Markus’s study of IT politics has been influential for the IT implementation literature since the 1980s. However, mistakes of the top-down implementation approach could still be easily found in many organizations. Derived from Markus’s notion of interaction theory and Drucker’s work on knowledge workers, this paper illustrates a LMS (learning management systems) implementation case that evolves from such traditional top-down approach. Based on a chronological analysis, the case study narrates how IT politics was shaped in a context where most stakeholders were highly skillful knowledge workers whose academic autonomy was largely overlooked. Reflective discussion suggests how the implementation process might have been better managed. Evidently, even decades after Markus’s and Drucker’s influential work, history still repeated itself and IT politics continued to provide lessons for contemporary IT managers and researchers. Future strategy and implementation approach for campus IT projects and LMS implementation in particular are recommended.