The New York Times largest shareholder, Mexican telecommunications billionaire Carlos Slim, sold half of his common stock and warrants in the company, valued at about $240 million, on Tuesday.

Slim provided a $250 million loan to the Times back in 2009 with the company struggling following the 2008 recession.

The Times paid the loan off six years ago, but Slim exercised his option on warrants to purchase Times shares at a discounted price.

The selloff was made public in an appendix to a regulatory filing on Dec. 4 that was first reported by Bloomberg News on Tuesday.