We report the discovery of an approach to functionalize secondary alkylamines using 2‐halobenzoic acids as aryl transfer reagents. These reagents promote an unusually mild carboxylate‐assisted oxidative addition to alkylamine‐derived palladacycles. In the presence of Ag(I) salts, a decarboxylative C(sp3)–C(sp2) bond reductive elimination leads to γ‐aryl secondary alkylamines and renders the carboxylate motif a traceless directing group. Stoichiometric mechanistic studies were effectively translated to a Pd‐catalyzed γ‐C(sp3)–H arylation process for secondary alkylamines.