The craziest day the Cup has ever lived in its history is without a single doubt when the Chicago Syndicate won it for the first time in franchise history. It was the victory parade day in Chicago and everyone was celebrating and getting as wasted as they had ever been in their entire life. JUST (who was still JURT back then) had poutine flown down from his little hometown in Quebec to eat some from the Cup as soon as possible. It was fucking terrible and incredibly soogy (what was he expecting) and he retched in the cup in front of all these people while Gunnar held his hair back for him (how sweet, what a good friend, thought JURT). Then Corey decided to order a paraglider and started throwing the cup from buildings to see where it would land, after cleaning it of course. Then at the end of the night Matty waterboarded a thug who owed him money directly inside the bowl of the cup.