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of dread before his wedding, though nothing as overwhelming as what Teddy was feeling. Jack should have understood what Teddy was experiencing. Jack knew that Teddy was not the vibrant, carefree young man he appeared to be. “Teddy, who has all the physical apparatus of being rather easygoing, a rancher or something, you know really taking life easy, he got an ulcer for a while there last year because he didn’t know if he was going to be able to stay in law school, because he’s not terribly quick,” Jack told Burns in 1959. For Jack, the ranch was his metaphor for freedom, for that road he had not taken. Jack did not seem to grasp that it was not just his studies that troubled his little brother but his impending wedding. Or more likely Jack chose not to tell his biographer that unpalatable truth.

Teddy was always doing whatever his father wanted him to do, and in marrying Joan he would be doing it again. “He stayed in and has done pretty well,” Jack continued, “but that demonstrates that’s really induced by outside pressures, because he’s most physically well-balanced and healthy but I mean it’s gotten to him now so he’s doomed to this treadmill too.” Teddy would be getting on the same arduous road that Jack was traveling now, and as his big brother saw it, there was no room to turn around and head back. Teddy’s anguish, then, was not a trivial matter. This marriage would put an end to most of whatever secret dreams Teddy had for a life in a wild, untamed world far beyond the family compound.

During the last week before the wedding Teddy went out drinking with his friends in New York nightclubs. He had a trust in the world beyond his family that his brothers no longer had. He talked to his friends about his doubts, and they shook their heads and said that there was nothing he could do. On the evening before the ceremony, when all should have been joy and anticipation, he took a close old friend aside and said that he feared he was making a dreadful mistake.

On that late November 1958 night, a great storm fell on Bronxville. Frigid winds blew at near-cyclone force, felling trees that had stood for decades, shattering windows, knocking down power lines, leaving much of the town in darkness. Even such a merciless act of nature as this was not going to postpone the wedding. In the morning the guests arrived, driving warily through streets littered with downed trees, flooded gutters, and broken glass. Bracing themselves against the frigid winds, they ran into the church.

As the last arrivals hurried into the vestibule, they were startled by a brilliant burst of light. One of the wedding gifts was a professional film of the wedding, and the church was lit up with floodlights like a Hollywood set. All of the participants wore hidden microphones. Jack was Teddy’s best man. As the two brothers stood behind the altar waiting for the ceremony to begin, Jack could see the anxiety on his baby brother’s face. Teddy was about to take vows of fidelity. Jack told him that he would still be able to do what he pleased when he got married. Jack was the best example of that. Teddy could have whatever women he wanted and live much as he had as a bachelor. These were unseemly words of advice for a wedding day, but they were an attempt to bolster Teddy and to prepare him for all the obligations that he would face as a Kennedy man. For Jack, sex was a residue of freedom outside his world of obligations and ambitions and he was telling Teddy that he could have that freedom too.

After the ceremony Teddy and Joan flew to Nassau. On the third night of their four-day honeymoon, Beaverbrook decided that his houseguests needed a romantic interlude by themselves. A boat took the couple to an isolated island where they could spend twenty-four hours by themselves. “We were dumped there for an overnight,” Joan recalled. “It was the worst experience of our life. It was a little cottage, practically a shack, on this tiny island, just sand. We slept on these mats. There were bugs, and it was a nightmare.”

When the newlyweds returned from their honeymoon,