Countering terrorist ideologies is a task that relies exclusively on trust in an authority and the matching of incentives to individual needs for any success to be realized. Broad messaging campaigns undertaken by both physically and/or culturally removed authorities have little impact due to credibility problems and tendencies to over-generalize. This work, proposing that successful counter-ideology occurs at the level of the individual, constitutes a rational actor and game theoretic analysis of counter-ideology programs in Indonesia and Singapore, evaluating their unique, individually targeted approaches to the problem of terrorist detainee de-radicalization. A survey of the Al-Jemaah Al-Islamiyah (JI) terrorist group's cultural elements provides specific vulnerabilities which are available be used against the individual detainee's attraction to the JI ideology. While both programs rely upon the influence of an authority to de-radicalize prisoners, they achieve this goal through very different ways of targeting individual vulnerabilities, building trust, and administering incentives. In the end, establishing detainee trust in diverse authorities is shown to be plausible, as is using de-radicalized prisoners and the newly trusted authority to influence prisoners to give up at least portions of the ideology. The results are categorized with respect to design of future counter-ideology and de-radicalization programs.