On Monday, as Washington Post Co. chief executive Fred Ryan began to address his full staff regarding the news of his just announced departure, his microphone cut out. This was not at all his fault, of course, and yet it provided a fitting metaphor for his final years of his reign—a flaccid denouement to an epic run in which, after rescuing the moribund Post with the Bezos dowry, the company had become lethargic and flat-footed. Fitting, too, was the image of the svelte gray-haired Reaganite tapping away at the device (is this thing on…?) while several reporters began quietly delighting in his misfortune. “Couldn’t even say bye with a working mic,” one journalist scoffed afterward.

Ryan’s legacy at the Post Co. is, in many ways, a tale told in two countervailing acts. The first began in 2013, shortly after Jeff Bezos bought the paper for a criminally inexpensive price of $250 million and appointed Ryan, the former Reagan aide-turned-Politico executive, as his inaugural publisher and C.E.O. Working with Marty Baron, the legendary executive editor, Ryan deployed Bezos’s vast resources to dramatically overhaul the company’s digital operation and then rode the wave of liberal panic over Trump’s political ascent and presidency, growing the paper’s paid subscriber count from 35,000 to 3 million in the process.