<p>In the first decade of the 21st century, Bhutan and Tonga enacted reforms which took executive power away from the monarch and placed it the hands of an elected government. Conversely, Thailand and Nepal have faltered in their trajectory towards democracy. Thailand is stuck in a cycle of repression, popular protest, limited democracy, renewed military takeover, and constitutional revision to allow a controlled “democracy.” Nepal has broken out of a similar cycle (although without military rule), at the cost of abolishing its monarchy. This thesis looks at factors, including the monarchy’s role, which contributed to the different outcomes. The study questions Huntington’s theory of the modernising monarch’s dilemma (fear that reform would do the monarch out of a job), and suggests that, on the contrary, a democratising monarch is more likely to retain the throne, albeit with reduced power. This comparative qualitative study is based on research into primary and secondary sources, plus interviews. The thesis found that in Bhutan and Tonga strong leadership of democratisation by Kings Jigme Singye and George V greatly favoured a successful democratic transition. In both Thailand and Nepal, monarchs Bhumibol and Gyanendra resisted a democratic bargain, seeking instead to retain or regain political power, in a context where popular mobilisation and the role of the military were significant in both countries, but with considerable differences. Contrary to Huntington’s theory, monarchs in Thailand and Nepal, in seeking to avoid loss of political ascendancy suffered the opposite, although to differing degrees (one monarchy was disestablished while the other first gained ground but ultimately ceded ground to the military, reversing a pattern of monarchical dominance in the partnership). The thesis concluded that, against a historical background of special status for the monarch as symbol of national unity, and even in the face of unpromising structural conditions, monarchs who used their charisma to promote and lead a move to democracy were a critical factor in whether a transition would be successful, while securing the future of the monarchy for their heirs. Conversely, monarchs who formed strategic alliances with elite groups seeking to preserve their ascendancy, including the military, provided an excuse to autocratic groups for resisting democracy and risked either a reversion to (or retention of) autocratic rule or a transition to a democracy that did not include a place for the monarchy.</p>