What if you bought American Express in 1990?
US Finance · Cards. The hindsight answer, year by year, against the only benchmark that matters.
Could you have picked it? Play43.8× · S&P 500 same money: $19,429
$1,000 in American Express at the start of 1990 would be worth about $43,750 today — 43.8 times your money, and ahead of the S&P 500 over the same stretch.
The story
American Express began as a freight company and became a travel and payments brand built around the prestige of its charge cards. In the early 1990s it was a troubled conglomerate; under new leadership it spun off Lehman Brothers and refocused on cards, and by the late 1990s the stock had risen severalfold. Warren Buffett, a shareholder since the 1960s, was among its most loyal investors.
Unlike Visa and Mastercard, Amex both runs the network and lends to cardholders, so credit losses hit it directly. In 2008 it became a bank holding company to access government support and saw shares fall sharply. Its business model, catering to affluent spenders who pay high annual fees in exchange for rewards and lounge access, then proved remarkably resilient. Losing the Costco partnership in 2016 was a notable blow, but Amex leaned into premium cards, younger customers and travel. The stock roughly tripled from 2020 to 2026, showing how valuable a brand can be when its customers treat paying a fee as a status symbol.
The lesson: Pricing power rooted in brand and customer identity can let a company raise prices while still attracting customers who feel they get more than they pay.
$1,000 invested at the start of each year
| Bought in | Price then | Worth today | S&P 500 would be | Multiple |
|---|---|---|---|---|
| 1990 | $8.00 | $43,750 | $19,429 | 43.8× |
| 1995 | $10.00 | $35,000 | $14,783 | 35.0× |
| 2000 | $50.00 | $7,000 | $4,626 | 7.0× |
| 2003 | $36.00 | $9,722 | $7,727 | 9.7× |
| 2005 | $56.00 | $6,250 | $5,763 | 6.2× |
| 2007 | $60.00 | $5,833 | $4,789 | 5.8× |
| 2008 | $52.00 | $6,731 | $4,626 | 6.7× |
| 2010 | $40.00 | $8,750 | $6,071 | 8.8× |
| 2012 | $47.00 | $7,447 | $5,312 | 7.4× |
| 2015 | $93.00 | $3,763 | $3,301 | 3.8× |
| 2018 | $100 | $3,500 | $2,519 | 3.5× |
| 2020 | $125 | $2,800 | $2,092 | 2.8× |
green = beat the S&P 500 · red = lost money
Best entry point in our set: 1990, turning $1,000 into $43,750. The S&P 500 from that same year: $19,429.
Now try it without hindsight. The wheel decides the year and the asset class, you pick the position, ten seconds a pick, and we simulate to today. American Express is one of 258 positions on the wheel — including the ones that went to zero.
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