Oliver was one lucky son of a bitch, and he knew it too.

Being born into one of the wealthiest family in America, he has lived a life where anything he wanted could be his by the snap of his fingers. Wanted a new car? He got it. Wanted a new motorcycle? Sure, only the best money can buy. Didn't do his school work for the entire year? It doesn't matter seeing as his parents always covered for him, throwing their money at whoever could help their child pass the grade.

His parents knew that perhaps they should have been less lenient towards their child, especially after the years that had gone by, because Oliver was becoming more and more of a trust fund baby each year. Always relying on their money to get him out of trouble or cause the trouble. Though how could they be the parents they know they should be when they were never home. Always away in business with only maids to take care of him, and soon enough his younger sibling, Thea. Not even five years young and she already had a maid of her own.

Oliver resented his parents as soon as he became a teenager. He had joined every sports team his private school had to offer, in hopes his parents would be proud of him, and they were even though they never say anything about it. Not once had they attended Oliver's sports game to cheer him on, and perhaps that when he just stopped trying. Oliver finally realized that no matter what he did his parents would never notice him. Never care.

So he began acting out.

It started with little things like getting detentions. Next came the fights and stealing his parents' car (though he thinks it's more borrowing than stealing). Then came the DUI's and not to mention his latest crime, peeing on a cop car.

His parents had warned him about his crime sprees of course. Robert Queen specifically told his son that if he didn't get his act together that he would be cut off. Oliver knew his dad would never actually do that to him seeing as he was his only son. Though not wanting to test his patience, Oliver decided to lay low. Or as low as you can while being Oliver Queen.

He and his partner in crime, Tommy Merlyn (another trust fund baby) decided to travel all around the world. Of course that was after being kicked out of three Ivy League schools.

After being away for almost two years, the two were finally back in Starling City. Not only are they back, but have decided to open up a night club. Using their parents' money of course. Robert wasn't pleased to hear about his eldest son opening up a night club. He wanted to start preparing him to take over the family company but Oliver had made it clear to his father that he didn't want to be CEO. They fought that night. Words were thrown carelessly and threats were made.

"God Oliver! You're almost twenty five years old! Don't you think it's time to grow up?"

He scoffed, taking a step closer to his father. "Oh I've grown, Dad! I want to have this business but of course seeing as it's not what great Robert Queen has planned for his son that automatically translate to me not wanting to grow up! When are you going to understand that I don't want to be like you!? I don't want to be you, Dad."

"Fine Oliver. You don't want to be like me? Then don't. You can fend for yourself. I'm done being your personal bank!"

Oliver paled at his words. "—Wait Dad! That's not fair! I'm your son, you can't do this to me!"

Robert immediately cut him off saying, "I'm done Oliver. I'm done. You are such a disappointment."

With one lasting look at his son, he stepped out of his office, leaving Oliver standing in the middle of the room, flabbergasted at what just happened.