Dare We Challenge the Wise?

I've listened to an NT Wright sermon I found on veritas. He was speaking to a group of students at Yale in 1995. Like any NT Wright work, I've listened to it 4 times already, and still don't totally understand what he's saying. But here's my initial thoughts so far:

From his insights about the era, he gives two great responses about the resurrection:

1. Judaism typically reveres the place of burial for a hero. We read nothing of the apostles or other followers returning to the tomb to pay homage to Jesus. Not only do His most devout followers neglect the tomb, but even the casually interested don't take a pilgrimage to the tomb. Why not? There really is no explanation unless the tomb is empty.
2. Messiahship was typically passed on through the family. When people would rally around someone as their messiah, and he was killed by the government, people would annoint a close relative as successor. James clearly plays a prominent role in the early church, yet no one proclaims him as messiah. Why not? The only explanation is that the church considered the crucified Jesus as their Messiah. Perplexing decision, unless the church knew Jesus to be resurrected.

...but what concerned me:

1. "Jesus believed He was" This phrase is uttered a lot. I know I'm going to drop the ball describing this, but in it's context, it seems to distinguish between reality and Jesus' imagination. Almost as if Wright were saying, "Whether true or not, it appears that Jesus believed it to be true." That just makes me uncomfortable.
2. Jesus compared to false messiahs. Sure, several different men claimed to be the messiah around the time of Jesus. Many even had a pretty solid following. The agenda of these "would-be-messiahs" helps us see what agenda resonated with people, and even the way a person gathered a following, but it doesn't mean Jesus followed the same format. Jesus' agenda was totally different and everything He said doesn't need to match the actions of "pseudo-messiahs."

...and the big issue that consistently troubling about NT:

In an effort to reconstruct, he often deconstructs too much. Much of Wright's work is very valuable to the understanding of first century Judaism. His research allows us to understand some things in light of the original context rather than reading the 21st century backwards into the Biblical texts. However, he seems to get carried away at times. In effort to explain his understanding of a passage in Luke, he readily throws out information from church fathers in the second century. He doesn't even seem to blush at the notion that he knows better than those only 50 years removed from the incident.

Contrast this with an interview on Talk the Walk with Todd Friel. He interviews Michael Medved who explains why Jews accept the rabbinic teachings. They believe they are following oral teaching they have received from their instructor. Medved explained that a rabbi from 1,000 years ago is "one thousand years closer to Sinai," therefore he must consider his credibility.

Wright seems to be a nice enough guy, but this kind of mindset seems to escape him. His perspective on Paul and justification suggests he believes the reformers got it totally wrong (as well as other church fathers: see Augustine). He questions the authenticity of some books of the Bible (or at least does not defend the Cannon). He's even willing to redefine the words of Jesus, or how his followers interpreted it.

I would never want to wrestle words with NT Wright, he is far too intelligent. And I appreciate his desire to question things. But I worry that sometimes the "destruct-reconstruct" method requires a bit of arrogance to assume we can know more than people of past generations. Are we really wise if we think we are more wise than others?