President Barack Obama's 2014 opening with Cuba helped funnel American travel dollars into military-linked tourism conglomerates even as state security agents waged a fierce crackdown on dissent.

The rapprochement also poured hundreds of millions in U.S. spending into privately owned businesses on the island, supercharging the growth of an entrepreneurial middle-class independent of the communist state. It opened a new market for American corporations, with JetBlue and American Airlines operating from gleaming new Havana offices and tens of thousands of private bed-and-breakfasts listed on Airbnb.

Internet access became an affordable reality for hundreds of thousands of Cubans as President Raul Castro met a pledge to Obama and opened nearly 400 public Wi-Fi access points across the country. Meanwhile, longtime enemies separated by 90 miles of ocean struck agreements to cooperate on issues ranging from human trafficking to oil spills.