Background:
 
The unexpected result of an extramarital affair between Spoiled Rich and Flam, Oleander was trouble from the start. His parents’ “courtship” was quick and dirty, taking place over a single weekend that began at Spoiled’s husband Filthy Rich’s annual company Hearth’s Warming party. It ended on the following Sunday afternoon with Flam waking up next to a mare nearly double his age, the wife of their biggest client. Luckily she was still asleep, but just as Flam was slipping out the door he came face to face with Filthy Rich returning home, disheveled in a way that suggested his night was not too different from his wife’s. Flam bolted out the door without a word and was relieved when Rich made no effort to run after him.  
Flim and Flam supplied Filthy Rich with a number of “efficiently sourced” products which they sold at half the price of their competitors. The low prices came with slightly lower quality and were produced under questionable circumstances. They dismissed accusations that they used sweatshop like “hive factories” in the Changeling lands to make their goods, claiming their factories outside of Equestria were entirely automated. Flim even believed that was true for a while, thinking that his brother was saving money using the machines he invented. He had always been the more idealistic, inventive, and naive brother, Flam was more cynical. Throughout their lives, Flam always felt like he had to shield his foolish brother from harsher realities, and Flim had gotten more aware of this as he had gotten older. Despite this, he still usually preferred to believe a comfortable lie than an uncomfortable truth.  
When Oleander was born it was obvious he couldn’t be Filthy Rich’s son, something Rich had suspected from the start. When he and his wife had wanted to have kids it had been a struggle for them, so the possibility of them conceiving by accident had been slim even when they had been young and could stand to be around each other for more than a few minutes. Spoiled hadn’t even realized she was pregnant until almost halfway through, despite numerous doctor visits where she would assure the doctors there was no way she could be pregnant and demand they come up with another explanation. Both parents were in their 40s when Oleander was born and they were less patient with him than they had been with their first daughter Diamond Tiara.  
While Spoiled showed her son the occasional kindness, Filthy Rich was openly resentful at best and viciously cruel at worst. He either acted like Oleander didn’t exist or existed as an object for him to relieve his frustrations on. Once he was old enough to think Oleander realized he preferred the former over the latter. After that, he avoided his “father” at all costs and Filthy Rich had no problems with that. He despised the foal, he had always been a mistake and their family’s deepest disgrace. Despite their first, and only true daughter, who had been born small and weak, Oleander had been born disgustingly healthy and strong. There had never been a moment where Rich had worried he wouldn’t survive infancy, even a fall from the top of the stairs barely seemed to phase the kid.  
Despite this, family life was relatively tolerable for Oleander during the first few years of his life. This was almost entirely due to the presence of his sister, Diamond Tiara. She loved him dearly, more than their parents had ever loved her. She took the brunt of what their parents dished out during that time, giving Oleander the love and affection their parents didn’t. Unfortunately, she was still a teenager, so her parenting wasn’t perfect. One major area both his sister and parents neglected was the fact that, unlike the rest of his family, Oleander was a unicorn. Unicorns need to be taught to control their magic from a young age, beginning almost at infancy when their magic is weakest. If a unicorn isn’t taught proper magic regulation they can become uncontrollable, especially when puberty hits and their magic gets exponentially more powerful.¹  
Whether things got worse or just never got better, eventually, Diamond Tiara couldn’t stand living with her family. When Oleander was 10, she left. The night she left the house she only said goodbye to Oleander, promising to write him letters and eventually come back for him when she could. He promised he would be strong and brave for her, and she never came back. He never got any letters or cards or presents for his birthday from her again, and the resulting heartbreak eventually turned into deep resentment and anger.  
Diamond Tiara did write Oleander, but none of the letters ever reached him. When he asked his mother if he had gotten anything in the mail she just scoffed, and he knew better than to ask his dad for anything unless he had no other choice. Spoiled Rich used Diamond Tiara as a weapon against Oleander, interchangeably blaming him for her leaving and mocking his belief that she had ever really cared about him. Eventually, Oleander began to believe his mother and blamed himself for her leaving, and even his fond memories of her soured over time. It didn’t help that Diamond Tiara’s behavior was infamous among the teachers of Ponyville, even some students heard stories about her from parents who had once been a victim of her bullying. Hearing these stories and feeling the influence of them on how other ponies saw and treated him made him even more resentful.  
After Diamond Tiara left, things in the Rich household continued to deteriorate. Oleander’s father got more violent more often, and his mother started sending him to bed right as he came home from school so she wouldn’t have to worry about him. When he complained, telling her she wasn’t tired, at first, she got angry. Then, oddly enough, she asked Oleander if he wanted a warm glass of chocolate milk to help him sleep. He was confused but knew better than to refuse a treat, and it did help him sleep. He barely remembered anything past the first few sips, and the next thing he knew his alarm was going off and it was the next morning. He got up for school and when he got home his mother again offered him a glass of warm chocolate milk, and this pattern went on for several years until Oleander got to secondary school and caught on to what his mother was doing. By then he had developed a dependence on his daily glass of “chocolate milk”, but having an awareness of the game allowed him to cheat it slightly. His go-to move was taking the glass upstairs to his room and pouring it into a bottle, leaving the empty glass on his bedside table. When he heard the sound of his mother leaving out the front door he would do the same, going out to cause whatever trouble he wanted while sipping on his spiked chocolate milk. The bottle usually lasted him until the next day, when his mother would give him another glass of milk he’d use to refill the bottle.  
¹ I’ll write more about magic logistical stuff later but for now: just know magic development in this universe follows a similar pattern to human brain development in terms of being super weak and unrefined at first and then getting better through learning, experience, and physical development
 
 
Personality:
 
Flamboyant, with a devil-may-care attitude that masks his own self-hatred. He has a fiery temper and a cruel streak. He trusts very few and is extremely manipulative, but more than anything, he is a deeply, deeply angry pony. Although to many he seems cold, calculating, self-preserving, and sociopathic, this is all a facade. Oleander is not a sociopath by any means, his emotional intelligence has always been high. He’s completely aware of how bad cruelty feels, how much pain it causes the victim in question. When he intentionally does something cruel, which he does pretty often, it’s the awareness of cause and effect that motivates him. He’s often impulsive, driven by strong primal emotions and a need to even an imaginary score against everyone.  
His special talent is botany, particularly botany that involves plants with poisonous and/or medicinal qualities. It’s not very well refined, most of his ability is purely magical and intuitive. He can’t tell you the name of a specific mushroom but he can tell you what to expect after eating it.  
Oleander’s powers are heavily influenced by his emotional state due to his poor understanding and control over them. This can result in unfortunate situations like him accidentally causing plants around him to wither and die if he’s feeling depressed or causing destructive plant growth from a burst of happiness. This is largely due to neglect he faced as a young foal. Every pony race has unique needs, and for unicorns that manifests in the need for foals to be taught magical self-awareness and control. There are many different games and activities common in unicorn communities that focus on helping young foals understand and control their magic through play. Whether or not Oleander’s parents knew about this special need is hard to say, but they were either ignorant of or willfully ignored this need because Oleander never learned any real magic regulation skills. This lead to even more trouble at home when magical “outbursts” caused regular destruction and irritation…which unfortunately was then taken out on him both physically and emotionally. It also made him a real pain in the classroom, which soured his teachers’ attitudes towards him.
 

 
oleander……TWO!!!!!!! oleander 2.0. the next next generation  
I’ve revised this guy a lot he’s changed a lot, so I wanted to update his bio. It’s not a complete overhaul of his character but it’s close!
 
also i gave flim and flam a last name and it’ll have relevance later. fun fact! flim & flam’s mom is also trixie’s mom. different fathers though. the family tree about to be complicated (i’m working on that too) (lots of stuff i’m doing rn)