This chapter provides a rare practitioner’s insight into the field of international trade by someone who has been at the centre of many of the most important international trade negotiations over decades, including the final successful ‘Round’ of multilateral negotiations (the ‘Uruguay Round’) as his country’s chief negotiator, and as the chair of two technically and politically complex negotiations (‘Rules’ and ‘Agriculture negotiating groups’) in the ill-fated ‘Doha Development Agenda’. He was also the author of the strategy paper that launched what became TPP, now ‘Comprehensive and Progressive’ TPP. As both a senior international negotiator, a Trade Minister and Ambassador to both the WTO and the United States, he has seen both success and failure. Some political lessons and pertinent observations will be of interest to any reader wanting such an ‘insider’s’ perspective.