What if you bought New York Times in 1990?
US Consumer · Media. The hindsight answer, year by year, against the only benchmark that matters.
Could you have picked it? Play4.6× · S&P 500 same money: $19,429
$1,000 in New York Times at the start of 1990 would be worth about $4,583 today. A plain S&P 500 index fund over the same years would have made more — the boring option won.
The story
The New York Times Company is controlled by the Ochs-Sulzberger family through a dual-class share structure, which has protected the newsroom and occasionally frustrated shareholders. Around 2000 it was a classic print empire with regional papers, TV stations and the Boston Globe, bought in 1993 and later sold for a small fraction of the price. Classified ads migrated to the web, print circulation slid, and by the 2008-09 crisis the company was borrowing from Mexican billionaire Carlos Slim on expensive terms and suspending its dividend.
The turnaround began with a metered paywall in 2011, which skeptics called hopeless. It worked. The Times sold off non-core assets and rebuilt itself as a subscription business, adding Wirecutter, The Athletic and, in 2022, the word game Wordle. Games and cooking apps became reasons to subscribe alongside the journalism. Digital subscribers passed ten million, and the share price that sat in single digits around 2012 climbed back above its dot-com high.
The lesson: Companies written off as obsolete can reinvent themselves when they own a brand people will pay for directly; the lowest point is rarely obvious while you are standing in it.
$1,000 invested at the start of each year
| Bought in | Price then | Worth today | S&P 500 would be | Multiple |
|---|---|---|---|---|
| 1990 | $12.00 | $4,583 | $19,429 | 4.6× |
| 1995 | $11.00 | $5,000 | $14,783 | 5.0× |
| 2000 | $48.00 | $1,146 | $4,626 | 1.1× |
| 2003 | $46.00 | $1,196 | $7,727 | 1.2× |
| 2005 | $40.00 | $1,375 | $5,763 | 1.4× |
| 2007 | $24.00 | $2,292 | $4,789 | 2.3× |
| 2008 | $17.00 | $3,235 | $4,626 | 3.2× |
| 2010 | $12.00 | $4,583 | $6,071 | 4.6× |
| 2012 | $8.00 | $6,875 | $5,312 | 6.9× |
| 2015 | $13.00 | $4,231 | $3,301 | 4.2× |
| 2018 | $18.00 | $3,056 | $2,519 | 3.1× |
| 2020 | $32.00 | $1,719 | $2,092 | 1.7× |
green = beat the S&P 500 · red = lost money
Best entry point in our set: 2012, turning $1,000 into $6,875. The S&P 500 from that same year: $5,312.
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. New York Times is one of 258 positions on the wheel — including the ones that went to zero.
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