Expositor's Bible Commentary Commentary Philemon 1:8

"Wherefore, though I have all boldness in Christ to enjoin thee that which is befitting," — Philemon 1:8 (ASV)

Paul first reminds Philemon of his apostolic authority. “Bold” (GK 4244) has the idea of “freedom” or “boldness.” Here it implies “right” or “authority”— hence, “I could be bold and order you.” The suggestion of authority was probably enough, coupled as it was with the appeals to love, old age, and imprisonment in v.9.