In my opinion Jay Gatsby didn't achieve his dreams.
You would think that he had made all his dreams come true. Rising from a farm boy to an overnight man of means. Jay Gatsby, the man with the big house, ridiculous amounts of money, and flashy parties, really wasn't interested in any of it. He's invested his dreams, goals, practically framing his life around the notion that maybe some day, he and Daisy would be together.
"He hadn't once ceased looking at Daisy, and I think he revalued everything in his house according to the measure of response it drew from her well-loved eyes. Sometimes, too, he stared around at his possessions in a dazed way, as though in her actual and astounding presence none of it was any longer real. Once he nearly toppled down a flight of stairs."
No, he didn't obtain his true objective. To have Daisy, and sadly we see at the end of the story, that the only true closeness he could feel with is love, is the green light separating the two.
"he stretched out his arms toward the dark water in a curious way, and, far as I was from him, I could have sworn he was trembling. Involuntarily I glanced seaward—and distinguished nothing except a single green light, minute and far away, that might have been the end of a dock. When I looked once more for Gatsby he had vanished, and I was alone again in the unquiet darkness."
In my opinion, Jay Gatsby in F. Scott Fitzgerald's novel The Great Gatsby did not accomplish his dreams.
Gatsby's dream was to be married to Daisy and, more expansively, to be worthy of Daisy's love. To achieve that end, he set about making his fortune. He did achieve his fortune, but, as you can see from reading the novel, the parties and the money did not make him happy.
He met Daisy five years earlier at her home in Kentucky. He was about to go off to war as an officer in the army. Daisy's family was wealthy, and her mother pressured her to find a good marriage. Daisy was forbidden to go to New York to see Gatsby as he went off to war.
It was Gatsby's own insecurities and humble beginnings that made him feel he was not worthy of her. After the war ended, he did everything he could to become worthy of her. In the meantime, Daisy met and married Tom. Tom was a very wealthy man when he married Daisy. He came from "old money," which meant his success was generational. His family was established and well-known for their success. Gatsby, after he earned his fortune, was what was called "new money," and the old money types scorned the newly rich as beneath them.
Gatsby built a grand castle of a house across the bay from Daisy's house. He throws parties every weekend and asks around to see if anyone knows Daisy. Finally, he finds out that Jordan Baker knows her and that Nick is her cousin. He asks Nick to invite Daisy to tea so he can be reunited with her. Prior to their meeting, he invents a story about his past to tell Nick Carraway. This invention is for the purpose of being considered worthy of Daisy. He understands how "new money" people are perceived, so he invents a story to show that he is not one of them.
"I am the son of some wealthy people in the Middle West all dead now. I was brought up in America but educated at Oxford, because all my ancestors have been educated there for many years. It is a family tradition." He looked at me sideways and I knew why Jordan Baker had believed he was lying. He hurried the phrase "educated at Oxford," or swallowed it, or choked on it, as though it had bothered him before.
After Gatsby's relationship with Daisy begins to blossom again, he reveals his dream to Nick. He has amassed all of his wealth, bought a house overlooking Daisy's, thrown parties every weekend, and invented the story of his past all for this purpose. The dream is found in the quote below:
He wanted nothing less of Daisy than that she should go to Tom and say: "I never loved you." After she had obliterated four years with that sentence they could decide upon the more practical measures to be taken. One of them was that, after she was free, they were to go back to Louisville and be married from her house just as if it were five years ago.
Gatsby wants to simply erase the five years in which he was separated from Daisy. Nick tells him that the past cannot be repeated. Gatsby replies "Can't repeat the past? Why of course you can." The problem is that Daisy does love Gatsby, but she cannot deny that she loved Tom, too. She had a child with Tom, and she does have some happy memories of him. Daisy is willing to let Tom go, but she is not willing to say what Gatsby wants her to say—she is not willing to erase the five years.
Following Daisy's denial of Gatsby's dream, the accident in which Myrtle is killed happens, and Daisy and Tom cling together, leaving Gatsby shut out of her life once again. Nick says they were careless people, Daisy and Tom. Gatsby is murdered in the end by Myrtle's husband, and his dream is never realized.