Seeing the world through a theological lens...
One of the lawyers answered him, “Teacher, when you say these things, you insult us too.” And he said, “Woe also to you lawyers! For you load people with burdens hard to bear, and you yourselves do not lift a finger to ease them. Woe to you! For you build the tombs of the prophets whom your ancestors killed. So you are witnesses and approve of the deeds of your ancestors; for they killed them, and you build their tombs. Therefore also the Wisdom of God said, ‘I will send them prophets and apostles, some of whom they will kill and persecute,’ so that this generation may be charged with the blood of all the prophets shed since the foundation of the world, from the blood of Abel to the blood of Zechariah, who perished between the altar and the sanctuary. Yes, I tell you, it will be charged against this generation. Woe to you lawyers! For you have taken away the key of knowledge; you did not enter yourselves, and you hindered those who were entering.” When he went outside, the scribes and the Pharisees began to be very hostile toward him and to cross-examine him about many things, lying in wait for him, to catch him in something he might say.
The divide between Jesus and the Pharisees was growing wider; there was no getting around it. Jesus may have started out being only marginally annoying to the religious leaders with his healing on the Sabbath, and hanging out with "sinners." Even his story telling they could probably have tolerated, though his parabolic style left them scratching their heads more often than not.
But this- this, "woe to you" language- this was over the top. How dare he criticize? Anyone who knows anything about the law, religious or otherwise, knows that laws were created for a reason! We need to have protocol. We need dogma and ritual. The people need to know what to do and how and when to do it- the why is not important. They need to know right from wrong, and isn't it the responsibility of the pharisees and the lawyers and the scribes to instruct? To teach people what's best for them? What will keep them in line with God's teachings and give them a good slap when they fall out of line?
I don't believe Jesus was negating the necessity of teaching. The people (we) do need to know what's right and wrong, and we should be able to turn to our religious leaders to help us on our journey. That doesn't sound like anything to which Jesus would object.
The issue for Jesus Is that the law had become a burden to the people instead of a life bringing, love enhancing guide. What started out as "take the sabbath as a day of rest" (which was a blessing and a good thing for a people who have a hard time slowing down) became, "if you do any work on the Sabbath, you will be punished." Can you see the difference there? One is life affirming and renewing. One is oppressive and taxing.
There were 613 laws like this that religious people needed to keep, and consequences for breaking each. That is a lot of pressure, or what Jesus calls, "burden." And worse, they had "taken away the key of knowledge" (v.52) meaning, a deeper understanding of God's love for them, by watering down the law into a black and white list of dos and don'ts.
Before we judge and want to get all crazy angry at the religious leaders, know that they had inherited and grew up in that system; they were taught, and believed, that what they were doing, and how they were interpreting the law was correct, and Godly. They were as much blinded by the system as much as we are often blinded by the systems of oppression and greed that exist in our word today. It's why Jesus calls them at one point, "Blind guides!"
When someone points this out to us, both the brokenness of our systems, and the part we play in perpetuating them, and when that someone says, "woe to you," it can feel both insulting and demeaning.
A quick aside about "woe." It simply means "watch out", or "here's a warning because you're doing the wrong thing." In it's most basic form, it's like a mother cautioning a child to get their homework done, not because of punishment, but that the child will suffer the consequences down the line.
In this case, Jesus warns the leaders that they, by framing God as a punitive being, they are bringing hardship, destruction, and calamity, now and down the line.
The divide with the religious leaders and the people who follow them, also swept up In the system, will lead to Jesus's death. For us, with 2000+ years of hindsight in our pocket, we can see how wrong the Pharisees were. Yet, it's worth a good long look into our own lives. How are the laws we follow, sometimes blindly, perpetuating systems of oppression and greed? Are we living out the letter of the law, or the generous love of God? Is there a balance? And... should there be?
No easy answers today- It's Lent after all.
Much love and peace to you,