It’s telling that the New York Times Co.’s $550 million acquisition of sports website The Athletic is the storied newspaper’s biggest takeover since it splashed $1.1 billion to buy the Boston Globe in 1993. It heralds a fresh experiment in how to sell more news to a generation of readers raised online that, if successful, could prove a model for other media giants to emulate.
The Boston Globe deal marked the pinnacle of the Grey Lady’s ill-fated expansion into regional news: at the time it owned 31 regional newspapers, 20 magazines, five television and two radio stations. The advent of the internet era meant the subsequent two decades were not kind. As the web hoovered up advertising dollars and readers alike, net debt ballooned to six times Ebitda, an earnings measure, by 2009.