It’s likely that when Darrow met Mary Field, he was searching for respite from the tension entailed in all that he had committed himself to upon returning to Chicago following the ordeal of the “Big Bill Haywood” trial in Idaho. He was bound to his “irksome law work” but also to his marriage. After his illness in Idaho and hospitalization in Los Angeles, Clarence understood well that Ruby was indispensable in making possible everything that he did in his professional life. Nonetheless, he remained bitterly disappointed at having to postpone indefinitely his hopes of becoming a full-time public intellectual, and somehow, he blamed Ruby. So, Clarence sought solace in the arms of a woman 21 years his junior, who had captivated him with her witty and mischievous demeanor. Yet they both knew that nothing permanent could ever come of their relationship. As it was recounted years later by Mary’s daughter, “The sex part was evidently short-lived and the relationship settled into a deep friendship.” Their friendship was kept alive by letters; Ruby knew nothing of these contacts.
Within months of their meeting, Mary left her position as a social worker, and before the end of 1909 she was off to New York City. There, on Darrow’s recommendation, she began work as a reporter with a newspaper sympathetic to organized labor. As confirmed by Darrow’s correspondence to Mary, there are adulterers who should never write letters to their paramours. This maxim is doubly true when it’s an older man writing to a young woman. In one of Darrow’s many letters to Mary he wrote, “I miss you all the time. No one else is so bright & clever & sympathetic to say nothing of sweet and dear & I wonder how you are & what you are doing in the big city…Am tired & hungry & wish you were here to eat & drink with me & talk to me with your low, sweet kind sympathetic voice. I will send you some money tomorrow.” Like so many furtive lovers, Darrow had no restraint once he took pen to hand, writing words that he never would have spoken in the presence of a third person.
At about the time Darrow began to despair over the lack of facts to support a defense for the McNamara Brothers, he learned that Mary was on her way to Los Angeles. When Darrow first heard of her plans, he discouraged her, but Bridgeman’s Magazine, official publication of the Iron Workers Union, had hired her to cover the trial and Mary needed the work. The trial was shaping up to be a major story and she couldn’t resist it. The anguish, strife and humiliation which are an inevitable part of a love triangle were on their way to Ruby.
Why did Darrow permit this triangle to play out? Larger than life personalities have bigger than normal egos. A woman twenty-one years his junior finding him attractive inflated his ego as nothing else could. Yet it’s not possible that Darrow shared with Mary Field the bond that existed between him and Ruby, nor the extent to which his ability to function proficiently as an attorney was dependent upon her. Mary was a sexual frolic that evolved into a relationship grounded in her willingness to be a sounding board for all of Darrow’s courtroom triumphs, social critiques, and personal tribulations; their relationship never had an aura of permanency.
As for Mary’s interactions with Ruby, the more they learned about one another, the greater their mutual contempt. “Ruby thought Molly an impetuous, self-centered sycophant. Molly thought Ruby insane, mean and uncouth.” Over the next 18 months, they were forced into one another’s company; it had to have been disturbing for both.
Piecing together the available information, what emerges is that Darrow’s relationship with Mary Field was much like the familiar scenario of dalliances by other celebrated older men with younger women. Benjamin Franklin illustrates this phenomenon well. Darrow and Franklin were both flirtatious, highly intelligent and had a droll sense of humor. Each loved the sound of his own voice and never hesitated to prattle on at length, as long as he had an audience, even an audience of one. They likewise relished receiving letters from, and writing to, young female devotees. Combine those traits with their celebrity status, and almost any young, educated woman of their time would have been flattered to have received their attention. In turn, both Franklin and Darrow reveled in being fussed over by young women and enjoyed flirting with them. But alas, neither seems to have been a genuine lady-killer once into his fifties. By that point in their lives, they were far more capable of memorable conversation than noteworthy fornication.