What are some of the ways you think gatsby failed to accomplish his dreams?

It's been a while. I'm assuming the girl is Lucy

Gatsby by had always wanted wealth and had possibly resorted to underhand means to achieve it.
Yet he would never be able to achieve old money, the type of wealth and fame accumulated over the years, and the same type that was cheated from him by the dead captain's relatives.
Gatsby also failed to get together with Lucy, the love of his life. He bought a mansion right across from her's and held parties hoping that Lucy might attend one of them. Yet he could never get together with her. Lucy still chose to stay with Tom, and Gatsby was fatally shot by Wilson before he could try again.

So. Old money. Love.