Good evening, I’m Dylan Byers.

Welcome back to In The Room, my biweekly private email on the media industry. This evening, a closer look at the consequences of the Times’ compressed payscale, which has created a Sophie’s Choice situation for many of the paper’s mid-to-top-tier journalists. Plus, notes on Jake Tapper’s early outing as a CNN primetime host.

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The Times was perhaps a victim of its own success in this regard: over a decade, it had recruited many of the most ambitious journalists of the era to work almost exclusively in service of the paper; now it was being forced to reckon with those ambitions—a new title or assignment, more leeway, et cetera—which didn’t always align with what was best for the Times. In the old days, the Times could, and often did, tell reporters to...