From the time I was able to think of such things, I have been obsessed—yes, I admit it—with two words: What if. It began when, as a boy, I wondered, “What if I had a different mother and father?” I had read in one of my mother’s magazines that the beautiful movie actress Myrna Loy and President Roosevelt were in love with each other, and I dreamed of what it might be like if they were my parents. How my life would be different and better. How I would be living in the White House, with plenty of heat in the winter and hot water when I showered. I would get to know my favorite actors and actresses and meet generals like McArthur and Eisenhower and eat off the same plates that Lincoln ate off.
As I grew older, my obsession with “what if” changed. It was no longer a fantasy, looking forward, but a philosophical musing, looking back. For example, what if I’d never had that Prep experience with that sick priest? I would likely have gone on to a Catholic college on a scholarship and not had the John Adams high school experience, which helped to heal me and restored my faith in myself—and which has had a positive effect on me to this day. Just as significantly, if I had not gone to John Adams, I would never have met Joan, my wife of seventy years, and would never have had our children—Alison, Lynn, Nancy, and Peter. I would not have been a messenger boy for a notorious banana company or moved to Boston. I would not have had the friends I made. My Prep experience led to my life.
Another way of describing what-ifs is to call them “turning points.” They are the choices you make. The accidents that happen. But also, what doesn’t happen. I think about all the near misses; what if those close calls had never occurred? That to me is the scary part. How much would I have missed? Our lives are shaped by chance, destiny, and the actions of others.
I often think of something my mother did when I was thirteen. She sat me down and told me I had not gotten into Regis High School in Manhattan. It was where I should have gone. It was where I really wanted to go. There would have been no tuition and no sadistic Father Hess. There would have been plenty of scholarship money to help a smart kid like me go on to a good Catholic college. I would not have been a charity case. I knew I had done well on the admission test and in my interview. I couldn’t understand why I had been rejected. Forty years later, my mother told me that I had been admitted, but she had felt I should go to Prep. She had lied to me. What a terrible thing for a mother to do! And yet it led to my life and so many good things. Even the bad actions of others can have a good result.
What-ifs can change the course of history. John F. Kennedy would not have been elected to the Senate and gone on to become president, for example, had it not been for the action of a man named Lloyd Waring. Very little has been written about Waring. As far as I know, nobody alive knows about his role in helping Kennedy win his Senate seat in 1954, a win that paved the way for his victory over Richard Nixon in the 1960 presidential election.
I know this story because Lloyd himself told it to me toward the end of his long life. But first, a bit about him.
He was born in Melrose, Massachusetts, in 1902. His father died when he was in his early teens, and as the eldest, he was expected to care for his brothers, sisters, and mother. I don’t think he ever finished high school, and he certainly never went to college. He had to make money. At age seventeen, he applied for job at Kidder, Peabody, a Massachusetts firm of investment bankers, stock and bond brokers, and traders. Lloyd was good at math and had a keen interest in finance, but with no education, no connections, and no experience, the only role open to him was as a messenger. Even at that low level he was required to see a company doctor and submit to a physical. The examination determined that Lloyd had tuberculosis and would likely not live past the age of twenty-one. He was rejected.
Lloyd told me he had begged for the job and agreed to resign as soon as his health began to deteriorate. He even agreed to put that promise in writing. He was eighty when he told me this story. He lived to be ninety-five and swam in the Atlantic Ocean twelve months a year until he reached ninety. He did not have TB.
Yet his promise to resign had worked, and he was hired at Kidder, Peabody. After a few months somebody realized that he was capable of much more than being a messenger, and he was given a low-level desk job. From there he rose quickly. He became an analyst and was then given a couple of small accounts to manage. Those small accounts grew larger. Customers began to ask for Lloyd as word of mouth of his expertise spread. But the executives at Kidder were all Brahmins and Harvard men. Lloyd was from the wrong side of the tracks. He didn’t speak like them, dress like them, or think like them. Yet he continued to advance in responsibility and salary, and in 1938, at the age of thirty-six, he became president of the Boston Security Traders Association—the youngest in its history. Fifteen years later, he became a partner. He was a superstar not only at Kidder but in the industry.
At that time, everyone who worked at Kidder, Peabody, without exception, was Republican. That was my experience. Most Boston companies and Boston social clubs were. That suited Lloyd’s conservative views, and he joined the party and became very active in Massachusetts Republican politics. He was very skilled at raising money and did not mind knocking on doors to ask strangers for their votes and their money to help Republican candidates. ln those days, Republicans did a lot better in Massachusetts elections than they do now. And Lloyd rose rapidly in the party. He was never interested in public office for himself—only in advancing the Republican agenda.
Yet Lloyd knew that the movers and shakers in the party, especially those running for public office, never really accepted him or his advice. They valued only his ability to raise money. Some were better at hiding their feelings than others. One who never tried to hide his feelings about Lloyd was Henry Cabot Lodge, Jr., who represented Massachusetts in the US Senate. They were precisely the same age. Lloyd said that Lodge “ritzed me every chance he got.” To “ritz” someone was a common term at the time. It meant to treat someone as an inferior—intellectually, socially, economically, and in every other way. A person who ritzes feels and acts superior and doesn’t care if the one they are ritzing knows it.
In the late forties, Lloyd served as chairman of the Massachusetts Republican Party, and in the early fifties he was the party’s finance chairman. He was treasurer of both Eisenhower presidential campaigns and, later, the New England director of Barry Goldwater’s presidential campaign. (Lloyd loved Goldwater.) He also raised funds for Richard Nixon’s campaigns and was four times a delegate to Republican national conventions. He had a lot of clout in the Republican Party, and his sympathies were entirely Republican.
ln 1952, Henry Cabot Lodge was in a tight race for reelection against Kennedy, then a congressman from working-class Charlestown. Lodge needed all the support he could get—he especially needed Republican party funding for the ads, leaflets, signs, and other means of getting his name into the heads of Massachusetts voters. Of course, Lloyd held the purse strings. And Lodge had ritzed Lloyd once too often. Lloyd told me that around that time there had been an incident between him and Lodge. He didn’t tell me what it was, only that Lodge ritzed him “for the last time.” He decided to get back at Lodge by using his influence to withhold some funds. At the crucial point in the campaign, Lodge lacked the money to match what Kennedy was spending—and JFK was well-funded, thanks to his father and other sources from within the Democratic party.
The result, as everyone knows, was that Lodge was defeated by Kennedy, who secured 51.5 percent of the vote. Joe Kennedy was elated. At long last, an Irish Catholic Democrat had humbled a scion of the WASP Boston elite. For Joe, this victory was the most satisfying of all his family’s electoral triumphs. And it paved the way for JFK’s 1960 presidential campaign. If Lodge he had won the Senate election, Kennedy would never have run for the presidency in 1960. The United States would never have had that young energetic, optimistic man in the White House. There would have been no tragic assassination with all its consequences for the years to come. There would have been no Lyndon Johnson presidency, and who knows what other impact.
Lloyd told me that story more than fifty years after the 1952 race, adding that it was the only time he ever helped a Democrat. As he spoke, I could see a flush on his face. After all those years, he still remembered how Lodge had treated him. The Lodge campaign had claimed at the time that the loss was due to Lodge’s efforts to help Eisenhower win the Republican nomination, thereby neglecting his own campaign. But Lloyd knew better. “Lodge fought like the devil to win,” he told me, “but it was me who helped him to lose that election, and I am proud of it. The fact is Kennedy was the better candidate.” He went out of his way to list the Republican candidates he had helped to win over the years, including Eisenhower, Nixon, Ford, Reagan, and both Bushes. There were pictures of Lloyd and all the presidents he helped get elected on the walls of his house.
That’s the story. Is it true? I certainly believe it. I know how it feels to be looked down upon. Even after half a century. And I love how the story illustrates so well how one man’s what-if can shape world history.
I count myself lucky to have known Lloyd. He and I had oceanfront houses in Rockport, and when I would arrive at mine for the weekend, there would almost always be a message on my answering machine asking me to come over on Saturday or Sunday to pitch horseshoes (a Republican game he was very good at) and have a bowl of chowder. I enjoyed our visits. I liked him. But I would never have wanted to work for him. He could be tough. And stubborn.
Lloyd had an office in Gloucester with a direct line to the Kidder, Peabody office in Boston. He made daily trades involving several portfolios he managed, and he also used the office to run the affairs of the Amelia Peabody Foundation. Miss Peabody was the sole surviving heir of Frank Everett Peabody, an early partner in the brokerage house, and Lloyd handled her financial affairs until her death in 1984. She was one high-born Brahmin who never looked down on Lloyd.
After she died, he continued to run her foundation, worth, I believe, over $100 million. James St. Clair, a partner at the Yankee law firm Hale and Dorr in Boston, played a large and lucrative role in the foundation all his life.
Lloyd recommended St. Clair to Nixon during the Watergate crisis, and it was St. Clair who finally convinced Nixon to resign. I believe St. Clair also came up with the presidential pardon plan shortly after the resignation, but I have no proof of that.
St. Clair so valued his association with Lloyd that he came up to Rockport every month and stayed for dinner. On one such night in the eighties, I asked St. Clair if he had seen my docudrama, White House Transcripts. He said he had and made no further comment. Then I asked him if President Nixon had seen it. He said, “No comment—I never discuss my clients.” Lastly, I asked was if he intended to write a book about his involvement in Nixon’s final days—one of the greatest what-if stories in American history. His response? “I’m not the kind of a lawyer who writes books.”
St. Clair had no desire to tell his story, but Lloyd’s stories had helped me understand how life worked. On at least one occasion I returned the favor. One Saturday afternoon, as I was leaving Lloyd’s house, he asked me to drop an envelope off at the post office. He told me it contained an alimony payment and muttered something about how angry it made him to have to write that check each month. It really bothered him.
I knew him well enough by then to say, “Lloyd, get over it. It is only money, and you are a very rich man. You were miserable when you were married to that woman, and now you’re happily married. You solved the problem with money. And there are so many problems that can’t be solved with all the money in the world. Like a terminal illness. So be grateful that you write that check each month.”
He looked at me for a minute, then asked me to repeat what I just said. I did. He said, “You are right, my boy. I feel so much better.”
After that day, he called me many times, asking me to repeat what I had told him about solving problems with money. Once he said he was having trouble remembering it, and he thought it should be written and hung on a wall. Well, I was happy to help him out in that small way. Happy to help him understand his own what-if.