It is election season again, and across the state local teachers’ unions are campaigning for the candidates featured on their Apple Ballot, which they will distribute to large numbers of voters this November. The Apple Ballot enjoys a somewhat privileged place in the minds of Maryland’s voters because of its claims to represent the views of teachers. But the union’s interests do not always coincide with the public’s interest in improving education, or even the interests of the teachers themselves. Just as the union issues questionnaires to political candidates prior to endorsing them, this paper in turn asks some questions of the unions. This should not be construed as “teacher bashing,” “anti-union,” or “anti-public education,” as unions sometimes label those who offer alternatives to their policies, but rather as a critical examination of whether teacher unionization and the policies unions support have benefited teachers and the general public. It is healthy for any organization—especially one that claims to have the public’s best interests at heart—to be challenged from time to time. The Maryland State Teachers Association and its affiliates have been asking candidates questions for decades. The time has come to ask them some questions as well.