Hmm, how would I want the Chicago Syndicate to make it to the Challenge Cup finals and eventually win it all? Well, what would make the run more extreme than any other cup run we have seen would be a completely new playoff format. We literally take all of the non Chicago teams in the SHL and pick them out in random order. Then, every team plays a seven game series against the Syndicate in order of selection. Chicago would have to win every single series against every other team in the SHL in order to win the cup. However, if just one team managed to beat the Syndicate in a seven game series, that team would immediately win the Challenge Cup (better hope your team comes up in the beginning of the order, I guess?) And then further, since this is literally just my fan fiction, Chicago would go on to sweep literally every team in the SHL in order to win the most contested Challenge cup ever.