filed on November 4 listed a total market value of $99,448,587.
The options came from a performance award granted in October 2022. Its final 25% portion, which was 74,850 options, vested on October 31, 2026, after the performance goals were met.
Exercising the options cost about $44.4 million, which left a gross spread of roughly $55.0 million before taxes. The spread is his gain, and the headline figure is gross proceeds.
The Rule 10b5-1 box is unchecked. That box flags trades scheduled ahead of time under a preset plan, and the filing gives no reason for the sale.
Why the Timing Looks Worse Than It Is
On November 4, AXP opened at $334.00 and traded between $325.37 and $337.25. It closed at $332.59, up 2.18%.
On November 5, the stock reached $343.89. It then closed at $324.97, down 2.29%, because the selloff started in technology stocks and spread to the rest of the market.
He has done this before, though.
On November 7, 2024, he exercised options and sold 170,632 shares at weighted averages of $285.49 to $288.05, for about $48.9 million. On February 1, 2022, he sold 267,656 shares for about $47.8 million.
The latest sale is roughly double each of those. Executives often sell shares from vested options to cover taxes and to spread out wealth tied up in one company. For that reason, these sales tell you less than open-market sales of stock held for years.
He still directly owns 60,567 shares. Another 163,292 sit in the Stephen J Squeri 2025 Master GRAT, a type of trust used for estate planning, and about 130 are in his retirement plan.
What Drives American Express Stock
In the third quarter, adjusted EPS came in at $4.68, beating the $4.5063 consensus. Billed business, meaning total spending on Amex cards, grew 8%, and the net write-off rate improved to 1.8%.
Management raised its full-year adjusted EPS guidance to $17.60 to $17.90 and is cutting about 5% of its global workforce. A market selloff only hurts the business if it spreads into premium consumer spending.
What AXP Investors Should Weigh Next
Several data points support a bullish reading. The sale turned vested options into cash, and the business beat EPS estimates in every reported 2026 quarter. The stock is down 12.26% year to date, inside a 52-week range of $290.97 to $387.49. It pays an annual dividend of $3.80, a yield of 1.18%.
The bullish reading weakens if AXP closes below $290.97, or if a later filing shows Squeri selling the shares he owns directly rather than newly vested options.
Contact [email protected] for any questions or corrections.
Omor Ibne Ehsan is a writer at 24/7 Wall St. He is a self-taught investor with a focus on growth, cyclical, and dividend equities that have strong fundamentals, value, and long-term potential. He also has an interest in high-risk, high-reward investments such as penny stocks.
