My hand to God, the most likely explanation I can think of is that maybe Trump was watching Escape From Alcatraz on Air Force One and it sent him into yet another reverie about the America of his youth. Remember when we sent convicts to Alcatraz? Remember when we shot movies in U.S. locations like Alcatraz? Why don't we do that anymore? So he decided in that moment that we should do it again. The nice thing about being king in a country whose legislature has effectively dissolved itself is that you can tap out a few sentences on your phone and know that the world will receive them like royal decrees.
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