I wouldn't say I feel bad for ESPN, but Deadspin helped foster this anti-ESPN community that pounces on any weakness they have. They can't partner (or hire) anyone with skeletons in their closet, otherwise the trolls will attack and hold them up as hypocrites.
So, that kind of traps them into playing it safe and not really evolving as a content provider.
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They should really just spin off one of their channels into a new property (and don't meddle with it) and try all their weird shit there.