Jessie's parents divorced when she was 3 and her biological father left town never to be heard of again. Her mother was a social worker and raised Jessie in a low income, racially diverse neighborhood where she taught her daughter the beauty of diversity.
After cheering in high school, she went on to college and emerged as the life of the party anywhere she went. To supplement her scholarships, she worked as a server to pay the bills. It was at that college job where she met James O'Neil who was managing the same restaurant that Simon, Amelio and Peyton were working. She never took James' bi-polar nature seriously, so James took a liking to her and she won over his trust.
It was also during that time that her mother died of breast cancer and it plunged her into a phase of intense partying. One night she had too much and Amelio tried to get her to go home and sleep it off, but she refused. This led to the birth of her daughter and changed the course of her life. She dropped out of college and went to work at the restaurant full time.
When James decided to open "O'Neils Irish Pub and Restaurant" he asked Jessie to come on as the head waitress. She accepted on the condition that she could choose the work crew. James agreed, but told her he needed positions for his daughter and his niece, and also asked her to "keep it cheap," accompanied by a wink.
So Jessie asked Simon to manage the dining area and in turn, further his American dream. She asked Peyton to run the bar, and Amelio to head up the kitchen. She also had a good friend from high school whose nickname was Guerro, and she asked him to join the crew as the head dishwasher. Finally, she had recently met a friend of Amelio who was a server at another restaurant, Santiago. She asked him to come on and be the head waiter. Santiago told her of a few others who could fill in the remaining spots, and that's how the crew was put together.