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How hard could it be? I actually uttered those words when I first contemplated representing a Guantánamo prisoner. I am a civil rights attorney who works primarily on contingent fee cases, so—rightly or wrongly—I consider a lot of my practice to be pro bono. But for many years, I had never really delved into a formal pro bono project. All of that changed when I received an e-mail from the Chicago Council of Lawyers in 2005. It announced a luncheon discussing Guantánamo, the U.S. naval base in...