The tension at the heart of pension politics is the incentive to satisfy today's claimants in the here-and-now at the expense of long-term concerns. Rules and auditing standards are intended to tame this kind of short-sighted behavior in the private sector. In the public sector, the primary safeguard is the hope that public officials will not be unduly tempted by short-term considerations or influential constituencies. Teacher pensions, in particular, pose two challenges. The first challenge is that political incentives invite "irresponsible fiscal stewardship," as public officials make outsized commitments to employees. The second is that incentives "hinder modernization," as policymakers avoid the politically perilous task of altering plans ill-suited to attracting talent in the contemporary labor market. The alignment of the political stars has helped states and localities to address the first challenge, but there is little evidence of a willingness to tackle the second. This paper illustrates those dynamics through discussions of fiscal crises in New Jersey, Oregon, and San Diego and the way in which those crises created opportunities for addressing funding shortfalls. It closes by suggesting several political strategies that could make pension challenges more tractable and encourages public officials and especially state legislators to be more responsible fiscal stewards or to revisit anachronistic retirement systems in pursuit of improved teacher quality. (Contains 129 endnotes and 1 figure.) [This paper was originally prepared for the second annual conference at the National Center for Performance Incentives in February 2009.]