During the thirty years of Lee Kuan Yew's premiership of Singapore, he spectacularly transformed the island into a tightly controlled corporatist state that mirrored his own beliefs about the nature of society, especially on matters of race, language, democracy and welfare. His successor has tried to make his own mark on Singapore, but his early experiences left lingering doubts about his capacity to introduce fundamental changes. Partly as a result of Prime Minister Goh Chok Tong's failure to differentiate himself from Lee in his dealings with oppositions there has been a popular tendency to see his reforms as being cosmetic or at most purely functional. Such assessments, however, underplay the radical nature of some of Goh's initiatives. This does not refer to his efforts to create a public space for non-confrontational civil society, but to the weakening of the PAP's hard line against 'welfarism' and changes to its approach to matters of race and ethnicity. These developments beg an important question: what are the parameters of likely change in Singapore? Or to put it another way: where are the 'out-of-bounds' (OB) markers within Cabinet? This paper will try to answer these questions by considering current reforms in an historical context. It distinguishes between Lee Kuan Yew's personal legacy, and the core ideological premises of the regime, and argues that some of the reforms being implemented by Gob are significant challenges to the former, but are well within the bounds of the latter.