Carr’s career has followed a remarkable arc. He began at the Twin Cities Reader, an alternative weekly in Minneapolis, and later spent five years editing Washington City Paper, another alternative. Along the way, he became a coke addict who sold drugs, beat up women, and lost his kids to foster care. (He wrote a best-selling book about his days as a junkie).

At the Times, he began as a grunt on the media beat, but he quickly rose. In 2005 he started the paper’s Carpetbagger blog, in which he handicapped the Oscars and interviewed stars on the red carpet. Since then, he’s been lionized in a documentary, been interviewed by Aaron Sorkin, and written a column that allows him to mix with the famous and powerful. He’s become, in short, the very type of insider that the hard-hitting David Carr would gleefully expose.

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Michael Massing is a contributing editor to CJR and the author of Now They Tell Us: The American Press and Iraq.