John Dewey is like a lovable uncle. If Keith Olbermann didn't have such an attitude problem, he'd be like John Dewey.
When we read Dewey nowadays, us modern American liberals and leftists recognize that we've taken his attitudes totally, utterly to heart. Yeah! Democracy via activism! Education outside the ivory tower! Social constructivism! You can tell that Dewey was one of the most humane thinkers of his time, unafraid to challenge the orthodoxies of political or academic institutions. He could raise the blood pressure of the Coolidge Republicans and the Harvard Hegelians with his eyes closed and a hand tied behind his back, and still have time for breakfast.
The inherent problem, though, is that this provides relatively little that enlightens the modern reader, especially with these brief snippets. I'd be intrigued to read his full length works. Perhaps they're more argument driven.