This chart comes from a September 27 Congressional Research Service report, by Peter Meyer, about U.S. aid to Latin America and the Caribbean, going through the 2024 appropriations request (which Congress hasn’t funded yet).
When you adjust for inflation, nothing comes close to the amount of U.S. assistance the region received in the 1960s, during the Alliance for Progress, an aid program the Kennedy Administration launched in large part to prevent other countries from turning to Communist revolution like Cuba did.
The next biggest peaks are the 2010 response to Haiti’s earthquake just as the Mérida Initiative aid package was getting underway in Mexico; the Reagan administration’s Cold-War funding of civil wars in Central America; the Plan Colombia years of the 2000s; the Central America strategy that the Obama administration started (and Trump did not continue) after a 2014 wave of child and family migration; and the onset of the Drug War in the late 1980s.
My own career started during that deep trough of assistance during the post-Cold War Clinton 1990s. (I graduated college in 1992 and grad school in 1994.) Ironically, it was right at the absolute nadir that I co-founded a project to monitor U.S. security assistance in the Americas. (The data from that project, going back to 1996, is still part of the Center for International Policy’s Security Assistance Monitor.)