Billionaire Carlos Slim is poised to become the largest shareholder in the New York Times Co. after already almost doubling his money from an investment that helped the newspaper get through the financial crisis.

Slim, who has amassed a $73 billion fortune by spotting depressed valuations, loaned $250 million to Times Co. in January 2009. After already getting repaid and then some, the world’s second-richest person is now on track to boost his holdings if he exercises options by their Jan. 15 deadline. Slim would then own almost 17 percent of the Times Co.’s Class A shares, a stake valued at about $349 million.

While Slim’s financial return shows just how much Times Co. sacrificed for his help at the time, it also illustrates how confident he was in the storied newspaper’s future -- even as readers and marketers flocked to the Internet where content was largely free and ad rates were cheaper. And he hasn’t been alone in his faith in media: billionaire Jeff Bezos purchased the Washington Post in 2013 and Warren Buffett has invested in a number of local newspapers.

Slim deciding to hold on to a bigger stake would be “a vote of confidence in the Times,” said Ken Doctor, an independent media analyst for Newsonomics. “It is largely the wealthiest people who have the capacity to take on what is still a flier on the business future of the news industry.”

2009 Loan

When 74-year-old Slim agreed to loan Times Co. money in 2009, the company had just canceled its dividend to preserve cash and a credit line was set to expire. Slim’s investment bought the company enough time to find buyers for assets like the Boston Globe.

Since then, Times Co. has cleaned up its balance sheet, put up a paywall for its website and introduced new digital products.

The warrants Slim gained through the loan deal let him buy shares for about $6.36 apiece, according to regulatory filings, about half of Times Co.’s $12.57 closing price on Monday. That gives Slim $6.21 in potential profit for each of the 15.9 million shares he’s allowed to buy, amounting to almost $100 million, according to data compiled by Bloomberg.

That would boost his total stake to about 27.8 million Class A shares, or about 16.8 percent.

Today, Times Co. shares rose 1.6 percent to $12.77 at 9:39 a.m. New York time, giving the company a market value of about $1.9 billion.

Keep Shares

Slim planned to exercise the warrants and hold on to the expanded equity stake, rather than sell the shares for an immediate profit, a person with knowledge of the matter said last year.

Arturo Elias Ayub, a spokesman for Slim, didn’t reply to requests for comment. Abbe Serphos, a spokeswoman for Times Co., declined to comment.

Even with the bigger stake, an unwanted takeover would still be difficult because the controlling owners -- the Ochs- Sulzberger family -- hold voting shares that give them a firm grip on board seats. Slim’s stake only allows him to vote for Class A directors, a group that represents no more than a third of the company’s board seats. The family’s Class B shares, which aren’t publicly traded, elect the remaining two-thirds of the board.

“What most people care about is whether or not Slim has bigger aspirations in ultimately buying the company,” said William Bird, a media analyst at FBR & Co. in New York. Such a scenario is “difficult, if not impossible, to imagine” because the family has said the paper is not for sale, Bird said.

Slim would have been better off exercising his options in April when the stock was 37 percent higher at $17.26.

Trying Year

The last year has been a tumultuous one for Times Co., both in the newsroom and on the business side. In May, Chairman and Publisher Arthur Sulzberger Jr. ousted Jill Abramson as executive editor after less than three years on the job. And at the end of last year, the paper cut more than 100 newsroom employees through buyouts and firings to save costs.

Meanwhile, the company is trying to maintain growth in online subscriptions, which totaled about 875,000 at the end of the third quarter, and print readership has continued to decline. Digital ad revenue has increased, but not enough to make up for the drop in print advertising.

Slim has “turned out to be very fortunate because the company’s performance certainly wouldn’t warrant a doubling” of profits, said Ed Atorino, a New York-based analyst at Benchmark Co. “They continue to reduce the staff, and they’re doing everything to ride out what they hope is not a permanent decline in advertising.”

Even without the warrants, Slim had made a profit on his investment. The Times paid Slim back in 2011, including a 12 percent premium for early payment. The loan had carried an annual interest rate of 14 percent.

Dividend Payments

Plus, Slim has collected about $2.9 million in dividend payments since the dividend was reinstated in 2013. If Slim holds on to his bigger stake, he’ll collect about $1.1 million in dividend payments each quarter. Slim didn’t disclose what he paid for the bulk of the stock he accumulated before the loan deal, making it difficult to calculate his profit on that stake.

The Times Co. investment is only one element of Slim’s empire, which ranges from banking to energy to retail. The bulk of his riches come from a majority stake in America Movil SAB, the mobile-phone operator trying to sell assets in Mexico to reduce its market share.