Jack Winston is the second of Steve and Carla Winston's three children. As the middle child, Jack often felt alienated and not included, and he began acting out at an early age because of it. His parents thought he was mentally unstable and put him through various medical testing and psychiatric evaluations. When nothing was found to be wrong with him, his father begrudgingly let it go, though he was never convinced of his son's mental stability. That only made Jack feel less wanted, and he barely said a word to his family from the age of ten on.
Jack took to karate classes and video games to distract himself from the lack of love he felt in his household. He filled his mind with fantasies of escaping a life without love and finding a new family. He knew that as soon as he was able, he was going to leave home and move to the United States. He wanted to get as far away from the negativity as possible. His mother's dual citizenship made it easy for him to become a legal citizen once he turned 18, and it was straight off to college in California.
He had a dream of being a hero to all, and that dream led him to decide on a degree in Criminal Justice. While the degree wasn't needed to become a cop, he wanted to blow the other applicants away once he did apply. His lack in self-confidence made him feel the need to really prove himself to others, and he made very few friends during his years in California because that trait was mistaken for cockiness.
He eventually found himself in Massachusetts working for the state police. He showed great promise, and it was that promise that led to him being picked to go undercover. He has two undercover operations under his belt and started his third in late 2013. The pressure of doing well has started to get to him, and he has made his fari share of bad decisions. Because of how deep his cover had gotten at Lolita, his supervisors refused to pull him out in hopes that he would get himself killed to make their lives easier.
That would not be the case, however. As 2014 went on, Jack began to feel more and more conflicted about his job. He began to realize the corruption within his unit ran deeper than he could have imagined; it didn't help that he was slowly, but surely, falling for the woman he was supposed to be investigating. By the end of the year, he had finally resigned his position with the police and moved into a full time position as Lolita's head chef. As a further middle finger to his former employers, he also began working for the very mob he had been made to investigate – but he did a lot to turn his deeds into more of a Robin Hood operation.
Even though the relationship with his boss eventually ended, Jack has no regrets about leaving his former job behind. Cooking, it turns out, was what he was made to do. In the summer of 2015, he dove into a business endeavor a good friend, which would not have been possible without the income from his shadier dealings. The two opened a video game bar, appropriately named In Another Castle; the business has seen moderate success and continues to grow.
His love life took a turn when he began to realize feelings for a longtime friend. As it turned out, those feelings were reciprocated, and the two fell into a wild romance. Within a year, he had proposed, and the two were married on July 15, 2017. He and Roxy tried for months to concieve children, and after a few false alarms, they were successful. On June 4, 2018, they welcomed identical twin girls, named Whitney Anne and Winifred Eleanor.