This paper deals with the evolving scenario in the Korean peninsula in the wake of the Summit between Kim Jong Un and Donald Trump in Singapore on June 12, 2018. The paper surveys the core foreign policy concerns of USA and North Korea on Korean Peninsula affairs, profiles the principal players in the negotiations drama that unfolded a little before the bilateral meeting of the two leaders   to argue that the Singapore summit marks a game changer in US-North Korea relationship. The paper positions its arguments in the light of the paradigm shift effected by Trump’s foreign policy doctrine that marginalizes traditional allies of the US and seeks an unusual  reconfiguration of the world political  order that is premised on a possible US-Saudi Arabia- Israel  alliance (with possibly Russia put in ) against the duo  viz, Iran and China . It is argued that both Kim Jong Un and Trump, through their unconventional diplomacy styles, are attempting to change the pre UN Sanctions status quo (that rests on endlessly repeated provocative and counter provocative actions)  to one of a finitely repeating game  with  the outcome could be a  maximin solution. In the years to follow one sees the Korean peninsula  gravitating towards a medium ‘double freeze’ solution than getting caught in an impasse between  best/worst solution for the parties concerned, viz Complete ,Verifiable Irreversible Disarmament (CVID)  for the US and ‘pre UN Sanction’ status quo for North Korea.