In Trinidad and Tobago, cronyism and nepotism have long been pervasive issues, deeply embedded in both the private and public sectors. The practice of leveraging personal connections to secure opportunities has become a defining characteristic of the nation’s professional and political landscape. This ‘contactocracy,’ as it is often termed, perpetuates a cycle where governance and societal progress are hindered by favoritism rather than meritocracy. A recent revelation by Legal Affairs Minister Saddam Hosein has brought this issue to the forefront. Hosein disclosed that a well-known blogger received payments exceeding $3.3 million between 2017 and 2025 through a company registered in her name. Despite the company’s claim of ‘over 25 years of experience in communications and media consultancy,’ it had only been operational for three weeks when it was awarded the contract by the Ministry of Finance in 2017. The blogger defended her eligibility, asserting her competence as a digital marketing strategist. While government contracts with private entities are not inherently problematic, the lack of transparency and merit-based selection processes raises significant concerns. The absence of a verifiable digital footprint for the work allegedly performed further fuels skepticism. This case underscores a broader issue: the prioritization of connections over qualifications in state contracts. Such practices not only erode public trust but also perpetuate inefficiencies and inequities in governance. The narrative of ‘eat-ah-food’—a colloquial term for benefiting from state resources—often overshadows legitimate contributions, as seen in the author’s own experiences. Despite delivering impactful campaigns for state organizations like Cepep and the Ministry of Health, the author faced accusations of cronyism when appointed to the EMA board. This highlights the politicization of public service and the need for systemic reform to ensure fairness and accountability in governance.