This research paper examines the evolution of digital leadership as portrayed in The New York Times articles from 2020 to 2022, addressing the growing complexities and strategic roles influenced by digital technologies. The study identifies critical issues in digital leadership, including ethical dilemmas, cybersecurity threats, and the digital divide, which pose significant challenges to effective digital governance and strategy implementation. The objectives of this research were to uncover and analyze the prevailing themes and sentiments associated with digital leadership using advanced Natural Language Processing (NLP) and Artificial Intelligence (AI) tools, specifically Nvivo and Monkeylearn. Our methodology involved a content and sentiment analysis of 318 articles, chosen from an initial pool of 387, resulting in a dataset of 2,428 content blocks. This analysis enabled the identification of major themes: Digital Transformation, Innovation, Remote Working, and Cybersecurity. The results indicate that ‘Digital Transformation’ and ‘Innovation’ were the most prominent themes, with significant discussions around ‘technology adoption’ and ‘AI’. The sentiment analysis quantitatively underscores the public discourse, revealing that 60% of the analyzed content carried a positive tone, reflecting an optimistic view towards digital advancements. Conversely, 29% expressed negative sentiments, emphasizing the urgent need to address associated risks. Significantly, the statistical evaluation of theme prevalence and sentiment ratios provides a nuanced understanding of the digital leadership landscape, suggesting a critical balance is necessary between leveraging opportunities and mitigating risks. These findings contribute to the theoretical and practical discussions on digital leadership by highlighting the importance of strategic adaptability and ethical considerations in shaping policies that are both inclusive and effective. In conclusion, this study offers a detailed, numerical insight into the complexities of digital leadership, providing valuable evidence for policymakers and business leaders aiming to navigate the challenges and opportunities presented by digitalization.