1. A person who could learn Torah but doesn’t
2. A person who can’t learn Torah but tries anyway
3. A leader who is haughty with the peopleWe can understand why Hashem cries over the first person, he should be learning Torah and isn’t, but why does Hashem cry over the second person? At least he is trying to learn.R’ Schacter explained the Gemara as follows. Every person is unique with his own set of talents and abilities. Our mission in life is to figure out how to best use those talents in the service of Hashem. Some people have talents that can be used in learning while others have talents (art, music, business, people skills, etc.) that can be used to serve Hashem in other ways.
Based on this it is clear that Hashem is crying for the first 2 people for the same reason. They are not using their talents to serve Hashem. Just like the person with the talent to learn should be serving Hashem by learning, and therefore Hashem cries because he isn’t learning. The person who doesn’t have the talent to learn, should be serving Hashem NOT by learning but by using his talents to serve Hashem in other ways. Therefore when he does try to learn Hashem cries because he is not using the talents Hashem gave him.
This Gemara is telling us a very important principle in life that a person needs to understand what his talents are and based on that figure out what his particular mission in life is and we can’t force everyone into the same mission.
IMHO this is the biggest problem in the religious world today on both sides of the spectrum. The real modern world (e.g. schools like Ramaz, Frisch, Yeshiva of Flatbush) causes Hashem to cry for person 1. People with the talent to go into learning are encouraged to do other things instead. How many modern parents encourage their children to sit and learn Torah? The Charedi world on the other hand causes Hashem to cry for person 2. In the Charedi world every boy is supposed to sit and learn no matter what his talents are and if your talents lie in other areas you are in big trouble in the Charedi world.
What we need is to allow people to serve Hashem based on their talents rather then simply pigeon-holing everyone into 1 thing.