Winnifred Freight

Personality

Upon first meeting, Winnifred Freight is a well-mannered, well-dressed young man, though a little self-indulgent. You could say he shows the signs of an only child despite a good upbringing. He's always looking out for himself and catering each situation to himself - if not in the immediate moment, then further along the lines. Win's company isn't exactly unpleasant though, as he avoids being rude or too straight-forward, and may try using gentle methods of social and emotional manipulation to pull the strings his way. To some he might even seem generous, kind and fun to be with, but all favors the Minccino offers (including his charming presence) come with a price.
Sometimes the price is that Win just wants to be around a certain person though, was it for social profile or whatever reasons, in which case he may be especially enjoyable to have around. He has a subtle sense of humor, money and isn't too hard to look at, not to mention all of his connections to arrange your life around with. When you've got Win on your side, he'll personally offer his advantages to you and help you. Having experienced a wealthy upbringing he sees anything not-topnotch as a dire need and therefore won't let his friends have a less than luxurious time when they're with him.

At the same time, Win is often childishly emotional in his own head. He would be wondering why people seem so distant and mean, whilst doing his best to profit from each social encounter in a selfish manner. He's not good at expressing his true feelings and likely drowns his emotional needs with monetary gains and by gently poking at other people's emotions. Relationships, love and friendships are generally just a part of a social game for him, and getting too emotionally invested to someone feels like a burdenous obstacle in the way of "real achievements".
However, Winnifred rarely wishes ill to other people. The matter with him is that he just wants better for himself, which usually comes at the expense of other people. He appears to lack the emotional intelligence to see the wrong in his ways.

Business life and social circles get the Minccino excited. He's top-tier at social games and likes to pull up his pedigree for easy merit, alongside with less impressive and often somewhat shady personal achievements. Not being much of a worker himself, Winnifred has cheated people into debt to work for him, as well as a couple of "Grab the Money and Run" start-up companies, and a little bit of insurance fraud, to name a few of his gambles.
When asked, the fault to his failure at building his own companies and the reason his parents don't trust him with theirs, is always somebody else's.

History

Winnifred Freight was born in 1991 as the only child to a highly educated and hardworking couple in Lumiose City. His parents were always busy with their high-profile business jobs, so most of the time Win was raised and taken care of by nannies and less busy relatives. The boy's relationship with his parents has always been distant but respectful and the couple has never left him feeling needing anything, except emotional support.

During his school years Win earned his nicknames, Win-Win, Win, and so on. Despite having a woman's name and a prestigious background, he wasn't viewed as different from the rest of the students. In fact, Winnifred started to notice his social skills and gained quite a popularity among his peers. His school grades weren't bad either, not top-tier but not average. Throughout his basic schooling, Win never earned support from his parents towards his school work, other than a cold remark if he were to fail an exam or cause trouble at the school. Due to this the Minccino found it hard to motivate himself to study but didn't give up on it either. He was always obedient to his teachers and viewed as a generally good student.

Eventually Winnifred moved on to business school where he could use his background to influence people even more. The Minccino chose this path due to his background, both parents being in business left him with little support for other options. He had also learned his influence-boosting moves - such as Charm - by then, and would even use Echoing Voice in a fitting situation to get his way. This dishonest way of dealing with school eventually led to him failing however, as too many promises and projects hopped on top of eachother and the Minccino found himself overwhelmed with work. He still keeps his connections from the school however but keeps a kind of "too-cool-for-school" attitude when faced about his failure. His parents have yet to accept his failure and are still expecting him to re-enter college.

Winnifred isn't exactly good at failing though. Not succeeding at his school led him to a spiral of depression with a side serving of drugs, alcohol and parties. Despite understanding his patheticity, he reached out to his parents at this time of need and only received a cold scolding from his father. His father's cold words worked however and Win dragged himself out of substance use but still keeps a bitter bite of depression in him. Caring for his public image the Minccino rarely shows weaknesses such as this to other people but may be childishly dramatic in his own solitude.
During his college years Winnifred had moved out of his parents' house and lived on his own in a small studio apartment. His parents would pay for his rent during his mental breakdown simply to save their family from embarrassment but as soon as the Minccino was back on his two feet, they again started requesting him to restart school and held onto their money tighter.

These days to keep up with rent and pay for his living, Winnifred mostly relies on his parents' companies but has also done some dirty work in insurance fraud and the stock market. He has tried doing honest work but always finds himself using his charm and influencing skills to swindle out of work. There's always a couple of people who 'owe him' for whatever he's convinced them, as well as wealthy exes who still hold a soft spot for his cries for help. To cut it short, the Minccino lives an easy life at the expense of other people.

Having so much free time in his hands, the Minccino found the Argo Navis an interesting concept to take part in. He wants to continue using his moves as it comes to him naturally, so recent bans and public fear of move-users has caused Winnifred to be more alert about the issue as well. Without Charm and Echoed Voice his way of getting around things would be much harder, therefore he's absolutely against a move ban. He also thinks AN will bring useful contacts alongside with it, therefore proving useful in the long run, if not only something to do.

Moveset

Swift (Star-shaped rays are shot at the opposing Pokémon. This attack never misses.)
Win swipes his arm in an arch to create star-shaped projections of energy, which are shot at the opponent. This move is rarely used.
Swift he learned as a safe skill to protect himself but Win rarely has to result in physical violence to get out of harm's way.
Side-effect: Using Swift repeatedly will cause Win's arm to blister with burnmarks from the energy of the projectiles.

Charm       (The user gazes at the target rather charmingly, making it less wary. This harshly lowers its Attack stat.)
Win locks eyecontact with the opponent, which captivates them and causes their Attack to harshly lower.
Charm was one of the first moves he ever learned, which he has found quite useful when other people have tried using their moves against him.
Side-effect: Having mastered Charm, the side-effects are kept to a minimum. However, the more people Win tries to influence, the more likely he's to suffer a migraine from using the move.

Echoed Voice   (The user attacks the target with an echoing voice. If this move is used every turn, it does greater damage.)
Win's voice is accompanied by an echo that rings in the opponent's ears. The more Win gets to yell, the more damage Echoed Voice does.
Echoed Voice Winnifred learned naturally in a yelling match with one of his past partners. The experience of hurting his loved one through yelling scared Win at first but later on he's learned to use it as another method for protection. He may also sneak the move in when he wants to leave a stronger mark on someone through public speech and other varying  situations.
Side-effect: The more this attack stacks, the bigger toll it takes on Win's throat, risking losing his voice upon too much use.