Media in Europe have undergone profound transformations. These changes involve structural transformation (global trends, the role of politics, EU, etc.); sectoral transformation (e.g., deriving from within the media domain); and the role of particular individuals (such as media moguls). In this respect, there is a lack of comparative studies which systematically explore the relations between these three dimensions in European transformative processes. To add new insights to existing knowledge about media systems across parts of Northern, Eastern and Central Europe, the purpose is to compare understandings of media transformation during the last two decades from a structural, sectoral and individual perspective. Eighty interviews were conducted with media experts from Austria, Bulgaria, Czechia, Latvia and Sweden. The results demonstrate detailed examples of not only an emerging commonality, with similar changes across Europe, but also consistent differences concerning areas such as the role of history, the pandemic and geopolitical tensions.