Like the title says.
Would he live up to the anti-Communist iconography fashioned for him by right-wing Cold Warriors? Or would he remain essentially on the left, bitterly critical of Stalinist regimes but still commited to both socialism and anti-imperialism?
From reading his essays, it seems to me that he was still pretty hostile to western imperialism and capitalism, even after the Cold War got going. Would he eventually have come around to thinking that Soviet power was such a global meance, that support for neo-colonialist and quasi-fascist elements in the former colonies was justified?
Animal Farm is pretty clearly a straightforward takedown of Soviet Russia, but I think 1984 is a little more ambiguous, with the reader being meant to understand that Oceania is now suffering an existence as a Yankee imperial outpost. And some of his earlier essays(eg. Decline Of The English Murder, the various reviews of pulp magazines etc) show a marked tendency toward bewailing the penetration of American culture and thinking into the UK.