What if you bought TWA in 1990?
US Consumer · Airlines. The hindsight answer, year by year, against the only benchmark that matters.
Could you have picked it? Play0× · S&P 500 same money: $19,429
Every dollar is gone. TWA went bankrupt in 2001, so $1,000 invested in any of these years is worth exactly nothing today.
The story
Trans World Airlines had a storied past, including the Howard Hughes era and Eero Saarinen's swooping terminal at JFK. Its modern decline began in the 1980s when corporate raider Carl Icahn took control, then loaded the airline with debt in a leveraged deal while selling off valuable assets, including its London routes. TWA entered the 1990s weighed down by obligations it could not service.
It filed for Chapter 11 in 1992, again in 1995, and a third time in 2001, earning a reputation as a frequent bankruptcy filer. In between, it struggled with an old fleet, labour disputes and its hub in St. Louis. In July 1996 TWA Flight 800 exploded off Long Island, killing all 230 people aboard; investigators blamed a fuel tank ignition. The final bankruptcy in early 2001 came alongside a deal to sell its assets to American Airlines, which absorbed the planes, routes and staff. The old shareholders received nothing, as the price path makes plain.
The lesson: Repeated bankruptcies are a warning, not a buying opportunity; a company that keeps restructuring has usually lost its ability to cover its costs.
$1,000 invested at the start of each year
| Bought in | Price then | Worth today | S&P 500 would be |
|---|---|---|---|
| 1990 | $15.00 | $0 | $19,429 |
| 1995 | $4.00 | $0 | $14,783 |
| 2000 | $3.00 | $0 | $4,626 |
green = beat the S&P 500 · red = lost money
There was no good entry point: every starting year ends at zero. The same $1,000 in the S&P 500 from 1990 would be $19,429 today.
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. TWA is one of 258 positions on the wheel — including the ones that went to zero.
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