From the inception of this nation's history, presidents have offered pardons and commutations of sentences conditioned on a surprisingly wide array of conduct. Presidents have offered clemency on the condition that offenders refrain from alcohol, provide support for family members, leave the country, join the navy, drop claims against the United States, and restrict their travel or speech. By attaching conditions, presidents may protect the public or benefit it in other ways. Although such pardons may advantage society, imposing conditions may restrict the constitutional rights of offenders. In order to escape the harsh confines of prison, offenders may have little choice but to accept restraints on their exercise of constitutionally protected freedoms. Moreover, exercise of conditional pardons may permit presidents to accomplish objectives that they could not otherwise attain. As an example, presidents can commute sentences of a particular class of offenders conditioned on supervised release or parole even if Congress has rejected such penological alternatives. Nevertheless, this Article argues that exercise of the pardon power generally should remain vested in the president's discretion, checked only by the political process. Even though coercion is inherent in conditional offers, we should trust offenders to choose between complying with the conditions and staying in prison longer because they generally benefit from that choice. And, in light of the president's role under the pardon clause in making judgments about optimal punishment, presidents can alter the sentencing framework set by Congress. Oversight by Congress, the press, and subsequent presidents tempers presidential overreaching. This Article argues, however, that judges can play a critical role in helping check abuse of the conditional pardon power in two contexts. First, judges should negate a presidential condition in the rare case when the condition shocks society's conscience, such as requiring a prisoner to donate a kidney. Second, offenders should also be entitled to challenge any condition that violates constitutional restraints on the president's authority such as a First Amendment ban on providing support for particular religious expression. In short, although there should be no review of the process by which presidents reach the decision to pardon, the reasons for the decision, or the appropriateness of the condition selected, limited review of conditions that shock the conscience or violate constitutional restraints on presidential authority is warranted.