WHERE IS THE MONEY COMING FROM? Is development aid invested in Africa a beacon of hope or an example of ‘Afro-pessimism’?[1] Today, Africa finds itself at a crucial juncture of development with a growing population, burgeoning market, expanding resource base, and, more importantly, a willingness to orchestrate a future driven by an African development vision. The vital caveat in this discussion is that Africa’s bright future is not merely privy to African nation-states or its citizens but finds itself within policy briefs of Western countries, budgets of philanthropic organizations, and audit reports of development partners. Rooted within the call to decolonize knowledge, systems, and universities, there is a growing agreement that philanthropy in Africa must be decolonized (Krauss, 2018). Development aid must be unpacked to engage with colonial and hegemonic institutions, power, and dynamics that operate or structure it. Development practitioners engaging with African development, its multiple futures, and stakes highlight essential considerations to critically analyze the colonial basis of aid invested in Africa. Firstly, scholars question the characterization of aid as a free handout or a generous investment for improving ‘unhopeful’ lives. The reality is that support in Africa is conditional, directed at strategic interest to gain influence, partners, workers, market, and resources, to name a few (Iweala, 2017). The second complexity is the investment history and the ideology that propels it. Historically, Africans were ‘helped’ to ‘liberate’ and ‘save’ them by displaying poverty and violence as the continent’s reality (Goris & Magendane, 2021). This ideological basis laid the ground for humanitarian interventions and logic wherein infrastructure was built to reinforce colonial purposes, exposing the lasting overlap between aid and colonialism in its operations. Colonialism extends far beyond the occupation of ‘territory’ by force (Banerjee & Shriram, 2022). Within this context, the call for decolonization means that acts of generosity cannot absolve individuals (read philanthropists) from accountability for their actions. Thirdly, the sector’s expected investment outcome from ‘capacity building’ to ‘capacity bridging’ by rooting philanthropy in social justice, equality, representation, and empowerment is a recurring debate (Peace Direct et al., 2023). An often-quoted argument is that humanitarianism historically disabled African states to not invest in their development or generate wealth for development purposes (Goris, 2021). Does the call for decolonization imply a complete withdrawal of humanitarian aid to help states find their grounding, and is a disconnected approach the solution to incoming foreign aid in an interconnected world (Krauss, 2018)? While problematizing the basis of philanthropy in Africa, this paper also engages with possible policy solutions that, rather than absolving philanthropists of responsibility, look at involving Africans as equal partners within the aid ecosystem.