This chapter discusses the circumstances of Ginsberg’s arrival and deportation from Czechoslovakia in 1965. Although it is often thought otherwise, Ginsberg did in fact have long-formed plans to travel behind the Iron Curtain, and his expulsion from Cuba only expedited, rather than facilitated, his arrival to Europe. During his stay in Czechoslovakia, Ginsberg had the opportunity to look behind the façade of the Communist Party and observed firsthand that Czechoslovaks lived in an oppressive regime they increasingly tried to challenge through various means, one of them being the publication and performance of Beat poetry. However, he underestimated the surveillance practices of the regime, which only intensified after Ginsberg was elected the King of May in front of a 100,000-strong crowd during May Day celebrations. Ultimately, his often frank discussion of his views and experiences not only placed several of his associates in danger, but also led to his deportation from the country.