Lech Wałęsa, an electrician from Gdańsk, emerged as one of the most influential figures in Poland’s transition from communism to democracy. As the leader of the Solidarity movement, he negotiated the first peaceful transfer of power in Eastern Europe, challenging a seemingly unshakable communist regime. His leadership during the 1980 Gdańsk Agreement and the 1989 Round Table negotiations exemplifies the power of strategic negotiation, coalition-building, and resilience. This chapter explores Wałęsa’s negotiation strategies, highlighting his ability to unify diverse opposition groups, leverage international support, and engage in pragmatic, step-by-step reforms. From leading strikes at the Gdańsk Shipyard to becoming Poland’s first democratically elected president, Wałęsa’s journey provides critical insights into negotiation under extreme power asymmetry. His legacy offers valuable lessons on the role of persistence, strategic compromise, and moral authority in political transformation.