How does the western media assess the inclusion of Poland in a larger Western European community? The data reflects the media's assessment that Germany and France, in particular, perceive Poland as insolent, contrary and hubristic, while in general, the Poles view themselves as second-class citizens within the European Union. In addition to the media's perspective however, this paper explores Poland's complex relations with Europe and the United States through a rich historical context that presents Poland's dilemma as it strives to be an equal and respected member of the EU and NATO while balancing its strong relationship with the US. For the purposes of this research, this paper entails qualitative and quantitative, content analysis of eleven articles published in each of the four selected media sources which include the Economist, the New York Times, CNN and the BBC after March 12, 1999, the date of Poland's induction to NATO. This research concludes that Poland is fundamentally European, but that it possesses exceptionally close cultural and historical ties with the United States that helps the reader to understand why it is that the French and Germans have some reservations regarding Poland's expanding role in NATO and the EU.