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Well, since this Pope does not travel as widely as the previous Pope, his choices are arguably more strategically considered. Mexico is the Spanish-speaking behemoth in the Western Hemisphere (Portuguese-speaking Brazil is the overall behemoth and commonly noted as the the country with the largest population of Catholics in the world). Latin America as a whole contains almost half of all Catholics worldwide.
Another strategic angle for us in the U.S. is that Hispanic Catholics, especially those of Mexican origin, are transforming the Church in the U.S. In contrast to, say France, where a diminishing number of French Catholics exists with a large influx of Muslims, in the U.S., the situation is one in which the immigrant influx actually bolsters the Catholic presence. Thus, a visit to Mexico is also an indirect visit to the Church in the U.S. because of the large role Mexican Catholics now play in the demographics of the Church in the U.S.
As to Cuba, we see the priority of re-evangelization in the wake of a looming and inevitable post-Communist reality. Sooner or later, there will no longer be a Communist dictatorship in Cuba. The transition is not only political but also cultural and religious. For decades now, Cuba has exported Communist ideology to the Caribbean, to Latin America, and even to Africa. The new Cuba may in the future be known for exporting Christian evangelists, both Catholic and Protestant, as its dynamic, entrepreneurial, and energetic population enjoys a newly found freedom in religious matters. Cuba's prime natural resource is its people and their dynamism--a resource that has now been muzzled for decades; but that is set to break out of its current bondage.