Winston is a half-blood. His dad went to the Air Force Academy, upon graduating he was stationed to the RAF base in Croughton where he met Winston's mother who was working as a ministry employee. They fell in love, then the unthinkable happened, Winston's dad who name was Leonard was called home. The couple didn't want to split up, so Winston's mom (Katherine) packed her bags and moved home with her new fiance. Leonard had proposed after she said she would be going with him. The couple was happily married for 2 years when they were blessed with Winston. 3 years later later his sister Kathy was born.
Growing up Winston was very close to his dad. He loved to do everything his dad did. They would go camping together, his dad was Winston's cub scout den leader. Winston was hit the hardest when his Dad was called away to Iraq. His became very depressed and withdrawn, his friends tried to coax him out of his shell, eventually it worked. That's when the news came, Leonard Wolf had been killed in the line of duty. That was when Winston’s first sign of magic showed, in a display of rage and sadness he destroyed the paper that told them of the news.
Winston drew himself into his shell again, this time friends couldn't coax him out of it. He stayed like this for 2 years, when he realized that his dad would want him to be remembered, but also to move on. He slowly came out to find that all his friends had abandoned him. He was alone. Slowly his friends came back to him, but the time alone had marked him. Winston was terrified that he would one day be left alone once more. His Hogwarts letter came and he promised to himself that he would make friends and never leave them like his did.
Winston is very loyal and caring friend which means he come off as clingy and strange. He would die for all of his friends, he believes that his life comes second after protecting his loved ones. However unless you threaten one his close friends he can get along with pretty much anyone, that is except bullies, he can't stand bullies.