Did he just say "blessed"? Wait... What?

Luke 6:20-26 NASB

And turning His gaze toward His disciples, He  began  to say, "Blessed are you who are poor, for yours is the kingdom of God.  "Blessed are you who hunger now, for you shall be satisfied. Blessed are you who weep now, for you shall laugh.  "Blessed are you when men hate you, and ostracize you, and insult you, and scorn your name as evil, for the sake of the Son of Man.  "Be glad in that day and leap for joy, for behold, your reward is great in heaven. For in the same way their fathers used to treat the prophets.  "But woe to you who are rich, for you are receiving your comfort in full.  "Woe to you who are well-fed now, for you shall be hungry. Woe to you who laugh now, for you shall mourn and weep.  "Woe to you when all men speak well of you, for their fathers used to treat the false prophets in the same way.

My thoughts -

That Jesus fellow is an odd, odd bird. Maybe I didn't hear correctly. You know, I do have trouble hearing sometimes. But I swear he just said that the poor are blessed. Not only that but woe to the rich?

Now, far be it for me to argue with such an esteemed teacher but how can this be? Aren't the rich blessed? Can't we tell that God favors them by how God has blessed them? When we suffer isn't because God is punishing us?

If we are hungry, or poor, or scorned; if we suffer isn't it because we have done something wrong? Isn't that God's way of calling attention to our sin and demanding that we repent? Don't we suffer because we deserve it?

And we know the rich deserve how God has blessed them. I mean, look at our history. Some of our greatest kings were wealthy beyond our wildest imaginations. Look at Solomon. Look at David. God blessed them beyond measure. Didn't they deserve it? Don't the rich deserve to be blessed? Isn't that how God has ordered things? Be righteous and be blessed. Be a sinner and be punished. If you suffer you deserve it.

Yes, I suppose Job didn't really deserve his afflictions. But that's different. Job was sort of the exception that proves the rule, right? And I suppose there have been more than a few righteous widows. They seem to always be helping prophets out in scripture. But we don't know a lot about them. And maybe they had been punished by God for some previous life of sin we don't have access to.

Where is Jesus coming from with this whole "blessed are the poor thing", anyway? Doesn't he know anything? It just doesn't make any sense. It's so confusing. I don't understand.

But what if he's right? What does that mean for us? If the poor and the hungry and the suffering and the loathed and the shunned and the powerless and the oppressed are blessed are blessed by God what does that mean for me? Should I care for them? Should I have compassion? Should I do anything differently?

And when Jesus says "woe", what does that mean? Do I even want to know?