Contemporary scholars, extending back to Hans Windisch's 1924 commentary on 2 Corinthians, have pointed to parallels between Paul's language of ‘boasting’ in 2 Cor 11–12 and Plutarch's treatise de laude ipsius. But would an ancient reader have made this connection between Paul's letters and discussions about self-praise (περιαυτολογια) in ancient rhetorical and philosophical writings? This paper demonstrates that John Chrysostom, the rhetorically trained Antiochene, did just that, particular in his fifth oration de laudibus sancti Pauli, where he defends Paul's ‘speech about himself’ on precisely the grounds Plutarch allowed for inoffensive boasting in his famous treatise.