Most negotiation professors tend to focus on teaching problem-solving techniques to achieve long term goals, build a relationship with the counterpart, and maintain a positive reputation. How do these assumptions get taught (and challenged) by a president who appears to negotiate with exactly the opposite strategy? By urging students to understand Trump’s audience (his base), his time frame (short), and his preferred reputation (bully), we can then discuss the impact of Trump’s negotiation strategies and who exactly will be paying the price for his brinkmanship and bullying reputation.