Research SummaryDrawing on institutional economics and the legitimacy‐based view of political risk, we investigate the factors determining the realization of cross‐border investments by sovereign wealth funds (SWFs), whose investments often suffer from a lack of legitimacy in host countries. Using matching models on all the realized and potential investments, we find that investments are more likely to materialize when the SWF home country and the host country enjoy cordial political relations or are involved in a trade agreement. Contrary to the theoretical predictions, SWF politicization does not per se represent an impediment to the realization of investments. Rather, it has a negative effect on the likelihood of an investment's realization only in the presence of trade agreements.Managerial SummaryA recent trend in the global economy is the increasing cross‐border investment activity undertaken by sovereign wealth funds (SWFs), large investment vehicles where financial and political goals often co‐exist. On the grounds of possible financial or political destabilization, SWFs' cross‐border investments attract scrutiny and suspicion in host countries, hindering their realization. We analyze SWF‐ and country‐level factors that may determine the successful realization of SWFs' cross‐border acquisitions. We suggest that managers ex ante select target firms and host countries by considering their fund's governance and degree of independence from home‐country politics in interaction with bilateral (home‐host country) political and economic relations, so as to secure legitimacy for their investments and maximize the chances that cross‐border investment strategies may materialize.