Most have reservations on him as a historian, but Bert Sugar really did have a way with words, especially comedic phrasing. For pure prose and writing though, I'd have to say Pierce Egan and Gilbert Odd.
For me, I'd say trainers like Gil Clancy and Manny Steward. Listening to them, you can just tell they see things many don't. They knew boxing as well as anyone who's ever lived. I do like hearing Roy Jones talk though. One of the few fighters who doesn't talk rubbish. (I'm definitely not saying fighters don't know boxing-of course they do-but some talk the biggest pile of crap you're ever likely to hear) Boxing scribes and journalists... depends on their pedigree. Matchmakers like Teddy Brenner definitely knew boxing.
For boxers Jack Dempsey in his book 'Championship Fighting' and for boxers who are commentating it's hard to not like Roy Jones and Paulie Malinaggi, or George Foreman if you want to laugh, not the most insightful though aha. For historians Henry Hascup and Cliff Rold have taught me plenty and always have some insightful input, not a fan of Bert Sugar but can see why some like him.
Just in terms of analyzing the skills and tactics of individual fighters? Wilson Kayden on Youtube was excellent.
Ray Arcel, Eddie Futch, Emanuel Stewart, Bert Sugar, Larry Merchant, Al Bernstein, Dempsey, Gil Clancy, Archie Moore to name a few.
Never heard him speak, but AJ Liebling wrote about the game on a high level — not so much in a technical sense but conveying a lot about the sociology and psychology around a fight or boxing event in a very accessible and humorous way. Nobody conveyed the characters around the sport he way AJ did.
Cus certainly made the sweet science sound mystical- Never a dull time with the great eccentric trainer.
