At the end of Franklin’s first year of law school, he and Eleanor embarked on an extended three-month honeymoon in Europe that took them through England, France, Italy, Switzerland, Germany, and then back through Scotland and England before returning home on the Kronprinz Wilhelm of the Norddeutscher-Lloyd Line. It was toward the end of that summer of 1905, when the couple arrived in Paris, that they consulted a famous clairvoyant, and Franklin reported to his mother that she had predicted that “E. is to inherit a fortune … and I am to be President of the U.S. or of the Equitable, I couldn’t make out which!” His jokey offhand comment suggests that even at this early stage he had probably already given some thoughts as to his future, although we can safely assume it did not have anything to do with the Equitable Life Insurance Company.
Throughout that summer, wherever the newlyweds traveled, the European papers were filled with praise for President Theodore Roosevelt, who had brought Russian and Japanese diplomats together in Portsmouth, New Hampshire, to negotiate an end to their bitter war. In a letter home to his mother, Franklin reported: “Everyone is talking about Cousin Theodore, saying that he is the most prominent figure of present day history, and adopting towards our country in general a most respectful and almost loving tone. What a change has come over English opinion in the last few years! Even the French were quite enthusiastic, but the German tone seemed to hide a certain animosity and jealousy as usual.”
As the time approached to return home, Franklin learned that he had failed two courses at Columbia—Contracts and Pleading & Practice—and would have to make them up before he would be allowed to start his second year. He was unperturbed. A hurried cable home brought the required textbooks by the next boat, and he spent most of the return crossing swotting up on the failed courses in preparation for the makeup tests, both of which he passed easily soon after returning to New York, in plenty of time before the start of his second year of study. It was another example of just how formidable his intellect could be when he chose to use it.
The following June, while he still had one more year to go in law school, FDR took the eight-hour examination for admission to the New York Bar. Eight months later, in February 1907, he received word that he had passed with flying colors, and he immediately informed Columbia that he would not return for the spring term. A law degree held no interest. The license to practice was enough for him.
Now all he needed was a job; and for someone from such a prominent family, the choice of where to look for one was not overly difficult. He applied to Carter, Ledyard & Milburn, of 54 Wall Street, one of the city’s most prestigious law firms, and in due course he received a letter from one of the partners, Edmund L. Baylies, offering him a position. “I have talked over with Mr. Ledyard the question of your coming to our office,” he wrote, “and I find that we can arrange to have a place for you at such time as you may wish to come here in the autumn, not later than October 1st, preferably a week or so earlier.
“In case you come to us, the arrangement will be the same as we usually make in such cases, that is to say, you will come to us the first year without salary, and after you have been with us for a year we would expect, if you remain, to pay you a salary which, however, at the outset would necessarily be rather small.”
Many years later, during a presidential press conference in 1941, Roosevelt remembered his early days at Carter, Ledyard & Milburn. “Somebody … said ‘Go up and answer the calendar call in the Supreme Court tomorrow morning.… We have such and such a case on.’ I had never been in a court of law in my life.… Then the next day somebody gave me a deed of transfer of some land. He said, ‘Take it up to the County Clerk’s office.’ I had never been in a county clerk’s office. And there I was, theoretically a full-fledged lawyer!”
For the rest of the time, when he wasn’t running errands, he sat behind a high roll-top desk, handling petty cases brought against the firm’s major clients, including American Express and John D. Rockefeller’s Standard Oil. It probably amused him that he was working on behalf of the same powerful “malefactors of great wealth” that President Theodore Roosevelt was so determined to bring down.
But with every passing day it was becoming increasingly clear to him that he was, in his own words, little more than “a full time office boy.” For someone as restless and determined as Franklin Roosevelt, the pressure must have been growing to find some meaningful direction to his life, some plan of action that would feed his ambitions and take him away from the world of law, which he found so confining.
Somewhere toward the end of that first year on Wall Street, on a particularly slow day at the office, FDR and his five fellow law clerks sat at their desks casually discussing their hopes and plans for the future. When it came his turn, Franklin surprised his listeners by stating clearly that a life in the law was not for him. He would, when the opportunity presented itself, go into politics and run for the New York State Legislature. After an indeterminate stay in Albany he would, he said with no hint of irony, somehow arrange to get himself appointed assistant secretary of the Navy in Washington. From there he would run for Governor of New York, and “anyone who is Governor of New York,” he explained in reasoned tones, “has a good chance to be president with any luck.”
Of course, it was not lost on any of his listeners that FDR was precisely retracing the meteoric rise of Theodore Roosevelt, and the fact that the speaker carried the same name gave his prediction a certain semblance of plausibility. The most significant reaction on the part of his fellow law clerks to his amazing pronouncement was neither laughter nor derisive hooting. Instead, they heard him out quietly, apparently accepting at face value his confession of almost unparalleled hubris. Grenville Clark, one of the other law clerks that day, recalled the scene years later, remembering that Roosevelt spoke modestly enough, and with such sincerity as to convince them all that his outlined future sounded “entirely reasonable.”
Even today, when we know that FDR’s career path eventually fulfilled his casual daydream to the letter, one item in his litany of offices stands out in bold relief—his plan to be named assistant secretary of the Navy. Apparently not just any subcabinet office would do, only the job that TR had once held. And how was he going to manage that? It was not an office he could campaign for, in the normal sense. Someone—a president!—would have to appoint him, a difficult thing to arrange, at best. His listeners did not challenge him on the point, and it is likely that he set the question aside to be dealt with at a more appropriate time.