Hamilton has a thing for artists, so one day he goes to a park and sees a girl weaving (flower crowns, baskets etc.) , & a boy drawing sitting on a fountain edge looking at turtles in the fountain . Later in life he meets a girl who spray paints, they get arrested together and Hamilton loses all chances of getting into the college he wanted
Spray paint girl is Maria
Drawing boy is John
Guitar girl is Eliza.
The college is his chance at a presidency.
The reason Maria also goes to jail is because she was shunned for a
majority of her life after Hamilton while being abandoned by her husband
and Hamilton (who she might have loved)