Hugh was born to Martha and Maxwell Shapiro in Houston, Texas on April 9, 2001. He has two brothers and two sisters, all older, and Hugh is the only one still living at home.

When Hugh's father was transferred to Oxford for his job, Martha was not happy. The daughter and only heir of a wealthy Texas oilman, Hugh's mother pushed back against the move, reminding Maxwell that her parents had left her well provided for and he didn't need to work at all, much less relocate to Mississippi.

But Maxwell was committed to his job and wasn't willing to live off his father-in-law's estate, so Maxwell, Martha, and Hugh moved to Oxford in 2016 in spite of Martha's protests. Since their arrival in town, Martha regularly makes her dissatisfaction known to her family and is already planning their eventual return to Houston.

The other Shapiro children stayed behind in Texas. They have never come to Oxford because they find it hard to stomach their mother's attitude since the move. They keep in touch with Hugh online and regularly invite him to visit them back home in Texas.

After the Shapiros arrived in Oxford, Hugh tried out for the cheer squad at the start of the next school year even though Yoknapatawpha High School had never had a male cheerleader before. The cheerleading team at his old school was co-ed, and he fought to be allowed to try out for this one. The coach was impressed with his ability and quickly added him to the squad.

Some of the more traditional members of the community were dismayed to see a male cheerleader, and Hugh's mother was mortified that he'd made such a spectacle of himself when they were so new in this small town. Hugh's father, on the other hand, was proud of his son for going after what he wanted and breaking new ground.

Hugh loves cheering and is exceptionally talented at it. Coach Puskus saw how well Hugh and Katy Brown complemented each other's skills and paired them for some of the more difficult acrobatic stunts. As a result, Hugh and Katy spent a lot of time together practicing.

Classmates claim Hugh was infatuated with Katy, but he has always denied it, telling anybody who asked that a romantic relationship with anyone on the squad would be bad for the team and he would never even consider it.

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