During the 2012 U.S. Presidential campaign, President Obama turned some heads by stating “If you’ve got a business – you didn’t build that”. His opponents argued that this was an attack on private enterprise (with “that” referring to business), while his supporters and fact-checking organizations maintained that “that” referred to what Obama was talking about previously (U.S. infrastructure) and represented his political-economic plan of an increased interlacing of private business with government investment. I argue, from a relevance-theoretic perspective, that both interpretations follow from differing contextual assumptions on the part of the audience. In this sense, the role of contextual assumptions in utterance interpretation is highlighted – different contextual assumptions lead to different cognitive effects if the utterance leaves room for more than one interpretation. Combined with a highly polarized U.S. political arena, where participants pounce on their opponent’s every possible miscue, all the ingredients for misunderstanding are present.