The call of Judas highlights the great mystery of grace and its complex interaction with human free will. Judas was called to be an apostle and not a traitor—despite some claims to the contrary. But instead of ensuring a deeper union with Christ, it resulted in his treacherous betrayal. Might he perhaps have been spared this great sin had he remained a simple disciple and not a more privileged apostle? We will never know. What we do know is that persevering in our fidelity to Christ can never be taken for granted and falling away from Christ is always a frightening possibility. Our own privileged monastic call is thus not only an occasion for deep gratitude, but also grounds for special vigilance lest we follow Judas’ tragic path to destruction.