The Curious Relationship of Joseph Kennedy, Sr. and Franklin D. Roosevelt

The Curious Relationship of Joseph Kennedy, Sr. and Franklin D. Roosevelt

Larry Holzwarth - November 24, 2019

Joseph Kennedy Sr. first met with Franklin D. Roosevelt when the latter was serving as Assistant Secretary of the Navy during the First World War. Kennedy had taken a position at the Fore River Shipyard at Quincy Point, Massachusetts. Kennedy didn’t need to work at the shipyard, he was already quite well-to-do from his successful investments in real estate and banking, but he wanted to support the American war effort, with an eye on a future political career. As an assistant supervisor, he was a member of a construction effort which delivered more than 70 destroyers to the US Navy over the course of the war.

The Curious Relationship of Joseph Kennedy, Sr. and Franklin D. Roosevelt
Rose and Joseph P. Kennedy in November, 1940. Wikimedia

Though he and FDR did not work closely together during World War One, subsequent events would bring them together again during the Great Depression. By then both men were well known for their wealth and the image of privilege which surrounded them. FDR, an athletic man during the First World War, had been stricken with polio and confined to a wheelchair. Kennedy was known for his affairs with Hollywood starlets, his real estate empire, and his uncanny ability to make huge sums of money through the stock market, all through the 1920s. Roosevelt had need of his services, and Kennedy had need of a political patron. Neither got exactly what they wanted.

The Curious Relationship of Joseph Kennedy, Sr. and Franklin D. Roosevelt
John F. Fitzgerald, known as Honey Fitz, was Joseph Kennedy’s father-in-law and political patron. Wikimedia

1. Kennedy was born into a financially comfortable Boston family

Joe Kennedy’s father was a successful saloon owner and real estate investor when Joe was born, and though the family was shunned by Boston society for being Irish, they were financially well off. Joe was an indifferent student, though popular and athletic, and entered Harvard College, at which he lobbied hard to join the Hasty Pudding Club and played on the school’s baseball team. When he graduated it was with a bachelor’s degree in economics, in 1912. Two years later he surrendered his status as a bachelor when he married Rose, the daughter of John Fitzgerald, the mayor of Boston known by his nickname, Honey Fitz.

Following his graduation from Harvard, Kennedy first worked as an employee of the Commonwealth, serving as a bank examiner. His sharp eye for opportunity and astute financial judgment, as well as what in a later day, came to be called inside information presented him with his first business coup. Aware that Columbia Trust Bank was about to be taken over he borrowed the equivalent of $1.1 million dollars and purchased control of the bank, installing himself as its president, through an election held among the shareholders. He was just 25 at the time, and he boasted that he was the youngest bank president in the United States, an unconfirmed piece of bravado.

The Curious Relationship of Joseph Kennedy, Sr. and Franklin D. Roosevelt
Joseph P. Kennedy was a bank president at the age of just 25. JFK Presidential Library

2. Joe Kennedy began investing in real estate while still working as a bank examiner

Kennedy’s position as a state bank examiner allowed him access to information which was nearly priceless from a standpoint as an investor. Examination of bank records gave him information on the financial condition of depositors, the status of mortgages and other loans, and which companies had been developing new products and services ready to bring to market. He bought control of a real estate firm in Boston called Old Colony Realty Associates. Through it, he purchased financially distressed properties in or near foreclosure, and resold them profitably. His investment in the firm paid substantial dividends.

The real estate investments led to a growing interest in the stock market following the First World War. The decade known as the Roaring Twenties, was a period during which many still believe and repeat that Kennedy was a bootlegger. There is simply no physical evidence that Kennedy participated in the illegal liquor trade, and the anecdotal evidence is all based on questionable sources. The stories didn’t begin to appear until the 1950s. During the 1930s, Kennedy was thrice confirmed by the Senate for government positions, following an investigation into his background, conducted by committees which included politicians’ hostile to the president. None of the committee records show any evidence he was suspected of bootlegging.

The Curious Relationship of Joseph Kennedy, Sr. and Franklin D. Roosevelt
Kennedy was present but uninjured when a bomb struck Wall Street in 1920. Wikimedia

3. Manipulating the stock market was routine before the 1929 crash

Following the war, Kennedy joined the Boston brokerage firm of Hayden, Stone and Company. Stock manipulation, insider trading, and other activities later made illegal were all perfectly legal at the time, and astute brokers learned to recognize the signs when some entity was “playing the market”. Kennedy was in New York at the corner of Broad Street and Wall when a bomb exploded nearby on September 16, 1920. He was thrown to the ground by the force of the blast, but emerged uninjured. Italian anarchists were suspected, but the bombing has never been solved. Kennedy remained with Hayden, Stone until 1923.

While there he learned the methods of manipulating the market, driving down stock prices to purchase at lows, and driving them up to sell high. Journalists were often bribed to provide inaccurate information to the public. Pools were formed through which groups of investors controlled the activity of stock, with members of the pools reaping the profits. Kennedy left Hayden, Stone and Company in 1923, creating his own investment company. The large profits he made allowed him to become a major donor to the Democratic Party, which caught the attention of senior party officials. By then he was ready to invest in the booming film industry.

The Curious Relationship of Joseph Kennedy, Sr. and Franklin D. Roosevelt
Actress Gloria Swanson was one of many women with whom Kennedy conducted extramarital affairs throughout his life. Library of Congress

4. Kennedy moved to Hollywood to make movies

Kennedy began investing in small movie studios while working as a broker, and in 1926 he moved to Hollywood, to acquire and operate movie studios and invest in films. In the 1920s film studios also owned, through subsidiaries, movie theater chains which showed their films. Kennedy executed a hostile takeover of one such chain, Keith – Albee – Orpheum Theaters Corporation (KAO). The over 700 theaters acquired were in many cases vaudeville houses, which were converted to movie theaters. Kennedy merged his film interests into a new company, Ralph – Keith – Orpheum (RKO) in 1928 in a deal in which he pocketed a large profit through the manipulation of the stocks involved.

During his period of investing in Hollywood Kennedy made an estimated $73 million in today’s money. His brash interactions with the press, particularly Hearst Newspapers, made him nationally famous. He also carried on an affair with the glamorous actress Gloria Swanson for more than three years. She was not his only indiscretion. Most of the money Kennedy made in Hollywood was invested in real estate, including Hialeah Race Track in Florida, the Chicago Merchandise Mart – then the largest building in the world – and commercial properties in New York and Boston. In 1929 the stock market crashed, but Kennedy’s fortune remained intact, and even expanded during the Great Depression.

The Curious Relationship of Joseph Kennedy, Sr. and Franklin D. Roosevelt
Franklin Roosevelt steadies himself on the arm of his son James, a supporter of Kennedy’s. Wikimedia

5. Democratic Party politics brought Kennedy together with James Roosevelt, FDR’s son

During the 1932 presidential campaign, James Roosevelt served as FDR’s deputy in Massachusetts, where he had established a successful business in Boston. James became a protégé of Kennedy’s who helped guide him through the maze of Democratic alliances, and the Irish politics of Boston. James made more than 200 campaign appearances in Massachusetts on behalf of his father, who had lost the Democratic Primary in the state when the Irish Catholic vote largely went for Alfred E. Smith. Kennedy’s backing, both with money and in appearances, helped FDR appear more attractive to the Irish Catholic vote, and FDR carried the state in November.

Joe Kennedy and James Roosevelt then went to the United Kingdom, having formed a corporation called Somerset Importers. They carried with them licenses to import alcohol in limited quantities for medicinal purposes, legal under prohibition. In the UK they negotiated exclusive US distribution rights for several UK brands of scotch and gin, which began to be shipped into the United States when Prohibition ended in 1933 (the amendment was ratified before Kennedy returned). Kennedy again used information and connections to corner a large portion of the legal liquor market after Prohibition was no longer the law of the land.

The Curious Relationship of Joseph Kennedy, Sr. and Franklin D. Roosevelt
Roosevelt was reluctant to appoint Kennedy to head the SEC, but was persuaded by advisors including his son James. FDR Presidential Library

6. Kennedy wanted a role in the Roosevelt Administration, and FDR found him one

In 1933, Roosevelt hastily passed a series of New Deal programs including among many the Securities Act of 1933. It offered some protections for investors, but lacked the enforcement mechanism necessary to ensure that the kind of manipulation and insider trading, as well as the propagation of false information to potential investors, was curtailed. The following year Congress passed the Securities Exchange Act of 1934. It established an enforcement arm for control of the nation’s financial markets, granted the authority to monitor trading and investigate irregularities, as well as the authority to subpoena witnesses and participants.

When FDR asked his advisors their recommendations of who was to lead the new agency, which was to be one of the most powerful of the federal government, he was provided a list, with Kennedy’s name at the top, “because of executive ability, knowledge of habits and customs of business to be regulated and ability to moderate different points of view on Commission”. FDR supposedly likened the appointment of Kennedy as an example of the adage “set a thief to catch a thief” though there are many different versions of the quote, in different times and places, and whether the president actually made the comment first is questionable, though the observation was certainly apt.

The Curious Relationship of Joseph Kennedy, Sr. and Franklin D. Roosevelt
Wall Street financiers opposed the creation of the SEC, claiming they could regulate themselves. Wikimedia

7. Kennedy absorbed attacks which had been earlier directed toward Roosevelt

Richard Whitney became President of the New York Stock Exchange in 1930, serving in that role until 1935. He was one of the most vocal opponents of federal oversight of the exchanges, and established a base in Washington of like-minded financial leaders to fight the bill which created the SEC while it was debated in congress. They established themselves in a Georgetown building which became known in the press as the “Wall Street Embassy”. Arguing that Wall Street and the nation would be better off if it was allowed to regulate itself, they presented the bill as the forefront of communism in America’s financial system, and that it would prevent the economic recovery desired.

In truth, Roosevelt wavered over the appointment of Kennedy to the position for political reasons. He asked a Democratic operative, Frank Walker, to convince Kennedy to turn down the appointment. Kennedy, who was already disappointed that he had not been appointed to the President’s cabinet as Secretary of the Treasury, refused to withdraw his name. After political maneuvering among the President’s advisors and allies, as well as attacks from several opponents, including Scripps Newspapers, Kennedy was selected, subject to confirmation by the Senate. It was then up to Kennedy to bring to Wall Street the changed realities of American investments.

The Curious Relationship of Joseph Kennedy, Sr. and Franklin D. Roosevelt
A crowd outside of the New York Stock Exchange in 1929 following the crash which triggered the Great Depression. Wikimedia

8. Kennedy won widespread praise for the reforms he established in the exchanges

When Kennedy entered the office of Chairman of the Securities and Exchange Commission it was under a six-month probationary period, after which he would be confirmed by the Senate or dismissed. In 1935 the Washington Post reported, “Kennedy has done one of the best jobs of anyone connected with the New Deal and has done it without bluster or publicity-seeking…” Editor John T. Flynn of the New Republic, one of the harshest critics of Kennedy receiving the appointment, changed his mind and called Kennedy one of the most useful members of the commission. Praise came from Wall Street as well, according to the Wall Street Journal in 1935.

Kennedy drew a larger wake through the Roosevelt Administration than the public realized. His success in creating and implementing the new regulations and safeguards in the nation’s exchanges reflected well on the man who appointed him – FDR. The president, beset with difficulties in several of the New Deal programs, began to frequently call on Kennedy for advice on issues, or to ask him to troubleshoot difficulties as they arose. Kennedy was at the White House (or Roosevelt visited him at his nearby estate) several times per week. He was widely considered a rising star within the Democratic Party, though for the time Roosevelt needed him where he was.

The Curious Relationship of Joseph Kennedy, Sr. and Franklin D. Roosevelt
Catholic priest Charles Coughlin was an antisemitic demagogue broadcasting a nationwide radio program in the 1930s. Wikimedia

9. Silencing Father Coughlin was a tasked FDR assigned to Kennedy

Father Charles Coughlin was a former FDR supporter who turned against the president in 1934, excoriating him on radio broadcasts and newspapers and magazine articles as a “tool of the rich”. By 1934 Coughlin was broadcasting to his large audience, many of whom were Catholic and all of whom were far-right, antisemitic messages which also demanded the federal government nationalize the railroads, the financial industry, communications, and other industries. Near the end of the decade Coughlin, who like Kennedy was Irish-Catholic, was supporting many of the policies of the Nazis and the Fascists in Europe.

After Kennedy warned the president that Coughlin was becoming “very dangerous” FDR tasked him with finding a way to silence him. Kennedy approached then Auxiliary Bishop of Boston, Francis Spellman, who in turn contacted Cardinal Eugenio Pacelli, Secretary of State for the Vatican. Coughlin was finally silenced through a combination of Church orders and changes to broadcast licensing regulations which deemed the airwaves a “limited national resource”, regulated as publicly owned. Cardinal Pacelli later was elevated to the papacy, serving as Pope Pius XII.

The Curious Relationship of Joseph Kennedy, Sr. and Franklin D. Roosevelt
Huey Long leaving the Senate after successfully filibustering one of FDR’s measures in 1935. Wikimedia

10. The New Deal created a wave of hatred among the press and the Congress

One of the nation’s most influential newspapers during the Great Depression years and beyond was the Chicago Tribune, run by Robert McCormick. McCormick despised Roosevelt, the New Deal, government regulation of Wall Street, and American intervention in European affairs. He supported the America First Movement and anybody who attacked Roosevelt. He was one of a legion of right-wingers who had the opportunity to attack Roosevelt through Kennedy by revealing illegal activities committed by the latter, yet he did not. There was simply no evidence to support such attacks.

Huey Long was another who would have seized the evidence of a Roosevelt administration official having committed illegal acts, though his attacks would have been launched from the far left. Though Long was far to the left he became an ally of Father Coughlin in the 1930s. Long wanted a system he dubbed Share our Wealth adopted, in which taxes on individual net assets would be collected and distributed equally to those most distressed by homelessness and unemployment. Hatred for Roosevelt (and Kennedy) was so strong that it reverberates in articles and websites in the 21st century.

The Curious Relationship of Joseph Kennedy, Sr. and Franklin D. Roosevelt
SS America under construction in 1939, a project of the Maritime Commission. Wikimedia

11. The United States Maritime Commission

In 1936 Congress passed and Roosevelt signed into law the Merchant Marine Act of 1936, which created the United States Maritime Commission. FDR was interested in improving and modernizing America’s shipping industry, and his experience as Assistant Secretary of the Navy during World War One, when Kennedy had worked at Fore River Shipyard, impelled him to appoint Kennedy to the post of Chairman. The commission was established to monitor and modernize shipping and warehouse facilities in ports, shipyards, and their support facilities. The commission was also tasked with modernizing regulations and practices. Kennedy accepted the post.

One of the features of the Maritime Commission, included as part of the Second New Deal, was the authority to design and build 500 new ships, of several designs, over a period of ten years. Oilers, tankers, cargo ships, and passenger liners were all included, one of them being the transoceanic steamer SS America, which served in that capacity before being converted to a troopship during World War II. Both the US Navy and the US Merchant Marine were favorites of Roosevelt, who gave them his special attention, and his appointment of the post of Chairman was an indication of just how far Kennedy had risen in the president’s esteem over the course of his first term.

The Curious Relationship of Joseph Kennedy, Sr. and Franklin D. Roosevelt
Joseph P. Kennedy Sr. in 1938, the year he was appointed Ambassador to Grear Britain. Wikimedia

12. Kennedy began to consider running for president in 1940

At the middle of Roosevelt’s second term, he had not yet indicated he would run for a third term in 1940. Leading Democrats began to jockey for position as the heir apparent, Kennedy among them. An appraisal of his resume revealed two weaknesses, one of which he could do little about. He was an Irish Catholic, and the nation had not to that time elected either. He also had little experience in foreign affairs, or with dealing officially with foreign governments. He did have some familiarity with leading British politicians, from his business dealings in England and Scotland in early 1933. He began to lobby Roosevelt for the appointment as Ambassador to the Court of St. James.

As the American representative at the Court of St. James, Kennedy would be able to monitor the situation in Europe, as well as gain extensive exposure to the government of Great Britain. The position was considered the most prestigious of the American Foreign Service, and Roosevelt appointed Kennedy to the post in 1938. Kennedy was at the time fifty years old, a millionaire many times over (he had established by then $1 million trusts for each of his nine children) and the first Irish American to be awarded the post. Once again the Senate confirmed his assignment, and Kennedy and his large family sailed to England to represent the interests of the United States.

The Curious Relationship of Joseph Kennedy, Sr. and Franklin D. Roosevelt
King George VI received the new Ambassador from America, who supported the policyof his Prime Minister appeasing the Nazis. Wikimedia

13. England was divided over the Nazis in Germany when Kennedy arrived

In 1938 King George VI was in the second year of his reign, and his government was run by Prime Minister Neville Chamberlain. Chamberlain maintained a coalition which was largely concerned with the manner in which Great Britain and its Empire confronted the expansion of the German Reich in Europe. Hitler had revealed the German Luftwaffe to the world, renounced the treaty of Versailles, and had begun his acquisition of territories in Europe with German populations. Kennedy arrived in Great Britain in March, 1938. He found a British government focused on the policy of appeasing the territorial demands of the German dictator.

Earlier in the month, Kennedy took up his post, Great Britain conveyed an offer to Germany proposing a European consortium to rule Africa, with Germany taking a leading role. The offer was contingent upon Hitler agreeing to maintain the current borders within Europe. Hitler declined. The annexation of Austria took place just over a week later. Throughout the summer Kennedy attempted, through the British Ambassador to Germany, Nevile Henderson, to arrange a personal meeting with Hitler, which the German dictator also declined. War clouds gathered over the summer during the negotiations over Czechoslovakia, with French and Czech troops mobilizing in August.

The Curious Relationship of Joseph Kennedy, Sr. and Franklin D. Roosevelt
Neville Chamberlain adopted a policy of appeasement dealing with German territorial expansion in Europe. Wikimedia

14. Kennedy supported the British Prime Minister’s position of appeasement

Whether Roosevelt knew of Kennedy’s attempts to arrange a meeting with Hitler at the time is unknown, but the American Ambassador to Germany, Hugh R. Wilson, was pro-Nazi and made several remarks to the American press praising Hitler. He also claimed Jewish influence in the American press was exaggerating the antisemitic activities of the Nazis, a position with to which Kennedy agreed privately. The Ambassador joined in with a group which called themselves the Cliveden Set, named for the home of Lady Nancy Astor, where they frequently met. Kennedy wrote to Lady Astor of his concern about “Jewish pundits in New York and Los Angeles”.

In May 1938, Kennedy met informally with the German Ambassador to Great Britain, Herbert von Dirksen. The talks were informal in that they had not been approved by the State Department. During the conversation, Kennedy explained that FDR’s position over the Nazis was skewed by Jewish influence, which kept the president misinformed over the true intentions of the Nazi Party and Adolf Hitler. Ambassador Dirksen informed Joaquin von Ribbentrop that Kennedy was Germany’s “best friend” in London, who would continue to support appeasement policies as Hitler moved forward to seize the Sudetenland in Czechoslovakia.

The Curious Relationship of Joseph Kennedy, Sr. and Franklin D. Roosevelt
Joseph P. Kennedy Jr. agreed with his father’s view regarding the Jews in Germany and the United States prior to WW 2. JFK Presidential Library

15. Kennedy grew controversial in the American press

As Kennedy continued to support appeasement and presented the achievements of the Nazis in the recovering German economy, he ignored the Jewish situation unfolding in Germany. Roosevelt was hampered in his efforts to address the increasing harshness of antisemitic laws by his ineffective representation in Germany and in Great Britain. Both ambassadors believed the Germans were justified in removing Jewish people from civil service and other positions, and Joe Kennedy Sr. shared his views with his son, Joe Jr. The latter wrote after touring Germany, “The dislike of the Jews, however, was well-founded. They were at the heads of all big-business…”

The father responded in kind, informing his son that the majority of the critical attacks of his position (75%) were from “Jewish publishers and writers”, who, “in their zeal did not hesitate to resort to slander and falsehood to achieve their aims”. Kennedy was aware by the time of Munich (September, 1938) that Roosevelt was losing patience with him, and told a British reporter that he believed that Roosevelt would be out of office following the election of 1940. He added, “The Democratic policy of the United States is a Jewish production”, in reference to his political party, rather than the form of government.

The Curious Relationship of Joseph Kennedy, Sr. and Franklin D. Roosevelt
The site of a synagogue destroyed during Kristallnacht. Wikimedia

16. The aftermath of Kristallnacht Kennedy clarified his position

Following the anti-Jewish rioting and destruction known as Kristallnacht, Roosevelt deferred a question on November 11 regarding America’s response to the State Department. At the time he was not yet fully informed of the extent of the violence and destruction which had occurred in Germany. On November 15, at another informal press conference (which he held nearly every day he was in the White House), he responded by announcing the American Ambassador to Germany was being recalled to Washington for “consultation”. He also stated that he “could scarcely believe that such things could occur in a twentieth-century civilization”.

Privately, Joseph Kennedy expressed his dismay as well, in a letter to Charles Lindbergh. Lindbergh had toured Nazi Germany several times, and even flown the Luftwaffe’s newest fighter airplane. Like Kennedy, he supported friendly relations between the United States and Germany. To the aviator Kennedy wrote in reference to Hitler’s government, “Isn’t there some way to persuade it is on a situation like this that the whole program of saving western civilization might hinge? It is more and more difficult for those seeking peaceful solutions to advocate any plan when the papers are filled with such horror”.

The Curious Relationship of Joseph Kennedy, Sr. and Franklin D. Roosevelt
Herbert von Dirksen, Chamberlain, and Ribbentrop in Germany, September, 1938. Bundesarchiv

17. The Germans considered Kennedy an ally in London

While Kennedy served as Ambassador, and before Germany declared war on Great Britain, he met several times with the German Ambassador to Great Britain, Herbert von Dirksen. Following the war, captured documents included letters written by von Dirksen to the State Secretary of the German Foreign Ministry, Ernst Freiherr von Weizsacker. Von Dirksen reported to his superior that Kennedy understood what he (von Dirksen) called “the Jewish question”. According to von Dirksen, the Ambassador was more concerned with the manner in which the Germans were dealing with the issue, which gained negative public attention.

Von Dirksen quoted Kennedy in one letter as having said, “The President was not anti-German, but desired friendly relations with Germany”. Kennedy reportedly told the German Ambassador that the president’s advisors and others who had visited Germany were “afraid of the Jews and did not dare say anything good about Germany” (referring to Jewish influence in the American press, government, and finance). Kennedy also told von Dirksen that public opinion in the United States was largely shaped by the east coast press, and “that it was strongly influenced by the Jews”.

The Curious Relationship of Joseph Kennedy, Sr. and Franklin D. Roosevelt
Prime Minister Chamberlain returned from Munich to announce “peace in our time” in 1938. Wikimedia

18. The Munich Pact widened the breach between Kennedy and Roosevelt

As the crisis over German annexation of the Sudetenland grew tense in September, 1938, Kennedy informed the British government that the American president, “had decided to go in with Chamberlain; whatever course Chamberlain desires to adopt he would think right”. The point under contention was whether Chamberlain should meet with Hitler in Munich and negotiate a settlement of the crisis. Roosevelt had not so decided to publicly endorse a negotiated settlement of the situation, which could (and did) result in the British and French conceding with Hitler’s demands, with American endorsement of the agreement.

Roosevelt was also communicating with Hitler during the crisis, including appeals for the negotiations to continue, in an effort to avoid war. His appeals were not answered by Hitler but the negotiations continued. Kennedy’s involvement in the Munich negotiations was separate from Roosevelt’s, for the most part, and was dominated by his relaying messages from the State Department. Roosevelt wanted it to appear the United States had not endorsed the swapping of European territory through a deal in which the country from which the territory was taken was not represented at the negotiations. Kennedy relayed to the British that the reality of the situation was that Roosevelt simply wanted to avoid war.

The Curious Relationship of Joseph Kennedy, Sr. and Franklin D. Roosevelt
The idea of approaching Herman Goering’s financial advisor with the promise of a loan in gold did not originate with Kennedy. Wikimedia

19. Kennedy attempted to negotiate a payment in gold to the Nazis

In May, 1939, Kennedy met with Helmut Wohlthat in London. Wohlthat was a highly placed Nazi official and the Chief Economic Advisor to Reichsmarshal Herman Goering, then the second highest ranking Nazi official in Germany, after Adolf Hitler. Kennedy had previously learned from James Mooney, General Motors Corporation chief overseas director, that during a meeting between Mooney and Wohlthat the latter had expressed Germany would be open to an arrangement through which trade between the United States, Germany, and Great Britain could be normalized. The arrangement was contingent upon a loan to Germany in gold.

Washington rejected the notion out of hand, but Kennedy, no doubt relying on his belief in his business and negotiating abilities, was intrigued. Though FDR had already rejected the plan, Kennedy arranged to meet with Wohlthat. They met secretly in London on May 9, and Wohlthat returned to Germany, undoubtedly conveying the results to Goering. As a result of the meeting, British agents began spying on Kennedy, concerned that he was a Nazi sympathizer and in league with German financiers. No further meetings were conducted concerning the loan of gold to the German government.

The Curious Relationship of Joseph Kennedy, Sr. and Franklin D. Roosevelt
Winston Churchill grew increasingly distrustful of Kennedy, and communicated directly with Roosevelt. Imperial War Museum

20. Kennedy became isolated when Great Britain declared war on Germany

On September 3, 1939, Great Britain declared war on Nazi Germany and Winston Churchill was appointed as First Lord of the Admiralty, a post he had held during World War I. Churchill began, with the knowledge of Chamberlain’s War Cabinet, a correspondence with FDR which eventually ran to over 2,000 letters and telegrams. The future Prime Minister had by then developed a profound distrust in the American Ambassador to Great Britain, Joseph Kennedy. Churchill considered Kennedy a Nazi sympathizer and anti-British. Kennedy began sending reports to the United States which expressed growing doubt in Britain’s ability to defeat the Germans.

In May, 1940, as the Germans swept into France and the Low Countries, the Chamberlain government fell and after negotiations between political factions designated Churchill as most likely to be able to form a government, King George VI asked him to do so. Churchill began a campaign to have Kennedy removed in response to the latter’s continued speeches and interviews which both discouraged excessive American aid to Britain and were pessimistic regarding Great Britain prevailing in the war. He was also negative about the British war effort in private correspondence, which grew considerably worse as the war shifted to the skies over Great Britain.

The Curious Relationship of Joseph Kennedy, Sr. and Franklin D. Roosevelt
Kennedy grew convinced that English resistance to the Germans was futile. Wikimedia

21. Kennedy remained in London during the early stages of the Battle of Britain and the Blitz

When the Germans began bombing British airfields, and later cities during the Battle of Britain, Kennedy sent back to his superiors in Washington increasingly pessimistic reports of the British resistance. At the same time, Roosevelt was receiving reports from special missions he dispatched to Britain, as well as from Churchill, which encouraged the president to provide aid to the British. In a letter to his son John, written in September, 1940 in London, Kennedy described the ease with which German bombers arrived from their bases in France, and hinted that they could increase the bombing at will. He hinted that only the belief in American aid was keeping Britain in the war.

The father also told the son that the British people were not being told the truth about the progress of the war. “There is no question but what they are covering up a great deal in the English press”, he wrote, adding that much was being censored entirely. “It is things like that which give me great doubts as to the complete reliability of the reports out of here”, he added. Kennedy acknowledged to his son that he didn’t think German reports were completely reliable either, and the same doubts expressed to his son in a private letter were readily apparent in his official reports and communications with the State Department.

The Curious Relationship of Joseph Kennedy, Sr. and Franklin D. Roosevelt
In Kennedy’s view, neither the British nor the American public were being told the truth about the war in Europe. Wikimedia

22. Kennedy believed the war in Europe was not about saving democracy

As the Battle of Britain raged, Ambassador Kennedy reiterated his views that the war being fought against the Germans and Italians was not about saving democracy. He believed it was about saving the British Empire and the existing world hegemony. In late 1940 Kennedy granted an interview to two reporters, Ralph Coglan (St. Louis Post-Dispatch) and Louis Lyons (Boston Globe). The interview covered a wide variety of subjects, including antisemitism. In it, Kennedy expressed a sense of urgency over the war and Britain’s ability to withstand the German onslaught, claiming it was essential for the United States to buy time.

“As long as she (Britain) is in there, we have time to prepare”, he was quoted as having said, stating that the crux of the issue was the ensuing six months. He added, “It isn’t that she’s fighting for democracy. That’s the bunk. She’s fighting for self-preservation, just as we will if it comes to us…” Kennedy also claimed that the American people were being misled regarding the causes and fighting of the war. “I know more about the European situation than anybody else, and it’s up to me to see that the country gets it”. When he then made the claim that democracy was dead in Britain, Roosevelt had had enough.

The Curious Relationship of Joseph Kennedy, Sr. and Franklin D. Roosevelt
By the fall of 1940 FDR was fed up with his Ambassador to Great Britain. Wikimedia

23. Kennedy was recalled and fired as Ambassador to Great Britain in November, 1940

When Roosevelt announced he was going to run for a third consecutive term as president, then unprecedented, Kennedy committed the unpardonable political sin of giving him an endorsement which was less than enthusiastic. The combination of gaffes was too much for Roosevelt to endure and though Kennedy was allowed to resign there was little question that FDR had fired him. Officially, Kennedy was said to be retired. Churchill was pleased, until Kennedy refused to go away quietly. In January, 1941 Kennedy gave a speech reported by the Associated Press in newspapers across the country, arguing against several aspects of the proposed Lend Lease bill before Congress.

Kennedy stated that he supported aid to Great Britain, but that it “should not and must not go to the point where war becomes inevitable”. Kennedy also stated that the lend-lease bill proposed by Roosevelt gave the president, “authority unheard of in our history”. The former Ambassador argued that America should rearm itself first. “The more we rearm, the larger our arsenal, the more we shall have available for England”. He also claimed that “The American people want to avoid war” and indicated that aid to Great Britain should be in the form of outright gifts, questioning the British ability to repay loans.

The Curious Relationship of Joseph Kennedy, Sr. and Franklin D. Roosevelt
FDR had no further use for Kennedy politically for the rest of his administration. Wikimedia

24. Kennedy’s political career ended with his resignation in 1940

Ambassador to the Court of St. James was the last political position held by Joseph Kennedy Sr. He did not completely fade from the political scene, in 1941 he testified during congressional hearings over lend-lease. Kennedy made clear that he favored aid to the British, but not at the expense of weakening America’s own defenses. He also argued against expanding the power of the presidency. When Roosevelt announced his intention of running for a fourth term Joe Kennedy Jr. refused to support the nomination.

In 1944 Kennedy and virtually everyone who knew Roosevelt could see that the president was but a shell of the man who had entered office in 1933, weak, infirm, and painfully thin. To nearly all, but kept from the American public, it was clear that the chances of Roosevelt surviving a fourth term were slim. Truman was shocked when he met with the president at his unhealthy appearance. Kennedy offered his services to the war effort in a variety of posts and though Roosevelt remained friendly on a personal level, there was no effort to solicit further service from the former ambassador. His money though was welcomed in numerous Democratic campaigns.

The Curious Relationship of Joseph Kennedy, Sr. and Franklin D. Roosevelt
Joe Kennedy and his family in Hyannisport in 1931, before the start of his political career. JFK Presidential Library

25. Joseph Kennedy Sr. remains a controversial and enigmatic figure today

Joseph Kennedy, like all members of the extended family of which he was the patriarch, is a highly controversial and polarizing figure today. He is often condemned as a criminal, a womanizer, an irresponsible father who had his daughter lobotomized and then institutionalized, and many other things. Some are true, some are exaggerated, and some are the smears of those who simply hate the name Kennedy. A search for truth that penetrates the veil of hatred and the myths it created reveals a far more complex portrait of the man. He was certainly no saint, but neither was he Satan in Irish disguise.

His personal papers remain in the care of the John F. Kennedy Presidential Library, where few have had unfettered access to them (biographer Doris Kearns Goodwin is one) and where they are likely to remain for the foreseeable future. The American Library of Congress contains much of his correspondence from his various government posts, as does the FDR Presidential Library, the State Department Archives, and the National Archives. The true story of the man is available for those willing to dispel preconceived notions and myths. It is far more interesting than the idea of Kennedy simply having been the man known as Bootlegger Joe.


Where do we find this stuff? Here are our sources:

“The Fitzgeralds and the Kennedys: An American Saga”. Doris Kearns Goodwin. 1987

“The Wedding That Changed American History”. James W. Graham, TIME Magazine. October 7, 2014

“The Biggest Kennedy Myth”. Daniel Okrent, Newsweek/Daily Beast. April 7, 2013

“Joseph Kennedy Presents His Hollywood Years”. Carl Beauchamp. 2009

“The Patriarch: The Remarkable Life and Turbulent Times of Joseph P. Kennedy”. 2012

“Franklin D. Roosevelt and the Third American Revolution”. Mario R. DiNunzio. 2011

“Affectionately, FDR”. James Roosevelt. 1959

“From Wall Street to Sing Sing”. Elliot Rosenberg, The Wall Street Journal. August 9, 2016

“The Press: The Colonel’s Century”. TIME Magazine. June 9, 1947. Online

“The Shipbuilding Program of the US Maritime Commission”. Article, MARAD. Online

“How Britain Hoped To Avoid War With Germany In The 1930s”. James Taylor, Imperial War Museum. Online

“Neville Chamberlain and Appeasement”. Article, The Guardian. September 5, 2009

“Joseph Kennedy and the Jews”. Edward Renehan, History News Network. Online

“November, 1938: FDR Day by Day”. FDR Presidential Library. Online

“Joseph P. Kennedy: Controversial Ambassador to Great Britain”. Peter Kross, Warfare History Network. Online

“The Secret of the Churchill-Roosevelt Correspondence: September 1939 – May 1940”. James Leutze, Journal of Contemporary History. July, 1975. Online

“Kennedy, Joseph P. Sr.: Letters from JFK”. Archives, JFK Presidential Library. Online

“The Kennedys: Is Democracy Finished?. Article, PBS.Org.

“Truman”. David McCullough. 1992