The lives of the last four presidents make an interesting contrast. The two Rs were both sons of already very rich and powerful fathers, and the sons had numerous catastrophes of their own making, several of which would have put them into prison and would have ruined anyone without a father who was fabulously wealthy and powerful.
On the other hand the last two D presidents lost their fathers early and were raised mainly by their mother, impressive women both, and both had stepfathers that were completely out of their lives by the time they went to college. Neither had much money and both got into and through the Ivy League entirely on their own merit.
Bill Clinton's father and stepfather were both salesmen. His father died in an auto accident before Bill was born and his mother remarried a few years later--this time to a car dealer. His mother was a waitress when Bill was born but became a nurse. Bill did very well in school and got into Georgetown, became a Rhodes Scholar and went to Oxford, and Yale Law School, where he met Hillary Rodham. Clinton opposed the Vietnam war and did not enlist, and due to a lucky high lottery number (311) was not drafted. He went into politics almost immediately after graduating from law school.
George W Bush's father was George Herbert Walker Bush, 41st president and himself the son of an important politician, Prescott Bush. His mother Barbara was descended from the brother of Franklin Pierce, 14th president. The Bushes had strong connections to the oil business. His father's connections got him enrolled in the Texas Air National Guard, where he learned to fly jets. He received low ratings as a pilot, and went AWOL in 1972 until he was discharged in 1974, but apparently due to his connections, was honorably discharged. He failed to get into law school, but did get into Yale business school, again, apparently because of his father. His grades were mediocre and he was a heavy drinker. Friends of his father set him up with an oil drilling company, which would never succeed but eventually would be bought out by another company, and George sold his shares and bought into the Texas Rangers baseball team. He would sell these shares for a 3000% profit while he was governor. His first political office was governor of Texas, and when he ran for president, he lost the popular vote by more than half a million votes, but won just barely enough electoral votes to get in, with a boost from Florida, where his margin was 500 votes, his brother was governor, and the secretary of state was his campaign manager, and there were tens of thousands of democratic votes suppressed.
Barack Obama's father was a talented student from Kenya who divorced his mother when he was 3. The last time young Barack saw his father was when he was ten. Obama Sr died a few years later. Obama Jr's mother, Stanley Ann Dunham, was an anthropology student from Kansas who would earn a masters degree while Barack was still young and a PhD while he was in college. Barack got into Columbia with a full scholarship and Harvard Law, where he was president of the Law Review. He would work as a law professor for a while before going into politics.
Donald Trump's father Fred was a very wealthy real estate tycoon in Queens, NY, who inherited the core of his business from his father. It seems that the brains of the outfit was actually Fred's mother. Fred was known to be ruthless and terribly racist and left in his wake mostly slums. Donald was big and strong and pretty wild , repeatedly beating up other kids to steal their lunch money. Trying to get him to behave, Fred would send him to military school, where Donald finally thrived, apparently because he was pretty good at running scams to get others to do things for him. A big, strong kid, he enjoyed baseball and other sports. He got into college, apparently, because he paid a smarter kid to take the SAT for him, and eventually got into UPenn and obtained an undergraduate degree in Economics, which he clearly knows almost nothing about. It's not clear he actually did much of the work for himself as he was absent for most of his senior year. He was a millionaire before he was 5 and his father gave him $5 million to start his own real estate business while he was still in college, and would eventually inherit his father's business. He had a small number of successes, but many, many failures. His father bailed him out many times, yet he went bankrupt at least 6 times. He also seems to have been further bailed out by money given to him by a division of Deutsche Bank which mainly deals with Russia, and many deals more directly with Russian oligarchs. His main source of income since his father died in 1999 seems to have been money laundering for Russians and his salary from his TV career and a series of frauds and cons. Don, born the same year as Clinton and Bush, got out of Vietnam service when a doctor said he had bone spurs in his feet. In his very first political election, Don lost the popular vote by nearly 3 million but won a narrow victory in the electoral college, strongly boosted by smears to his opponent that came from Russia and one from the FBI.
