The SS officer was really an accountant in Florida, the man Dwight played against, and nobody had ever killed him. Dwight never fought, himself, just relayed orders from the tacticians he hired. The Florida accountant was his own tactician, and a stone killer to boot. When he won a campaign, which he usually did, Dwight lost money. That kind of gambling was illegal, and federally, but there were ways around that. Neither Dwight nor the accountant needed the money they won, or cared about what they lost, not really. Players like Flynne were paid on the basis of kills, and on how long they could survive in a given campaign.