‘Membership Has Its Privileges’ (1987 – 1996), ‘My Life. My Card.’ (2004 – 2007) and ‘Realise the Potential’ (2009 – 2012) are just a few of the print ad-campaigns for the American Express cards that over the years have helped construct the sign value of its charge cards as ‘the cards of the rich and affluent'. By conducting a diachronic (focusing on the changes over time) poststructuralist textual analysis of a sample consisting of the three aforementioned print ad-campaigns, and using semiotics as my main theoretical framework, I explore the mechanisms and signs American Express uses in order to convey its cards as symbols of distinction and success. The research reveals that the company has used different approaches in order to appeal to its targets in the different periods of time to meet the goals of their marketing plans and adapt to new socio-economic realities. In the first campaign of the sample, by mainly using celebrities and their referent systems, the American Express cards are portrayed as the entrance keys to a selective club. In the second campaign, the company shows a different side of celebrities, distancing them from the glamorized ideal normally associated with the celebrity lifestyle. In this specific campaign, the American Express card is conveyed as an instrument that allows people to conciliate their busy professional lives with what really matters – their family lives. The last campaign of the sample has been deeply influenced by the digital revolution. In this latest period in time the company immerses itself in the new medium and allows the readers to create and print and/or share on Facebook their own personalized print ad, taking the relationship between advertising and the individual to a whole different level and also marking the introduction of the company into the digital/convergence era. At this point, the American Express card is portrayed as your card, which you can count on to help fulfill your wants and needs, whatever they might be. As confirmed by the results, advertising is a dynamic practice, which is constantly evolving and creating new methods of persuasion and adapting to new time frames and technologies.