What if you bought Caterpillar in 1990?
US Industry · Machines. The hindsight answer, year by year, against the only benchmark that matters.
Could you have picked it? Play64.3× · S&P 500 same money: $19,429
$1,000 in Caterpillar at the start of 1990 would be worth about $64,286 today — 64.3 times your money, and ahead of the S&P 500 over the same stretch.
The story
Caterpillar makes the yellow machines that dig mines and build roads, plus engines and turbines. For an investor it was mostly a bet on global construction and commodities. The 2000s China boom was its golden age: mining companies needed ever bigger trucks and loaders, and the shares roughly tripled from 2003 to 2008.
After a sharp crisis drop, Caterpillar doubled down on mining, buying Bucyrus, a maker of huge mining machines, in 2011, close to the top of the commodity supercycle. When metal prices fell, mining capital spending collapsed, and in 2013 Caterpillar also wrote off most of a Chinese mining-equipment acquisition after finding accounting misconduct. The shares went sideways for much of the 2010s. The 2020s brought a surprise second act: an infrastructure spending bill and, especially, demand for backup generators and gas turbines to power AI data centres. Caterpillar's power business became a key growth driver, and the shares rose to multiples of their 2020 level.
The lesson: Cyclical companies punish buyers who extrapolate peak conditions; acquisitions made at the top of a cycle tend to become write-downs later.
$1,000 invested at the start of each year
| Bought in | Price then | Worth today | S&P 500 would be | Multiple |
|---|---|---|---|---|
| 1990 | $7.00 | $64,286 | $19,429 | 64.3× |
| 1995 | $14.00 | $32,143 | $14,783 | 32.1× |
| 2000 | $24.00 | $18,750 | $4,626 | 18.8× |
| 2003 | $23.00 | $19,565 | $7,727 | 19.6× |
| 2005 | $49.00 | $9,184 | $5,763 | 9.2× |
| 2007 | $62.00 | $7,258 | $4,789 | 7.3× |
| 2008 | $72.00 | $6,250 | $4,626 | 6.2× |
| 2010 | $58.00 | $7,759 | $6,071 | 7.8× |
| 2012 | $92.00 | $4,891 | $5,312 | 4.9× |
| 2015 | $91.00 | $4,945 | $3,301 | 4.9× |
| 2018 | $158 | $2,848 | $2,519 | 2.8× |
| 2020 | $148 | $3,041 | $2,092 | 3.0× |
green = beat the S&P 500 · red = lost money
Best entry point in our set: 1990, turning $1,000 into $64,286. 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. Caterpillar is one of 258 positions on the wheel — including the ones that went to zero.
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