Over the years I ran into Ben Bradlee a few times, mostly when I was the finance editor of the International Herald Tribune -- The Washington Post then owned a third of its stock -- and even had dinner with him once in Paris, with Donald Graham (of The Post's owning family) and a secretary. He couldn't have been more charming or friendly.
While full of bonhomie, Bradlee evoked a powerful sense of privilege that I sometimes found a bit off-putting. But then, he grew up in a Boston Brahmin family, albeit one that had somewhat straitened circumstances (compared to its earlier condition) because of the Great Crash of 1929. (Still, there were enough rich relatives around to send him to fancy schools.)
Because of the immense confidence with which he carried himself, his theatricality, his studly good looks, his memorable mix of the patrician and a swearing sailor, and his social connections with the owners of The Post and other grandees, his Post editorship developed into a cult of personality, which I think he much enjoyed cultivating.
It got rather silly: Many of the other senior editors and reporters started to wear his brand of expensive shirts from London, use many of his salty and other expressions and laugh at even his bad jokes. I witnessed this suck-up in full flower in a couple of news meetings at The Post in which he presided.
He had a tendency to studiously ignore (and even try to make leave the paper) those who had fallen out of his favor, such as by boring him. This created an atmosphere of fear in the newsroom that competed with the pride and energy that the rise of the paper and his charisma fueled. A friend of mine there, an editor, used to joke that he sat at his desk everyday "watching the blood drip down the walls.'')
Whatever, he was a great editor, especially for someone who did remarkably little hand's-on editing, which would have required missing too many Georgetown dinner parties. He made the right choices for the paper and the nation in printing the Pentagon Papers and pushing the Watergate stories. However, I'm not sure how much social courage was involved in those decisions; most of his social group hated Nixon. It's possible, however, that printing the Pentagon Papers could have landed him in jail for contempt of court. I suspect he would have reveled in that publicity.
In any event, Bradlee picked the perfect stretch of time to work in the newspaper business.