Last September’s Chicago teachers’ strike raises critical strategic questions for all progressives and socialists seeking to resist the relentless neoliberal austerity attacks against working people and their communities.… [While in many ways it was a success,] it must be frankly recognized that the CTU’s contract campaign, which culminated in the seven day strike, fell short of achieving its ambitious goals at the contract table. In particular, it was unable to: significantly slow the mayor’s crusade to close scores of schools; halt district funding for mostly non-union, privately run charter schools; stop the lengthening of the school day and year without adequate employee compensation; or prevent the establishment of a teacher evaluation system based to an important degree on unreliable student scores on standardized tests. These less-than-optimal results deserve serious analysis, especially in light of the local’s herculean efforts to transform CTU from a classic, conservative business union to a progressive, even radical, organizing union. Could the strike have achieved more if other strategic choices had been made? Were some demands simply unwinnable?