In 2013, a reclusive New York tycoon and his wife began buying up expensive Palm Beach real estate—lots of it. First they bought seven mansions for a total of $23 million. Then another four “moderately priced” homes for $8.4 million. Then five more for $23 million. None of them were purchased in the tycoon’s name. They weren’t purchased in his wife’s name, either. Instead, the homes were deeded to limited-liability companies, including L. Jakes LLC and 124 Coconut Row LLC.
Think of those luxury homes as the shuttered offices and fired workers of hometown newspapers across the United States, because gutting those newspapers helped make spending $57.2 million on 16 Palm Beach mansions a trifling expense for the tycoon.
His spending spree began after the tycoon acquired two firms, the Journal-Register and MediaNews Group, which would merge into one of America’s largest newspaper chains, Digital First Media. It continued under the veil of yet more limited-liability companies that likewise owned luxury homes. The only thing linking all these purchases was the same postal address in Manhattan’s glamorous Lipstick Building. There, within the tycoon’s privately held investment firm, his personal real-estate deals were commingled with the sales of scores of newsrooms, printing plants, and office buildings that previously belonged to small hometown newspapers across the United States.
The tycoon continued to finance his lavish lifestyle by purchasing and then destroying newspapers. His henchmen—young executives in expensive suits with no experience in the news business—laid off hundreds of journalists and other news workers. They ultimately closed or radically downsized such venerable papers as the Oakland Tribune, the San Jose Mercury News, the St. Paul Pioneer Press, and The Denver Post. At the Mercury News, the newspaper’s printing press was literally dismantled and carted away, which one staff reporter likened to “watching a heart being ripped out.”
The tycoon behind all this private profit and public destruction is Randall D. Smith, a seasoned Wall Street operator in his mid-70s who shuns publicity. Smith is the founder and chief of investments at Alden Global Capital, which manages $2 billion worth of assets. He has no experience with actually managing a newspaper, and his professional history reflects no interest in journalism beyond profiteering. Rather, he is what is known on Wall Street as a “vulture capitalist.” Or, as he prefers to phrase it in one of the company’s brochures, Smith invests in “distress.”