This is what happened to the rebellious kid Bart Simpson in
Born in the Blue. He becomes one of the most influential Chief Justices of the Supreme Court.
In his father's presidency, he was viewed as an embarrassment, with his naughtiness hurting the First Family's image. Later, Bart would say that the stress of being the First Family hurt the family and that his acting out was his way of copying. After Homer stepped down in January 2017, Bart felt that he was liberated from the stress of the public eye. He was then 18 years old and chose to take a construction job "to work out the stress and anger I had". This job lasted five years, and after that, he fell by the wayside, his application to law school getting lost and he fell in poverty, taking on an amateur music career. In the end, he was bailed out by his dad, now an elder statesman, and got his application successfully accepted. "I felt that our relationship, once terrible, started to heal at that point. His act showed to me that he did indeed care for me and wished the best for my future."
His time in law school was good and he received his law degree. He ended up a lawyer, but by the 2040s, he developed a drinking problem due to his relationship with his wife ending in divorce and this caused him to lose his career as a result. This worsened his drinking problem, and by the time his sister became President, he fell back in his childhood role, that of being a presidential embarrassment.
However, in late 2045, Bart Simpson managed to use his law knowledge to help his sister's administration deal with a crisis, and dealt with his drinking problem. Thus in early 2046, after Harvey Dent resigned due to health issues, Bart was appointed Chief Justice of the Supreme Court.
His appointment was at first shocking as it was somewhat nepotistic, but he proved a very capable and even transformative Chief Justice, and by the time he stepped down, he was a widely-respected judge and his two kids became somewhat prominent in Ohioan politics, continuing the powerful Simpson political dynasty.