History is messy. Neither proponents nor opponents of the Trump-Kim summit should feel confident that history is on their side. History reveals reasons for pessimism, optimism, and caution. Attempting to critically engage the history of these nuclear negotiations can help the United States narrow uncertainty, prepare for a long diplomatic process should one transpire, and perhaps learn some tactical lessons. Given the paucity of concrete data on Kim Jong Un and his decision-making, humility in analysis is warranted. Confident statements about what the North Korean leader seeks before he tells us are misplaced. North Korea’s nuclear program has advanced significantly since the last nuclear deals, but the two sides seem to be getting closer to a formula for a possible deal. Any deal — if one is indeed possible — is likely to involve difficult trade-offs for both sides. Experts can help illuminate public debate on the merits of these trade-offs, but elected leaders will ultimately need wisdom for the hard decisions ahead.