Taken from Medulla S. Thomae Aquinatis which arranges various short texts from St. Thomas Aquinas' corpus based on the liturgical year. I will be posting the day's meditation each day and will be bringing it into print once I'm through it.
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Thursday after the First Sunday of Lent
That It Was Fitting That Christ Should Be Crucified with Thieves
Christ was crucified between thieves from one intention on the part of the Jews, and from quite another on the part of God’s ordination.
1. As to the intention of the Jews, Chrysostom remarks (Hom. lxxxvii in Matth.) that they crucified the two thieves, one on either side, that He might be made to share their guilt. But it did not happen so; because mention is never made of them; whereas His cross is honored everywhere. Kings lay aside their crowns to take up the cross: on their purple robes, on their diadems, on their weapons, on the consecrated table, everywhere the cross shines forth.
As to God’s ordinance, Christ was crucified with thieves, because just as Christ became accursed of the cross for us, so for our salvation He was crucified as a guilty one among the guilty.
2. As Pope Leo observes (Serm. iv de Passione): Two thieves were crucified, one on His right hand and one on His left, to set forth by the very appearance of the gibbet that separation of all men which shall be made in His hour of judgment. And Augustine on John 7:36 says: The very cross, if thou mark it well, was a judgment-seat: for the judge being set in the midst, the one who believed was delivered, the other who mocked Him was condemned. Already He has signified what He shall do to the quick and the dead; some He will set on His right, others on His left hand.
3. According to Hilary (Comm. xxxiii in Matth.): Two thieves are set, one upon His right and one upon His left, to show that all mankind is called to the sacrament of His Passion. But because of the cleavage between believers and unbelievers, the multitude is divided into right and left, those on the right being saved by the justification of faith.
4. As Bede says on Mk. 15:27: The thieves crucified with our Lord denote those who, believing in and confessing Christ, either endure the conflict of martyrdom or keep the institutes of stricter observance. But those who do the like for the sake of everlasting glory are denoted by the faith of the thief on the right; while others who do so for the sake of human applause copy the mind and behavior of the one on the left.
Just as Christ was not obliged to die, but willingly submitted to death so as to vanquish death by His power: so neither deserved He to be classed with thieves; but willed to be reputed with the ungodly that He might destroy ungodliness by His power.
Accordingly, Chrysostom says (Hom. lxxxiv in Joan.) that to convert the thief upon the cross, and lead him into paradise, was no less a wonder than to shake the rocks.
(Selections from ST.III.Q46.A11)