The startling reality of Paul’s apocalyptic discourse in 2 Thessalonians 2:1–12 is that its purpose is comfort (vv 1-2). While much of scholarship attempts to identify the man of lawlessness, the question that this passage begs is how this apocalyptic teaching is comforting. I propose that Paul refers to the prophetic image of oppressive, non-Israelite rulers in 2 Thess 2:4, in order to reveal the man of lawlessness as the final agent of Satan against the people of God, thus counterintuitively comforting the Thessalonian church with sure victory. To show how Paul’s allusion to this OT image is comforting I will analyze in this paper the characters that make up this image. Those characters are the King of Babylon (Isaiah 14), the Prince of Tyre (Ezekiel 28), and the Northern King (Daniel 11). Each of these characters have a self-exalted status in the place of the gods, thereby blaspheming Yhwh, resulting in certain defeat. This certain defeat is the implied source of comfort for Paul’s audience in 2 Thessalonians. This study aids in understanding 2 Thess 2:1-12 within Paul’s apocalyptic read of history, the OT, and the second advent of the Lord Jesus.