He made a large fortune as a stock and commodity market investor, and later rolled over his proceeds by dedicating a substantial amount of his wealth into investment-grade real estate and a wide range of privately controlled businesses across the United States.

During his mid to late 20s, he made a large fortune as an active commodity and stock investor; he then reinvested much of his proceeds into film studios, real estate, and shipping lines.

[8] When Fortune magazine published its first list of the richest people in the United States in 1957, it placed Kennedy in the $200–400 million group, which is equivalent to roughly 3.2 billion dollars in 2023.

[14] Although he was skeptical of American involvement in World War I,[15] Kennedy sought to participate in wartime production as an assistant general manager of Fore River, a major Bethlehem Steel shipyard in Quincy, Massachusetts.

It is said that he knew it was time to get out of the market when he received stock tips from a shoe-shine boy, but no evidence has been found of the anecdote and the first known version of the same tale was associated to Bernard Baruch in 1957.

[32] In October 1928, he formally merged his film companies FBO and KAO to form Radio-Keith-Orpheum (RKO)[33] and made a large amount of money in the process.

[44][45] The most important purchase of his real estate investment career was marked by the land acquisition of the largest privately owned building in the country, Chicago's Merchandise Mart (the world's largest building at the time), which gave his family an important base in that city and an alliance with the Irish-American political leadership there to lay the groundwork for realizing his sons' future political ambitions.

First was to restore investor confidence in the securities market, which had collapsed on account of its questionability, and the external threats supposedly posed by anti-business elements in the Roosevelt administration.

Thirdly, and much more important than the frauds, the SEC had to end the million-dollar maneuvers in major corporations, whereby insiders with access to high-quality information about the company knew when to buy or sell their own securities.

The book had significant impact in the business community and after his re-election, Roosevelt appointed Kennedy as Chairman of the United States Maritime Commission,[53] which built on his wartime experience in running a major shipyard.

[13] Father Charles Coughlin, an Irish Canadian priest near Detroit, became the most prominent Roman Catholic spokesman on political and financial issues in the 1930s, with a radio audience that reached millions every week.

In 1936, Kennedy worked with Roosevelt, Bishop Francis Spellman and Cardinal Eugenio Pacelli (later Pope Pius XII) to shut Coughlin down.

In the spring of 1938...the couple luxuriated in the warmth of English hospitality, hobnobbing with aristocrats and royalty at the many balls, dinners, regattas, and derbies of the season.

The highlight was surely the April weekend that they spent at Windsor Castle, guests of King George VI and his wife, Queen Elizabeth.

[64]While getting dressed for an evening at Windsor Castle soon after he arrived, Kennedy paused in momentary reflection and remarked to his wife, "Well, Rose, this is a helluva long way from East Boston, isn't it?

[68] When war came in September 1939, Kennedy's public support for American neutrality conflicted with Roosevelt's increasing efforts to provide aid to Britain.

With German troops having overrun Poland, Denmark, Norway, Belgium, the Netherlands, Luxembourg, and France, and with daily bombings of Great Britain, Kennedy unambiguously and repeatedly stated that the war was not about saving democracy from National Socialism (Nazism) or from Fascism.

"[68] When Klemmer returned from a trip to Germany and reported the pattern of vandalism and assaults on Jews by Nazis, Kennedy responded, "Well, they brought it on themselves.

[75] According to Edward Renehan: As fiercely anti-Communist as they were anti-Semitic, Kennedy and Astor looked upon Adolf Hitler as a welcome solution to both of these "world problems" (Nancy's phrase).

Kennedy replied that he expected the "Jew media" in the United States to become a problem, that "Jewish pundits in New York and Los Angeles" were already making noises contrived to "set a match to the fuse of the world".

Biographer Laurence Leamer in The Kennedy Men: 1901–1963 reports: "Joe believed that Roosevelt, Churchill, the Jews, and their allies would manipulate America into approaching Armageddon.

[78] However, even during the darkest months of World War II, Kennedy remained "more wary of" prominent American Jews, such as Associate Justice Felix Frankfurter, than he was of Hitler.

[80]From late 1939 onwards, Kennedy began to suspect that Roosevelt and the State Department were excluding him from decision-making and communiqués pertinent to his ambassadorial duties.

[81] In early 1940, Roosevelt also sent personal representatives (under Secretary of State Sumner Welles, and General William Donovan) on fact-finding missions to London and other European capitals, without advising Kennedy beforehand, thereby causing the ambassador great embarrassment and annoyance.

Kennedy stayed active in the smaller venues of rallying Irish-American and Roman Catholic Democrats to vote for Roosevelt's re-election for a fourth term in 1944.

In 1960, Joe Kennedy approached Nixon, praised his anti-Communism, and said "Dick, if my boy can't make it, I'm for you" for the presidential election that year.

In return, Congressman John F. Kennedy, running for the Senate seat, would not give any anti-McCarthy speeches that his liberal supporters wanted to hear.

[91] Kennedy had been consigned to the political shadows after his remarks during World War II ("Democracy is finished"), and he remained an intensely controversial figure among U.S. citizens because of his suspect business credentials, his Roman Catholicism, his opposition to Roosevelt's foreign policy, and his support for Joseph McCarthy.

[99] As Kennedy's business success expanded, he and his family lived in increasing prosperity in Massachusetts, New York, around Washington, D.C., London, as well as the French Riviera.

[112]) Rosemary's erratic behavior frustrated her parents; her father was especially worried that she would shame and embarrass the family and damage his political career and that of his other children.