Some great observations by the greatest chronicler of the 1989 anti-communist revolutions, Timothy Garton Ash, in The New York Review of Books:
During the first half of 1989, the new US administration of George H.W. Bush was extremely reticent in its response both to Gorbachev and to the changes being pushed forward by a combination of reform communists and dissidents in Poland and Hungary. What we have learned from the Soviet and East European archives confirms that Washington's assessment was, in fact, far too skeptical. (In one of several excellent scholarly essays in the volume edited by Jeffrey Engel, Melvyn P. Leffler notes how then Defense Secretary Dick Cheney suggested that Gorbachev's policies "may be a temporary aberration in the behavior of our foremost adversary.") Nor did Bush set much store by bearded dissidents who looked like something out of Berkeley in the 1960s. Victor Sebestyen, in a book full of sharp snapshots and crisp narrative, has a well-sourced account of the President meeting with the leading Hungarian dissident János Kis in Budapest in July 1989, and subsequently telling aides, "These really aren't the right guys to be running the place." Much better to stick with a preppy reform communist.
Yet even though Washington's cautious attitude partly resulted from a misassessment, this was actually the best possible position it could have taken. This time around, unlike in 1956, no one in Moscow could suggest with even a jot of plausibility that the United States was stirring the cauldron in Eastern Europe. On the contrary, Bush personally urged General Wojciech Jaruzelski to run for Polish president, as a guarantor of stability, and he was obsessed with doing nothing that could derail Gorbachev. Sarotte suggests that American restraint made it easier for the Soviet Union, too, to step back and let events unfold on the ground in East-Central Europe. With some exaggeration, one might say that Washington got it right because it got it wrong.
To give credit where it is due: in the last months of 1989, especially after the fall of the Wall, and throughout 1990, this initial superabundance of caution turned into a combination of entirely deliberate restraint ("don't dance on the Wall!" was the injunction heard in the corridors of the White House and the State Department) and some quite impressive statecraft in support of Helmut Kohl's drive for German unification on Western terms. But for the decisive nine months, from the beginning of Poland's roundtable talks in February to the fall of the Wall in November, the United States' contribution lay mainly in what it did not do. […]
It is perhaps a characteristic of superpowers that they think they make history. Big events must surely be made by big powers. Yet in the nine months that gave birth to a new world, from February to November 1989, the United States and the Soviet Union were largely passive midwives. They made history by what they did not do. And both giants stood back partly because they underestimated the significance of things being done by little people in little countries.
I'll never forget just how baffled H.W. Bush seemed by events back then. He gave a speech to 100,000 people on Wenceslas Square in Prague on the one-year anniversary of the Velvet Revolution that was almost a masterpiece of mangled cues, from botching the pronunciation of "Vaclav," to piping in Civil War music at a time when the Czechoslovak Federation was beginning to fracture, to prattling on about God to one of the most atheistic countries on earth. Bush was advising Yugoslavia to stay together long after the first shots of that breakup had already been fired, and focusing most of his diplomatic attention (and even Central Europe speechifying) on putting together a coalition for the Gulf War. It's a pretty weird feeling when events are hurtling much, much faster than the participants, let alone superpowers, can comprehend or control.