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 His became very depressed and withdrawn, his friends tried to coax him out of his shell, eventually it worked.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 had a pretty uneventful time at Hogwarts until his fourth year. He took his best friend to the Yule Ball but they both found out quickly that there was nothing there. Unfortunately for Winston she left mid-way through fourth year... right when he needed her most.
Winston's mom had committed suicide. She had finally given up on life, Winston was confused. Since coming to Hogwarts he had basically been taking care of Gwen and his mom, so he was relieved he didn't have to deal with that anymore but at the same time... he was now an orphan.
Winston and his sister moved in with his their Aunt and Uncle, but despite how much they care for Winston, it doesn't feel like home to him so he avoids it much as he can. He cares for his Aunt, Uncle and Cousin, he just doesn't feel at home with them. So he's planning on moving out as soon as he can.
In his fifth year, Winston me a girl his age named Melody Padmore. After a dance lesson gone wonderfully wrong the pair went on a date and were soon dating. In their seventh year they were chosen to be Head Boy and Girl. Their relationship only got stronger by working together as the most senior students.