The study focuses on news reports relating to Malaysia's Prime Minister Abdullah Badawi and Singapore's Prime Minister Lee Hsien Loong, who were given extensive media coverage during the handover period. The transition of both premiers was considered an event as Abdullah's leadership style is viewed as different from his predecessor, while Lee's ascension is expected since he is the son of the first Prime Minister, Lee Kuan Yew. The investigation of the present study is undertaken using the analytic paradigm of Critical Discourse Analysis (CDA) employed by van Dijk (1996, 1998), Fairclough (1992a, 1995a, 1995b, 2003) and Fowler (1991). The analysis looks at a general characterization of the newspaper discourse, with a focus on particular discursive strategies (i.e. newspaper headlines, leads, captions under photographs; quotation patterns; over-lexicalisation) employed to conceal ideological meanings. A corpus of newspaper articles of a local daily, The Star, is examined on 100 days after Abdullah took office, and the three months leading to Lee's premiership. Results from the analyses illustrate how the representation of Abdullah and Lee as ‘Mr Nice Guy' and ‘Mr Mysterious Guy' respectively, are reinforced using the various discursive strategies mentioned above.