So I started with just the text and Gordon Fee’s commentary on 2 Thess. And I soon worked with just the text as I found Fee too unwilling to consider the possibility that these events had already happened. He prefers a metaphorical interpretation — an interpretation that doesn’t really serve Paul’s purposes in writing 2 Thessalonians.
If we assume that Paul is right (and that 2 Thess isn’t some so-called Deutero-Pauline text but truly honest-to-God inspired scripture), then there has to be an answer. Follow the evidence.
When I finished my own, independent study, I went through over a dozen commentaries and found that nearly all offer no theory at all. Some suggest that Paul is offering a metaphor for any rebellious leader (seriously?). Some assume the Left Behind theory. Some list obviously absurd interpretations (Hitler, Stalin, the Pope) to demonstrate the impossibility of knowing what is meant. Some conflate this text with the mark of the antichrist, the beast, 666, and all that — which is unwarranted. He’s not called a beast or given a number by Paul. We can’t just assume to be true what we wish to be true.
Regarding Luke 17:23, Evans notes,
In Luke’s church the tragic war with Rome (A.D. 66–70) may very possibly be in mind. Many Jews followed a would-be messiah named Simon bar Giora (as well as other leaders). Through his leadership it was hoped that Rome would be defeated and the kingdom of God inaugurated. These hopes and aspirations proved to be unfounded, and the city of Jerusalem, along with its temple, was destroyed.
Craig A. Evans, Luke, Understanding the Bible Commentary Series, (Grand Rapids, MI: Baker Books, 1990), 264.
Regarding Matt 24:26,
Such “false Messiahs and false prophets” active during the siege might include Simon bar-Giora (Josephus, War 4.503–544 etc.) who was regarded as a “king” (510) and eventually paraded and executed in the Roman triumph as “the enemy’s general” (War 7.153–154), and also “many” false prophets noted anonymously in War 6.285–288; that last passage goes on to relate (6.289–300) a series of signs and wonders occurring in the period before the city was destroyed which some took (wrongly) to be omens of deliverance.
R. T. France, The Gospel of Matthew, The New International Commentary on the New Testament, (Grand Rapids, MI: Wm. B. Eerdmans Publication Co., 2007).
Menahem and Simon bar-Giora, two of the would-be messiahs of the war against Rome (A.D. 66–70), presented themselves in public in the Temple before being killed, one by rival Jews, the other by the Romans during Titus’s triumph.
N. T. Wright, The Challenge of Jesus: Rediscovering Who Jesus Was and Is, (Downers Grove, IL: InterVarsity Press, 1999), 63.
Thus, the historians agree that Simon bar Giora made fairly prominent messianic claims, was the primary leader of the rebellion against Rome (the Romans made a point to execute him in Rome), and a brutal, cruel leader. It’s easy to imagine Paul, with apostolic foresight, speaking very harshly of someone claiming to be the Messiah (and so denying Jesus) and leading God’s people into a futile, suicidal, brutal war with the Romans against the announced will of God. The language of 2 Thessalonians has the tone appropriate to such a person.
Some argue that Paul seems to be arguing that the Rebel will appear just before the Second Coming, but this same claim could be made as to Jesus’ words in Matt 24 — and yet they aren’t right. I think we’re unconsciously reading our own traditions — the Anti-Christ theories — into the text.
For Paul’s original readers, if he’d covered Jesus’ speech over Jerusalem recorded in Matthew 24 in his teaching with the Thessalonians — and why not? — then he’d quite naturally say that, obviously, since Jerusalem is not yet fallen, the Second Coming hasn’t yet happened. Indeed, the only thing we know for sure regarding the timing of the Second Coming from the scriptures is that it would occur after Jerusalem is destroyed!
With one exception , no one that I’ve found associates Simon bar Giora with the Man of Lawlessness because most don’t see Paul as talking about the destruction of Jerusalem — and yet based on the Gospels, the destruction of Jerusalem is the ONLY thing Paul could be talking about because it’s the ONLY event that Jesus assures his followers will precede the Second Coming. And it seems unlikely that in the same series of letters in which Paul says the Second Coming will come “as a thief in the night” that he’d be adding to the events that make the timing knowable.
Paul himself says he’s repeating lessons already taught. And it makes perfect sense that the lesson taught in Matt 24 would have been a part of Paul’s teaching. After all, in 15 years, the Temple would be destroyed and Jerusalem would fall. His students needed to know how to fit these cosmic events into their understanding of Christianity.
It’s not complicated — just obscure because few Christians study the history of the fall of Jerusalem and see it as being as significant as it was to Jesus and Paul.
 See Pilgrimer’s comment at August 14, 2013, 6:34 PM.