This contextual biblical reading of Luke 18:18–30 (the encounter between Jesus and the rich ruler) foregrounds the political and economic context of the Pacific Island Countries and Territories (PICTs). The reading carefully explores the biblical text’s context, an exploration that includes looking at specific intertextual sources and engaging scholars from Asian and African contexts. The reading is then applied to a contextual biblical approach to poverty in Samoan society. The contextual biblical reading resituates the ruler in the Lukan narrative within the context of the household and the institutional constraints of its ecological environment. The theoretical framework for the contextual biblical reading is guided by the Samoan proverb seu le manu ae taga’i ile galu (catch the bird and watch the wave), symbolizing responsibility and restraint in biblical interpretation. At the end of the contextual biblical reading, a new way of reading Luke is presented, and three broad propositions are suggested for further consideration. The main argument of this deep contextual reading of the Lukan passage is that the rich ruler offers a different form of “following,” which is possible by “living responsibly with wealth.”