The President’s Best Friend


Good-natured about Kennedy’s absentmindedness, Billings was humorously competitive about Kennedy’s popularity with girls. They each had a more or less steady girl friend throughout college: Billings dated Katharine Duncan Hartwell, a striking brunette from Stamford, Connecticut; Kennedy dated Olive Field Cawley. And both were successful with casual party dates, though Jack was the more sought after of the two. Lem constantly needled Jack about his success with girls, insisting it could only be attributed to his father’s wealth and fame. Kennedy disputed this theory, and ultimately decided to put it to the test. They agreed to switch names for one night. Ralph Horton arranged blind dates for them. Jack became LeMoyne Billings and turned over his father’s chauffeur-driven Rolls-Royce to Lem, who was introduced to his date as John F. Kennedy. The matter was settled to Jack’s satisfaction, Lem’s chagrin. “LeMoyne Billings” enjoyed a memorable date that night, “John Kennedy” had only a fair evening with his girl.


Increasingly their attention was drawn to the news from Europe. Nazi Berlin and Fascist Rome proclaimed a political Axis that year, Ethiopia fell to Mussolini, and the demilitarized zone of the Rhineland was suddenly occupied by the Nazi Führer. Germany and Italy both aided Franco’s forces in Spain’s Civil War. In May 1937 a short item appeared in a Pittsburgh newspaper: “Though all American passports legibly state, ‘Not good in Spain,’ ex-Pittsburgher K. LeMoyne Billings, son of Mrs. Frederic T. Billings who moved to Baltimore last year, and John Kennedy, son of Joseph P. Kennedy of Washington, will visit that war-torn country this summer for three weeks. They sail June 30 on the George Washington , will attempt to study war conditions.”

EUROPE, 1937

LEM AND JACK were on their own. The two-month grand tour began in Le Havre when Jack’s convertible Ford sedan was hauled off the boat. Kennedy had hopes of getting to Paris quickly, but before reaching the capital, Billings insisted on visiting every single cathedral town, from Rouen to Beauvais to the bomb-blasted ruins of Rheims. Billings had taken his first architecture course at Princeton and was now reaching a high pitch of excitement over the actual choir vaults and naves themselves. Usually a rapid motorist, Kennedy had to be content driving at cathedral pace while listening to Billings’s commentary on Gothic architecture.


Meanwhile, Jack’s traveling techniques got Lem involved in political discussions, nightlife, and events that were closed to the average tourist. Discovering a huge crowd swarming around Notre Dame in Paris, Jack led the way past police barricades and discovered that Cardinal Pacelli, the secretary of state of the Vatican (later Pope Pius XII), was celebrating Mass for the president of the Republic and numerous foreign dignitaries. Special passes were required, but Kennedy, with Billings in tow, marched straight up to the VIP portal and entered the cathedral without offering so much as a single word of his atrocious French. Billings was stopped, then pushed back into the crowd despite his protests in slightly less atrocious French.

At the Spanish border heavily armed guards turned them back. They stayed instead at nearby Saint-Jean-de-Luz with Kennedy’s Harvard classmate Alex de Portalis, whose family had a house on the Gulf of Gascogne.

Visiting Lourdes, Billings got sick. Next stop, Carcassonne, of which Kennedy remarked in his diary: “An old medieval town in perfect condition—which is more than can be said for Billings.” Despite Kennedy’s small winnings at the tables in Monte Carlo, they continued to stay in the cheapest hotels in deference to Billings’s budget. In Italy they attended a Mussolini rally, and Billings did impersonations of the Duce as they drove up to Germany.