Berlin's Four Essays on liberty remains one of my most treasured moments (and books) in my intellectual journey. Lucid and intelligent writing, with none of the obscurantism. Of course, I have all Berlin's books.
A recent book and very good read I can recommend is Isaac & Isaiah by Caute which charts the rivalry between Isaiah Berlin and Isaac Deutcher (the author of an influential biography on Trotksy). I had not been aware of Berlin's (priviledged) background and the book helped contextualise his thinking.
Sorry in advance because I'm not trying to be difficult, but I've never been able to get anything out of Berlin's writings, other than some of his gossipy letters. He was a sparkling socialite of the academic elite, which makes him a historical figure in that way. But what valuable or original ideas did he come up with? The many essays about him, including the OP, never seem to specify this, at least not in any way that registers with me. It all seems so mushy and middling.
You don’t find the concept of “positive and negative liberty” to be specific and useful? Personally, I think it’s incredibly insightful yet fundamentally very simple, which is the mark of a good thinker IMO.
A recent book and very good read I can recommend is Isaac & Isaiah by Caute which charts the rivalry between Isaiah Berlin and Isaac Deutcher (the author of an influential biography on Trotksy). I had not been aware of Berlin's (priviledged) background and the book helped contextualise his thinking.