The $250 million investment by tycoon Carlos Slim complements his telecommunications holdings in Latin America, and gives Slim, reputed to be the world's second-richest man, the prestige of owning a sizeable stake in one of the world's best-known and most influential newspapers.
"By having a stake in the New York Times, he's basically projecting himself as a powerbroker in this country, regardless of how his investment does," said Armand Peschard-Sverdrup, a senior associate of the Center For Strategic and International Studies, a Washington think tank.
Slim also stands to make a sweet profit off his investment - The Times will pay him 14 percent interest along with warrants he can use to boost his stake in the company from 6.9 percent to 17 percent.
The Times announced late Monday the financing agreement with Slim's companies Banco Inbursa and Inmobiliaria Carso for $125 million each. Times President Janet L. Robinson said the cash infusion will be used to refinance existing debt and will provide the company with increased financial flexibility.
"The New York Times needs money in the next few months, and Slim has it," said Shannon K. O'Neil, a Latin American expert at the Council on Foreign Relations in New York.
New York Times shares slipped 8.6 percent to $5.86 in morning trading Tuesday, the first trading day after the company announced the deal.
In September, Slim and members of his family purchased $128 million worth of the company's publicly traded shares - an investment the Times said has since fallen to $58 million.
This time, he's locking in his profits - the Times said Slim would buy six-year notes in the company with warrants that are convertible to common shares. The Times will pay 11 percent of the interest on the notes in cash and 3 percent in additional bonds, the newspaper reported.
This kind of guaranteed return is similar to the 10 percent annual dividends insisted upon by financier Warren Buffett and General Electric Co.
Slim gets no representation on the Times' board, and no special voting rights. But when he exercises the warrants, he would own up to 17 percent of the company's common stock, making him one of the company's largest shareholders. The Ochs-Sulzberger family owns about 19 percent of the company but controls it through a special class of supervoting shares.
"I don't see him meddling," said George Grayson, a Mexico expert at the College of William & Mary in Virginia. "Those of us who read the New York Times everyday, I think will be uncorking champagne bottles because unless these papers are infused with capital they are going to cut back services."
Slim is part of a crop of emerging-market billionaires, from Mexico to Russia, who are on a shopping spree now that the recession has slashed the prices of some of America's best-known companies, and other sources of credit have dried up.
Slim recently upped his stakes in Saks Fifth Avenue, and his Inbursa brokerage in Mexico bought at least $150 million of Citigroup's sinking shares.
"A lot of foreign business tycoons are bargain shopping, and this is something the U.S. has no choice but to get used to," Peschard-Sverdrup said. "We're going to have all these various foreign interests owning various U.S. assets. It's one of the things that the recession ultimately has accelerated."
Some investments seem risky at best. Retail electronics tycoon Ricardo Salinas Pliego, another Mexican billionaire, raised his stake in bankrupt Circuit City to 28 percent before the company announced last month that its U.S. stores will go out of business.
But Slim has built his fortune by turning around troubled companies. He learned how to make his money from his father, a Lebanese immigrant and Mexico City shopkeeper who bought cheap property.
Slim got his start in the cigarette business and made it big in 1990, taking control of Mexico's state-owned telephone monopoly. Telefonos de Mexico SA, or Telmex, still operates more than 90 percent of the nation's fixed-line phone services, while his America Movil SAB is Latin America's largest mobile phone service provider.
"He transformed a state-owned company into one of the most profitable businesses in the country," said analyst Jose Coballasi of Standard & Poor's in Mexico City.
Now worth an estimated $59 billion, Slim owns hundreds of businesses in Mexico, from bakeries to clothing stores to record shops and drug stores. His industrial-retail conglomerate Grupo Carso is solid, enjoying liquidity despite the crisis, Coballasi said.
Opponents say Slim, 68, runs ruthless monopolies that illegally block competitors, and is known for hostile takeovers. After Slim boosted his stake in Saks from 17.2 million shares to 25.3 million shares late last year, the company's board introduced a "poison pill" into its share structure, apparently to prevent a Slim takeover.
O'Neil says Slim could help save the Times by "providing essentially a loan for the paper, to provide them time to make the changes necessary to adjust to the changing media world and become more profitable again."
Still, she worries about one man having his hands in so many communications companies at once - telecommunications, Internet, cable and now news. "The familiar lines between all of these businesses are disappearing, and Slim, like others, is involved in all of them," said O'Neil.