Statement of the Facts in the federal case against Robert Emmet O'Malley, Inmate #55296, by Maurice M. Milligan, U.S. Attorney. O'Malley pleaded guilty to charges of tax evasion, and this document summarizes the investigation and findings of the case against him. O'Malley was sentenced to one year and one day in the U.S.
O'Malley, R. Emmet
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When it comes to assessing the trajectory of a political machine such as the one cobbled together over time by first Jim Pendergast, and then by his younger brother “Boss” Tom Pendergast, it is always best to follow the advice of the later Watergate journalists – that is, to “follow the money.” Under Jim, the Pendergast machine seems to have dealt more in dispensing jobs and small favors, with Jim taking a rather small cut of the proceeds. Jim, however, could meet his relatively small personal needs, which included taking care of his bride Mary Doerr (married in 1886) and her young son by a previous marriage. He chose never to live “high on the hog.” Tom, on the other hand, always seemed to need more money, especially after his own marriage to Carolyn Elizabeth Dunn in 1910.