Not exactly a story challenge, but hey.
Four of my friends and I took on the Chairman on advanced mode in Rook City. And we weren't completely crushed.
So I'm pretty happy with myself. It was an exciting battle, and I want to try it again some time to win.
But here's the crazy part: we took down The Chairman first. Through a stunning use of Wrathful Retribution, we knocked him clean out of the game right after he flipped. I can't describe my delight when we pulled this off. It certainly helped kill his absurd buff he was giving the thugs.
Sadly, we fell to the power of the Operative and a large team of underbosses and thugs, but in my heart, it was still a mini-victory.
But if I had just gotten Jack Handle sooner (I was Fixer), I'm telling you, that game would have been very different. Possibly a victory.