If you follow U.S.-Latin American relations at all, you've seen the Cuba Twitter story. It is a story of breathtakingly poor judgment. Here's the key paragraph.
At its peak, the project drew in more than 40,000 Cubans to share news and exchange opinions. But its subscribers were never aware it was created by the U.S. government, or that American contractors were gathering their private data in the hope that it might be used for political purposes.
The U.S. government does not get it. These sorts of initiatives will fail because they will be found to have a connection to the U.S. government, which immediately produces the exact opposite response of what you want. It is entirely possible that the main result will be for Cubans to be more wary of using any social media, which reduces their chances of organizing.
I'm pretty much dumbfounded by the dumbness, though of course I shouldn't be because stupidity is the hallmark of U.S. policy toward Cuba. But now it will spill into Venezuela as well, where critics bring up USAID all the time. The likely truth is that whatever USAID is doing is dumb and will play into the Venezuelan government's hands but this story shows in black and white how Venezuelan concerns are entirely justified.
Nice job, President Obama!