A few days ago, Russia flew a small number of service personal into Venezuela. What he understood, perhaps from his intervention in Syria, is that while the US might use military force in "shit-hole" countries, it won't take action that might harm Russian soldiers and cause a dangerous escalation.
Putin is daring Trump to act. While the US president has said all options are on the table, Putin's move effectively removes a military option from those the President has to work with. Now that's some pretty good strategizing.
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