In an interview last year, Mr. Freeman argued that the austere cuts enacted at his newspapers reflected a more realistic understanding of the industry’s direction and better positioned Alden-owned publishers for the pandemic’s downswing. “We were prepared for a real step down in terms of a recession because we were honest about what was needed in the future,” he said. “Numbers don’t lie.” The newspaper industry’s numbers looked bleak even before the pandemic. Annual advertising revenue dropped 70%, or $34 billion, between 2005 and 2018, according to estimates by the Pew Research Center. More than 1,800 newspapers closed between 2004...