P. J. and Mary wanted the best for their son. When he was thirteen they enrolled him in the prestigious Boston Latin School, a main training ground for future Harvard students. Joseph was one of the few Catholics at the Protestant school. Although he got along with his classmates and was even elected class president, he struggled in his class work. He had good instincts and street smarts, but academics were often beyond him. He was proficient in mathematics, but he was unable to master advanced subjects such as geometry. After failing physics, Latin, and French in his junior year, he was forced to repeat the grade. Joseph's difficulties in school made him all the more determined to prove he would be a success.

Harvard Bound

Like his father, Joseph did not drink alcohol. In fact, his favorite beverage was milk. He eschewed coffee and cigarettes as well. When he graduated from Boston Latin, his goal was simple: to be rich. But his parents insisted he go to college first. He applied to Harvard, considered the best Ivy League school. Despite his mediocre grades, Joe was accepted — partly because of family connections but also because of his perceived potential. P. J.'s son just seemed destined to be an important man. The fact that he was also the leading hitter in Boston's high school baseball league didn't hurt, either.

Not surprisingly, Joe also struggled academically at Harvard. To make sure he graduated, he chose musical appreciation as his major. Throughout his college career, Joe never stopped making money. He and his friend Joe Donovan bought a used bus for $600 and started a sightseeing business during summer vacations. They sold tickets at the city's main railroad terminal for excursions to the historical sites at Lexington and Concord, where the first battles of the Revolutionary War were fought. Selling tickets required a permit, which P. J. made sure his son received.

Joe's college experience further inflamed his determination to succeed. Initially, Joe enjoyed his life at Harvard, assuming he would be as accepted there as he had been at Boston Latin. But he soon learned that Catholics were not always welcome into the elite clubs that many of his friends belonged to. It was a devastating experience that informed the rest of his life.

Business Savvy

When Joe Kennedy graduated from Harvard, he promised his friends he'd be a millionaire by the time he was thirty-five. As usual, P. J. paved the way. In 1912 he got his son hired as a bank examiner for the state of Massachusetts. The job gave Joe access to confidential information about the banks' financial holdings and business plans. He used this information to buy and sell stocks for personal gain — what today would be called insider trading, a federal offense. He invested $1,000 in an investment company called Old Colony Realty Associates that took over the mortgages on homes that had defaulted — again, information obtained while he was a state examiner. He would cosmetically fix up the houses with a coat of paint, then resell them for significant profits. When he dissolved the company, he had made more than $75,000 off his initial investment.