How Donald Trump strengthened The New York Times and grew a Mexican billionaire's fortune

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I’ve been thinking about The New York Times lately, and not so much because “the failing New York Times” is in Donald Trump’s crosshairs—although there is a connection (more on that in a second), but because the Times has become emblematic of two things I’m keenly interested in, namely, the digital revolution transforming the media business, and making money in the stock market.

Simply put, the Times has had a bit of success with the former, which has led to a bit of success with the latter.

Ten years ago though the opposite was true. It was the worst of times for the Times. The company that owned the Paper, as it is called by insiders, actually was failing, both in terms of its business model and as an investment.

In those dark days—the nadir of the Great Recession—it was legitimate and even logical to call into question the Times as a going concern. Advertising was tanking and so too print subscriptions. An ambitious paywall scheme—launched in 2005—was an “embarrassing flop,”a former Times editor told me.

‘The paper’s future doesn’t look good’

“End Times” was the headline of a piece in the Atlantic (Jan/Feb 2009), which asked and (partly) answered this question: “...what if The New York Times goes out of business—like, this May? It’s certainly plausible. Earnings reports released by the New York Times Company in October indicate that drastic measures will have to be taken over the next five months or the paper will default … the paper’s future doesn’t look good.”

Arthur Sulzberger Jr., chairman of The New York Times Co., speaks during the New York Times DealBook conference in New York, U.S., on Thursday, Nov. 10, 2016. The event brings together CEOs, leading figures in finance, and experts from diverse industries to assess the challenges and opportunities that will define the deal world of tomorrow. Photographer: Michael Nagle/Bloomberg via Getty Images
Arthur Sulzberger Jr., chairman of The New York Times Co., speaks during the New York Times DealBook conference in New York, U.S., on Thursday, Nov. 10, 2016. Photographer: Michael Nagle/Bloomberg via Getty Images

But a funny thing happened on the way to bankruptcy court.

An unlikely savior emerged you may recall, in the form of Mexican billionaire Carlos Slim Helu. The previous September, (that is September 2008, when the U.S. financial system was melting down), Slim bought a 6.4% stake in The New York Times Company, or 9.1 million shares, worth some $127 million. (The stock was then around $13.)

Immediately after Slim’s purchase, the situation became much worse, both for the global economy and as noted for the Times. But as talk of bankruptcy amplified, Slim stepped up again. In January he loaned the company $250 million “in the form of six-year notes with warrants that are convertible into common shares, the company said in a statement. The notes also carry a 14 percent interest rate, [emphasis added] with 11 percent paid in cash and 3 percent in additional bonds,” the Times dutifully reported on itself.

Still the market was unimpressed. In February 2009, New York Times stock dropped to a low of $3 and change. The Atlantic piece looked prescient and Slim’s investment of some $327 million appeared to be lost money.