How did Christ triumph over principalities and powers?
Christ triumphed by His work of the cross: He blotted out the handwriting of ordinances that was against us and contrary to us, took it out of the way, and nailed it to His cross. Having spoiled principalities and powers, He made an open show of them, triumphing over them in it.
Les explains from Colossians 2 that the triumph over principalities and powers took place in Christ's work of the cross. The handwriting of ordinances that was against us and contrary to us was blotted out, taken out of the way, and nailed to His cross. Because the law is satisfied, believers are no longer under it, so no one should judge them in meat, drink, holy day, new moon, or sabbath days. Those things flash back to Judaism and the Law, which are now behind us and nailed to His cross, being only a shadow. In that same finished work, He spoiled principalities and powers, made an open show of them, and triumphed over them in it.
And having spoiled principalities and powers, he made a shew of them openly, triumphing over them in it.