I believe the key to this passage is the word "night". Night, throughout scripture, is associated with sin and deception. We can think of Issac being deceived in the darkness (poor eyesight) by his son Jacob whose very name means - the deceiver. We can see also how Jacob himself was deceived under the cover of darkness by his father-in-law Laban switching Leah for Rachel as Jacob's wife. Even more apparent is the case of Judas Iscariot who after reclining at table with the Lord the night before He died went out away from Jesus and the other disciples and scripture tells us, "it was night."
So, in today's Gospel we are not to understand this as Jesus coming as a thief but rather He will come at a time that we do not know and that time, God forbid, may be a time of "night" or sin for us. Woe to us if He appears as a thief in the night for that can only mean we are living in darkness and sin.
Saint Paul confirms this when he says, "But you, brothers, are not in darkness, for that day to overtake you like a thief. For all of you are children of the light and children of the day. We are not of the night or of darkness. Therefore, let us not sleep as the rest do, but let us stay alert and sober. Those who sleep go to sleep at night, and those who are drunk get drunk at night. But since we are of the day, let us be sober, putting on the breastplate of faith and love and the helmet that is hope for salvation. For God did not destine us for wrath, but to gain salvation through our Lord Jesus Christ, who died for us, so that whether we are awake or asleep we may live together with him." 1 Thessalonians 5:4-10
Jesus Himself also confirms this in Revelation 3:3. He says, "If you will not awake" meaning if you do not arise from darkness and sin and leave the "night of sin" behind, "I will come like a thief and you will not know what hour I will come upon you." Which implies that if we are faithful, if we are repentant, if we cling to Him and His Church, His coming will come as no surprise. Let us prepare for this coming during this time of Advent.
Amen. Come Lord Jesus! (Revelation 22:20)
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