Chapter 6 discusses how trust can emerge in the formal political sphere. Engaging with arguments for “political friendship” and “salutary hypocrisy,” this chapter shows that a division of labour between “principled pragmatists” and “principled purists” can counteract the institutionalized enmity problem. Principled pragmatists can develop a sense of reciprocity by engaging in some forms of hypocrisy and by striking compromises; this reciprocity can counteract the tendency for political actors to compete as enemies. Meanwhile, principled purists can more stubbornly refuse to compromise in order to keep principled pragmatists honest. There are times, however, when the distribution of principled pragmatists across mainstream parties is unbalanced, just as there are times when some (former) mainstream liberal democrats have forged enduring alliances with autocratic political actors. Accordingly, the chapter argues that in these circumstances, those who stand outside of these “unholy alliances” must embrace contestation and show that participation in these alliances is politically disadvantageous.