On the one hand, he was from the Boston WASP establishment. On the other hand, he entered the rough-and-tumble newspaper business and even in that world was known for his aggressiveness. Also, his risk-taking, as was played out with The Washington Post's bet on Deep Throat.
There is no more WASP establishment. And the newspaper world he put his imprint on is no more. The media are dominated with entities like Business Insider which was born digital. That world is producing different kinds of legendary figures.
And Bradlee is also no more. As The Wall Street Journal reports, he died of natural causes in his home, at age 93 (sub. req.)