to undergo. “No one is able to figure out what’s wrong with me. They give me enemas until it comes out like drinking water which they all take a sip of. Then surrounded by nurses the doctor first stuck his finger up my ass. I just blushed because you know how it is. He wiggled suggestively and I rolled ’em in the aisles by saying ‘you have good motion’!”
When Jack returns to Choate in winter 1935, his mischievous streak erupts. “What makes the whole problem more difficult,” says the Choate housemaster Earl Leinbach, who has to contend with nuisances such as pillows bursting from dorm rooms, “is Jack’s winning smile and charming personality.” (Years later, in 1942, his eventual bride Jackie’s own gifts as a mimic also land her in trouble at the exclusive Holton-Arms School in Washington, DC, when she is caught mid-parody by the teacher she is mocking, though nothing on the level of mayhem that Jack and Lem wreak with “the Muckers,” their secret society of pranksters.)
But when Jack goes too far and sets off contraband firecrackers in the bathroom, destroying a toilet seat, he faces expulsion. Headmaster George St. John fumes, “I couldn’t see how two boys from the same family as were Joe and Jack could be so different.”
Joe Sr. is called to St. John’s office, saving Jack from expulsion, but not from judgment. “Don’t let me lose confidence in you again,” he writes in a letter following the incident, “because it will be a nearly impossible task to restore it.”
Jack graduates sixty-fifth in a class of 110. And he pulls off one last prank, persuading classmates to trade votes so that he’s named “Most Likely to Succeed”—in a rigged election.
Chapter 11
In 1934, Jack Kennedy and Lem Billings, both seventeen years old, dress in formalwear for a night in Harlem, New York City. They tell their cabdriver to bypass the famous Cotton Club where the great Cab Calloway performs. On this night, the boys have in mind only one experience they want to enjoy: losing their virginity.
Ralph Horton, another school friend, escorts them to a brothel. First, they watch a pornographic movie for a pricey three dollars. Then Jack accompanies a prostitute into a room, where the deed is quickly done.
“They were frightened to death they’d get VD,” says Horton. “So, I went with them to the hospital…where they got these salves and creams and a thing to shove up their penis to clean it out.”
Sex is always on Jack’s mind. Throughout his life, Jack will follow the Kennedy male tradition of coming on to any attractive woman—and succeeding. “Every woman either wants to mother him or marry him,” the New York Times columnist James Reston would write of Jack as a presidential candidate.
Attendance at Harvard is another rite of passage for Kennedy men. Joe Sr. is class of 1912; Joe Jr. graduates cum laude in the class of 1938, and Jack joins the class of 1940. Younger brothers Bobby and Ted will follow.
In college, Jack earns the same middling grades as he did at Choate. “He could do what he wanted,” the Harvard Crimson reports one of his professors as saying, “but he did not waste time on what did not interest him.”
Instead, he pursues athletics, excelling at swimming, tennis, and football. Even though the six-footer is underweight at 156 pounds, he’s a standout end for the freshman and junior varsity football teams, playing through the pain of a serious spinal injury he sustains in a game during his sophomore season.
Jack is a junior when FDR names his father ambassador to Great Britain in 1938. Though he remains at Harvard, he visits his expat family often during school breaks—he’s even there in Britain when they declare war on Germany on September 3, 1939.
That same day, the German submarine U-30 commits a war crime—torpedoing the SS Athenia, an unarmed transatlantic passenger liner bound for Canada, killing more than a hundred of the nearly fourteen hundred on board, including twenty-eight Americans.
Jack travels to Scotland as an impromptu junior ambassador to visit with American survivors of the sunken ship.
“Young John Kennedy came up from London and assured us that we were all the nearest things to the [American] nation’s heart and would be looked after,” Mildred Finley, a teacher who boarded a lifeboat and then a British destroyer on her way to safety in Glasgow, tells Scotland’s Daily Record.
“I, and several other of the most battered-looking survivors and children had pictures taken with him.”