Bad Boys

When investors show up, promising to reinvent or save the news industry, it often portends chaos. Some of the most notorious figures have cost thousands of journalists their jobs.

Heath Freeman Known as a “vampire,” Freeman owns more than two hundred outlets through his hedge fund, Alden Global Capital. Since taking control of Digital First Media, in 2011, Alden has cut two out of every three staff positions in its newsrooms. After the Denver Post went through Alden’s layoff procedures, Freeman bought a $4.8 million mansion, the price of which could have paid the salaries of twenty-five Post reporters for more than two years.

Shane Smith A cofounder of Vice, Smith presents himself as a punk pioneer of digital media; his antics and lies have attracted investors, but also resulted in financial disaster. His former girlfriend told New York magazine, “Shane would talk all the time about how stupid people were for giving them money.”

Bryan Goldberg A founder of Bleacher Report, Goldberg went on to become a media slumlord with the Bustle Digital Group, which owns Bustle, Elite Daily, Mic, and other outlets. He slashes and burns and union-busts; in 2018, he bought Gawker. Elizabeth Spiers, a founding editor of Gawker, has called Goldberg’s strategy “Lazy Entrepreneur Solipsism.”

Jim Spanfeller In the aughts, Spanfeller oversaw the website of Forbes; in 2019, when Great Hills Partners, a private equity firm, acquired G/O Media, he was installed as CEO. At Deadspin, Spanfeller ran headfirst into conflict; after the site’s editor submitted her resignation, he “let out a cruel barking laugh.” Soon, all twenty people working for Deadspin quit.

Anthony Melchiorre As the founder of Chatham Asset Management—the hedge fund that owns American Media Inc.—Melchiorre publishes the National Enquirer and other tabloids. Chatham acquired McClatchy’s newspapers, including the Miami Herald, the Kansas City Star, and the Sacramento Bee. Melchiorre has been called (by his former boss at Morgan Stanley) a “street fighter”; as a press boss, he’s kept a lower profile.

Guy Gilmore The COO of Digital First Media Inc., a newspaper publisher owned by Alden Global Capital, Gilmore waited just a week after the East Bay Times and the Mercury News had won a Pulitzer Prize to cut twenty positions from those newsrooms. Recently, Gilmore opted to outsource news design of Digital First’s California newspapers to the Philippines, shrinking the staff even more. A former colleague of Gilmore’s told The Street, “He may not be that popular with those who work for him, but he makes his numbers.”

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Feven Merid is CJR's senior staff writer.