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Given the federal courts’ reluctance to provide clarity on the degree to which the First Amendment safeguards the free speech and association rights of immigrants, the immigration policy agenda of the President now appears to determine whether noncitizens engaging in speech, activism, and advocacy are protected from retaliation by federal immigration authorities. This Essay examines two themes: first, the discretion exercised by the Executive Branch in the immigration context; and second, the courts’ ambivalence when it comes to enforcing immigrants’ rights to be free from retaliation. To do so, this Essay explores the Supreme Court’s influential 1999 decision in Reno v. American- Arab Anti-Discrimination Committee, which held that statutory restrictions on judicial review prevent noncitizens from bringing First Amendment-based selective deportation claims as a defense to deportation. In particular, it draws attention to the Court’s implicit suggestion that foreclosing judicial review of such claims was necessary to preserve the legitimacy of positive exercises of prosecutorial discretion to the benefit of immigrants. The Essay then turns to the relationship between executive discretion in the immigration context and the possibility of robust, judicially enforceable First Amendment protections for immigrants, especially individuals facing immigration enforcement action. It highlights how a different dimension of executive discretion—the operation of low- and mid-level discretion in the deportation state—provides agency officials with extensive opportunities to retaliate against noncitizens for their political speech and activity. The Essay concludes with the suggestion that judicially enforceable First Amendment constraints on this low- and midlevel discretion are both possible and necessary, while expressing concern over the Supreme Court’s endorsement of broader restrictions on noncitizens’ access to the federal courts.