Could you perhaps flesh out why 'picking up the cross' would be understood as counter-imperial? Could it not equally be understood as resignation, acceptance of Roman power of them.
It seems to me that while this remains within the realms of the possible, given the context of Jesus' teaching and announcement, it remains unlikely. As I hope to demonstrate in the near future, Jesus saw his mission and message as one announcing the return and reign of YHWH over the regathered people of YHWH.
The evidence which we will survey suggests that Jesus' attitude to the Romans was much like that described in Josephus with the speech of Eleazar ben Yair, commander of the defendants of Masada, noted their determination:
Long since, my brave men, we determined neither to serve the Romans nor any other except YHWH, for he alone is humanity's true LORD; and now the time is come which bids us verify that resolution by our actions. (J.W. 7.8.6 §323)
The connection seems clear then: those who incited revolt against the authority of Rome were crucified. Thus, Jesus' use of the image pick up your cross, suggests 'embrace' the revolution. Given Jesus' teachings on being peace-makers, loving enemies, turning the other cheek and the specific command not to antistenai [resist] evil [See discussion in JVG, pg. 291], it seems axiomatic that the revolution he was proposing was not one of military instigation or violence.
So to conclude, Tom Wright is possibly correct in his parody:
Jesus was more like a politician on the campaign trail than a schoolmaster; more like a composer/conductor than a violin teacher; more like a subversive playwrite than an actor. He was a herald, the bringer of an urgent message that could not wait, could not become the stuff of academic debate. He was issuing a public announcment, like someone driving through a town with a loudhailer. he was issuing a public warning, like a man with a red flag heading off an imminent railway disaster. he was issuing a public invitation, like someone setting up a new political party and summoning all and sundry to sign up and help create a new world. [Wright, JVG, pg. 172]
Jesus was setting up a KINGDOM/EMPIRE that was directly opposed to that of the Roman emperor. His was one of authentic peace via a renewed covenant with YHWH through himself. Jesus was the reality of which Caesar was merely the parody. If the earth is YHWH's and everything in it, (Ps 24:1) if the gospel is for all nations [Mk 13:10], then there can be no other KING but YHWH - and that is exactly what Jesus was claiming.
However, this argument must now be substantiated with arguments for the historicity of the key passages we have made mention of. But I think it can be done and it already arouses interest due to the criterion of historical plausibility [Jews regularly had something to say about Roman oppression] and the fact that Rome finally destroyed this alternative vision by doing what they did to all those who proposed a renascence of sovereignty to YHWH or to Messianic claimants. They crucified them and publicly humiliated that vision and agenda. That's what Pseudo-Quintillian, Declamations, 274 notes:
Whenever we crucify the condemned, the most crowded roads are chosen, where the most people can see and be moved by this terror. For penalties relate not so much to retribution as to their exemplary effect.
Does that satisfy the objector?