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He is suing various media organizations — including the board of the Pulitzer Prizes and the Des Moines Register and its parent company, Gannett — over journalism he claims was libelous or unfair.

A legal expert gave the litigation little chance of succeeding, and press freedom advocates protested it as a another retaliatory measure designed to chill media outlets from making fair assessments of the incoming president — particularly after other Trump lawsuits against media institutions including CBS News, ABC News and the board that oversees the Pulitzer Prizes.

“I’m extremely proud of work we’ve done right,” he said, “and we’ve done a lot right,” he said, pointing to six Pulitzer Prizes the paper has won during his ownership, among other honors.

When The Washington Post’s staff gathered in the newsroom in early May to celebrate winning three Pulitzer Prizes, one person was conspicuously absent: Will Lewis, the company’s publisher and chief executive.

During his tenure, the paper maintained its reputation for high journalistic standards and won Pulitzer Prizes, including for revealing hush-money payments by Donald J. Trump before the 2016 election.