Weigel takes the Vatican to task for misunderstanding the role of the Church in dealing with Castro's dictatorship during the visit. I think Weigel is largely right.
A century and a half after the demise of the Papal States, many Italian curialists and more than a few Vatican diplomats still habitually think of the pope as the sovereign of a mid-sized European power, who deals with other political sovereigns according to the usual rules of the sovereignty game: thus Father Lombardi’s clumsy response to journalists at the end of the papal visit, asserting that Benedict XVI had to play by the established ground rules. But he doesn’t, and neither does any other 21st-century pope. Yes, the pope is a sovereign under international law. But his authority in world affairs does not derive from the fact that he is the master of 110 acres in the middle of Rome and issues his own stamps and coins. As John Paul II demonstrated, and as Benedict XVI has also shown in many of his major public addresses (including those in Cuba), contemporary papal power is a unique form of moral authority that comes from an unshakeable determination to speak the truth, even in the face of worldly power.
The Church's secular power, as Weigel explains earlier in the essay, is moral authority. She acts through word and sacrament. She teaches by explaining, and doing. Prudence is of course essential; there are many situations in which direct confrontation is counterproductive. John Paul had no armies with which to challenge the Polish communist junta. The revolution he wrought was spiritual, and in a decade the communist totalitarian edifice in Europe was dust.
I believe there were some missteps in Cuba-- situations in which the Church could have made her defense of human dignity and freedom more effective. The Pope meeting with dissidents, for example, as a condition of meeting (and being photographed with Castro) would have been one way to strengthen the pro-democracy and human rights forces in that island prison.
All said, much good was done. The Lord's message of hope and freedom was brought to the people of Cuba. Perhaps even more good could have been done.
Read Weigel's essay for a thoughtful reflection on the historic visit of the Pope to a sad land cursed with the only political form atheism has ever taken.