This study explores advertising dynamics within the print and digital press sectors in Southern European countries—France, Greece, Italy, Portugal, and Spain—between 2017 and 2023, using Hallin and Mancini’s Polarized Pluralist Model as classification. The research addresses three main questions: the factors influencing advertising expenditure, the primary revenue drivers in the press industry, and the comparative performance of digital versus print sectors in terms of revenue and readership. The study uses data sourced from Statista and employs descriptive statistics and Two-Stage Least Squares (2SLS) estimation models to analyze advertising expenditure and revenue dynamics. Our findings reveal that digital press revenue and readership significantly boost digital advertising expenditures, while print advertising relies heavily on print readership and faces challenges due to declining audience numbers. Additionally, the study highlights that digital press platforms are outperforming print media in both revenue and readership, reflecting a broader shift towards digital content consumption. The study also reveals a notable positive relationship between print press revenue and digital press revenue, suggesting that strong performance in print media can complement and support digital growth within the same media organizations.