30 for 30 wasn't a groundbreaking idea. If it wasn't him, someone else would've came up with a documentary series. It's not like he came up with the actual content for the docs. There was probably numerous interns or low level guys who offered that idea numerous times and had it thrown out or overlooked because they didn't have any cache. If Simmons was brilliant he would have reinvented himself already. All this talk about HBO blah blah blah and you can only find him on iTunes or Instagram.
Grantland was decent because of a few writers (Jonathan Abrams really). Most of it was corny, wordy, hipster, contrarian crap. You couldn't pay me to find or read any of the full time writers that were on there now.
As far as this poll, I'd say Cowherd, Simmons, Beadle, Deadspin as a group are the most annoying. But they have next to no reach these days so they don't annoy me at all. Stephen A just has a bigger platform (and he's rich and black) so he was gonna win