Trinidad has the distinction of contributing the highest number of recruits per capita to the cause of notorious 'Islamic State'. The case of Trinidad and Tobago (usually abbreviated 'Trinidad') makes for an interesting study as on the face of it, a well-integrated Muslim population, a strong welfare state and an absence of political persecution on any religious or racial basis should not provide fertile recruiting ground for Jihadist ideology. However, the converse is most certainly the case as not only is attraction to such extremist causes growing but the numbers of Trinidadian nationals willing to fight for IS is also increasing. What is happening in Trinidad is symptomatic of a broader problem as Jihadi groups have widened their reach where apparently unconnected groups can now ally with the ideology and resource bases of better known groups without formally being part of them. The flirtation with Islamist ideology on Trinidad dates back many years and through a combination of incompetence, political naiveté and unfortunate compromises. Indeed, the country faced the only Islamist coup in the entire Latin America - Caribbean region and the hemisphere.