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Do you know what extension he's on? sma fittor
  By 'not progressive enough', he means there is not enough federal control over every aspect of the local schools for his kids. Probably an inside joke alluding not just the political beliefs he supports but the perks he gains for his children from them. At his national security clearance level he can enroll his kids in deep government schools where they learn to spy, lie, and influence people. His children will surely be groomed to play an important role in the overall 'progressive' plan.