Rabbi Avi Weiss can be a bit of a controversial figure that very few people, I think, take seriously, for two major reasons, that I think may be related.
The first is by reputation. He’s not known for being a למדן – he’s not known for being a learner; not known for being a תלמיד חכם, which I find very unfortunate. Having heard him numerous times – my grandparents go to his synagogue in Riverdale often – and other interactions, I can tell you that Rabbi Weiss is a lot more knowledgeable and a lot smarter than just about everyone gives him credit for. It might not come across because he might act like a Carlebachian hippie, but there’s a great deal of substance under there that’s very easy to overlook.
The other issue that I think comes up is that leads people to make either irresponsible or just flat-out wrong assessments is they focus too much on conclusions; by which I mean What is the conclusion? What is the statement that Rabbi Weiss says? If you agree with it, you agree with what he’s trying to accomplish: “Oh, how great, how courageous he is”. And if you’re predisposed to not liking what he says: “The guy’s a כופר – he’s a heretic, and he’s not really Orthodox”. And neither one of these responses addresses the issue of method; meaning, you could be right, but for wrong reasons, you could also be right for wrong reasons. But no one actually addresses the arguments on their merits. People get so worked up in the emotional reaction of “Do we like what he says or do we dislike what he says?” And I think that, too, is unfortunate, because I think there is a system here and I think it’s worth unpacking.
Rabbi Josh Yuter, “Halakhic Process 25: Open Orthodoxy“, Yutopia Podcast #119 (27 October 2013).