I analyze the causes of highly skilled emigration, otherwise known as Brain Drain, in the three countries of the Southern Cone: Argentina, Chile, and Uruguay. These three upper-middle income countries have similarities in culture and level of economic development, which serve as the grounds for an effective comparison. I find that Chile has been especially successful in combatting Brain Drain while Argentina has been especially unsuccessful. Uruguay has been neither successful nor unsuccessful, but still faces a significant Brain Drain problem due to uncontrollable factors (for example, its small population). I recommend that the Argentine and Uruguayan governments broaden their current anti-Brain Drain policies, with the aims of (a) reducing the emigration rate of highly skilled workers, (b) promoting return migration among highly skilled workers in all sectors, and (c) maintaining connections with members of their respective diasporas. I find that the policies that directly address the issue of highly skilled migration are not necessarily the most effective. Thus, I emphasize potential policies to reduce Brain Drain that address economic issues that indirectly cause Brain Drain, in addition to addressing migration directly.