Against that backdrop of recent history, Trump will sit down with Mexican President Enrique Peña Nieto on Wednesday. But what does either side stand to gain from it?
Despite their geographic proximity, Mexico and the United States have a political relationship that could be better described as "complex" rather than "close." Mexico prizes its independent approach to international relations, and has historically diverged from the United States on counternarcotics and trade policies, among others.
But beneath this story lies another: The neighboring countries have steadily increased their security cooperation in recent years, while their economies have become tightly interwoven.
Like the political relationship between the two, Mexican views of the United States are also complicated. Since 2013, Chatham House has been running a research project examining how elites in different regions of the world view the United States. For the last 18 months I have been collecting and analyzing views from Latin American elites. The results of the project will be published next week.
This research found that members of Mexico's elite are acutely aware of the history of American intervention in Mexico. They also tend to take a dim view of American policies on drugs and guns, blaming them for contributing to the wave of violence perpetrated by powerful criminal organizations since 2006.
But at the same time, there is a deep sense of familiarity between the two countries. Mexicans tend to be well acquainted with American politics and culture. Those who talked to me as part of our research often spoke of the United States in familial tones. Their frustrations with American policy were generally couched in terms of disappointment and frustration rather than fear or contempt.
So the relationship, while far from perfect, is quite good for Americans and Mexicans alike. And both countries need it to remain so, because a political rift could easily affect the pair's economic relationship and security cooperation, with unpredictable but almost certainly negative ramifications.
Donald Trump's approach to Mexico has struck at the positive aspects of that perception while reinforcing the negative. Whether or not his promise to build a wall on the border is ever fulfilled, his starkly zero-sum view of the relationship between the two reinforces perceptions of the United States as deeply uninterested in collaboration or the mutual benefits that might come with it: for example Mexico's recently renewed willingness to extradite major drug trafficking figures to the United States, ensuring they're more fully removed from operational control of their organizations.
Unfortunately, to a large extent, the damage has already been done. For someone to get so far in American politics by describing Mexico and Mexicans in uniformly negative terms will reverberate through bilateral relations for years. Even if Hillary Clinton wins, anti-Mexican sentiment in the United States is unlikely to diminish, and Mexico has now seen just how extensive that sentiment is.
So, in bringing Trump to Mexico City, Peña Nieto is walking a fine line. His handling of domestic security issues and the emergence of various personal scandals, along with generally sluggish economic growth, have endangered his party's chances in the 2018 election. Like all Mexican presidents, he is limited to just one term, but being able to hand power to another leader from the same party will go a long way to securing his political legacy.
So why is he doing it? Taken at face value, this is an opportunity for Peña Nieto to turn the page on his troubles. Trump is wildly unpopular in Mexico. Visibly taking a hard line with him might boost the Mexican President's popularity.
Meanwhile, Trump may be counting on a frosty reception from the Mexican government to argue to skeptical voters back home that his hard-line approach is justified, or that his business negotiating tactics are applicable to international relations. That is a high-risk approach, to put it mildly, but it is not entirely out of the question that such a gamble could reinforce his appeal to at least some parts of the electorate.
Peña Nieto's team has likely made the calculation that Hillary Clinton is a safe bet in November. But even if that's right, he may still be perceived as having tried to intervene in an (already complicated and unpredictable) US election. So while both Peña Nieto and Trump might reap transient political benefits from their brief summit, it will only further complicate Mexican/US dealings in the longer term.