The Singer

Alan J. Schwarz
5 min readFeb 4, 2020

‘’Shadow’’ was an interesting character. His Mother’s side of the family were all Jewish, including an Uncle who was a Rabbi. His Father’s side were Baptists, who grew up in the deep South. They had embraced Gospel music and one of Shadow’s Aunts, was the famous Gospel singer, Lucinda Stevens.

Growing up had been an interesting experience for Shadow, real name Leonard Wexton, as he had spent most of his early childhood living in a not great section of Toronto. His Mother, Esther loved him very much and worked hard to provide a comfortable home but it was not easy. Leonard’s Dad had split early in the marriage and Esther raised him alone.

Shadow’s Grandparents in Toronto were affluent, but Esther was a proud, rebellious woman and didn’t want to move in with them, she wanted to prove she could make it on her own.

Things were tough and got tougher when a gang tried to recruit twelve year old Leonard to join them or face the consequences. He told his Mother, and she actually went and confronted the sixteen year old ‘’leader’’ of the gang, telling him to leave her son alone. When he laughed in her face, she knew it was time to get out of dodge.

Esther’s Mom and Dad welcomed Esther and Leonard with open arms and enrolled Leonard in a local high school, Forest Hill Collegiate. It was not an easy transition and Leonard actually found himself missing his old friends. He worried about the ones who were leaning towards gang life, cause he knew what that meant. Once you were in the gang, there were ‘’initiations’’ and it was almost impossible to get out.

At his school there was two Jewish boys who gave Leonard a hard time for no real reason. Bobby Newman and Joel Sinder excluded him from parties and never invited him to play sports or just hang out like they did with other kids. When they had their Bar Mitzvahs they invited everybody in their class except Leonard. It was crushing.

Leonard’s life changed for the better when his drama teacher, Mrs. Cohen suggested she had a great opportunity for him. Her Brother, the famous Director Frank Cohen was Producing and Directing a feature in Toronto and he had a small role for a teenager. She thought he’d be perfect. He would get to go on a movie set, he’d get paid very well, and he’d experience acting and she thought he’d be a natural and do very well. Mrs. Cohen was always encouraging him.

Leonard ran home to tell his Mom and his Grandparents and they were excited and delighted for him. ‘’I promise you, once I do this movie, I’m going to become a major star.’’ Leonard left the house with a new found sense of confidence.

The role Leonard had was micro but he got to say two lines and they both worked so well that all kinds of positive attention was heaped on him. The lines were ‘’You want to be somebody else, I know you think I can’t do anything cause I’m a kid, but on the internet I can turn you into Superman.’’ His second line which received all kinds of critical acclaim and stood out was ‘’In life you gotta choose your direction, I know I’m a kid but I also I know I can tell the difference between right and wrong, and man you’re choosing wrong.’’

Before he knew it Leonard was being approached by Agents and the film went blockbuster. Leonard however had a secret. He enjoyed acting but his real passion was singing and rap. He wrote thousands of rap songs and when he signed with a theatrical representative from CAA, he told her his real passion was music not acting. She put him in touch with an Agent in the music division and ‘’Shadows’’ career took off. Before long acting was an after thought and he began rapping in different music venues and his songs became popular downloads, scoring millions of listeners. His music videos were watched by tens of millions of people and he became a huge sensation.

His Grandfather, Morris passed, and Leonard became extremely close with his Bubbie, who he loved with a passion. She was so proud seeing him play sold out concert halls around the world. He bought his Mom a fantastic mansion, and he reconnected with his absentee Father and they became friends.

In a couple of songs he mentioned how much he despised two guys named Bobby and Joel but they were probably the only two in the world that knew he was directing his animosity at them personally.

Life was absolutely amazing, Leonard or Shadow his stage name, became the face and voice of Toronto. When he referred to Toronto as TDot in one of his songs, that’s what the world started calling the city.

Leonard was omnipresent at Toronto Hockey games, Basketball games and Baseball games. He gave impromptu concerts for the city, and he built himself a forty million dollar mansion in Forest Hills. He was the symbol of success.

Yet there was one thing that Shadow wouldn’t do. He never played or visited Israel and when Antisemitism flourished in New York he never used his star status to try and calm the situation down by explaining that hate against the Jews was wrong. That the Black community and Jewish community had more similarities than differences. He never stood up for the Jewish people which was disappointing. He had the platform and the power but he abdicated any and all of those responsibilities.

Mrs. Cohen and his Bubbie always wanted to believe that Leonard would use his world wide appeal for good. That he would embrace and support his Jewish background, but the only thing he did was create a song and make fun of his Bar Mitzvah experience. His Bubbie told a friend ‘’When you love your Grandchild unconditionally, you don’t scold or alienate when they don’t do what you wish they’d do. Instead you just show support and love. Leonard needs real love and there’s only a few people who he can trust.’’

Shadow continues to be a favourite around the world, he continues to fill stadiums, release number one albums, and reach millions around the world with his music videos. He has also has never publicly supported Israel or the Jewish people when they were going through rough times.

In an interview Shadow was asked about his philosophy of life. He talked about his friendship with people like basketball great LeBron James, and Rhianna, and how much he cared about them. His exact words were ‘’I love my friends and never want to do anything to alienate them. I know what’s cool and what’s not cool, and you’ll always find me on the cool side.’’

When his Bubbie heard Leonard’s interview a tear rolled down her face and she regretted that supporting the Jewish people and Israel were not considered cool in her Grandson’s eyes. Somewhere along the way she and her daughter Esther had failed him. No matter how successful he had become his priorities were skewed and for that she felt a tremendous sense of sadness and disappointment. She loved Leonard with her heart and soul she just wished she would have instilled more Jewish pride in him. It was something she would regret forever no matter how popular he had become.



Alan J. Schwarz

Alan Schwarz loves life. He is the founder of JAMS Productions, a television production company based in Toronto . His passion is writing.