Hong Kong and Taiwan score high on “rule or law” but diverge on democracy. The “one country, two systems” arrangement for Hong Kong, promising gradual progress toward democracy, and the happenstance of post-colonial Hong Kong’s inherited legality and non-democracy contrast with Taiwan’s concurrent democratization and rising rule of law. The contrasting cases offer potential lessons about the relationship between rule of law and democracy. Taiwan suggests a conventional liberal story: rule of law and democracy go hand in hand, through elective affinity or profound interdependence. If Hong Kong sustains legality without democratization, it challenges the universality of such claims. But if rule of law is eroding, or pressures for democracy persist, Hong Kong may help confirm the conventional wisdom. With its experience with full-fledged democracy and rule of law, Taiwan also provides a case study in another common claim: the inescapability of tensions between rule of law and democracy.