As a smaller actor in world affairs, Singapore will feel the ups and downs in major power relations more than most. Singapore historically benefited from being a commercial conduit among major powers, even before its establishment as a nation-state. Acting as a successful middleman is predicated on a degree of major power accommodation that accepted the prioritization of absolute gains among major powers. Contending major powers could accept that rivals could accrue benefits, potentially even more benefits than themselves so long as they profited themselves. As US-PRC rivalries intensify, Washington and Beijing focus increasingly on relative gains which means they see advantages by the other as detrimental to themselves. Such conditions reduce the range of options for Singapore to “not choose” and work with both major powers. Singapore must now navigate these more complicated new circumstances, but policy inertia and the costs of adjustment may limit its ability to undertake such shifts. It may find itself simultaneously under pressure from both of today’s major powers as a result. Despite Singapore’s uniqueness, these are considerations that may similarly affect other smaller states that previously gained from more stable major power ties.