The first time I heard about Barry Silbert was during the block size wars, I think. I seem to remember him being prominent in the so-called New York agreement, but please correct me if I'm wrong. (Not that it really matters any more, btw.)
Anyway, as reported by several news outlets, he resigned from Grayscale earlier this week and it appears they (Grayscale) rushed to amend their bitcoin ETF application as a result.
The link I posted speculates it may have been a "strategic move". What do you think?