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      Inferno

      The day Robert Ryan turned nine, the entire nation celebrated. All weekend long had come word that the Armistice was about to be signed, bringing home a million American soldiers from the trenches of France. In Chicago, where the boy lived, whistles began to sound and guns to go off in the predawn darkness of Monday, November 11, 1918. Women ran from their homes with overcoats tossed over their nightgowns, beating on pots and pans. The elevated trains coming from the Loop tied down their whistles and went screaming through the neighborhoods, confirming that the nation was at peace. People who ventured downtown for work were sent home by their employers, and by noon the neighborhood parties were rolling.¹ In Uptown, on the city’s North Side, young Bob ran around telling people this was his birthday and returned home with a few dollars in change. His parents, Tim and Mabel, made him give back most of the money, but even so this was a great day. Everyone had called this “the war to end war” — if that were true, then he would never have to die in a trench.

      The Ryans had no need for their neighbors’ charity; they were respectable, middle-class people who had worked their way up. Bob’s great-grandparents, Lawrence and Ellen Fitzpatrick Ryan, had immigrated from County Tipperary, Ireland, in 1852 during the Great Famine and settled in Pittsburgh, where times were tough (their son John would later tell Bob about the “No Irish Need Apply” signs that greeted them on their arrival). The family moved to Chicago four years later and eventually retreated about thirty miles south to the heavily Irish Catholic river town of Lockport, Illinois, along the Illinois and Michigan Canal.

      John and his older brother, Timothy E. Ryan, worked together as boat builders in the 1860s, then went their separate ways as John established his own business in town and Timothy (known as “T. E.”) returned to Chicago to try his hand at real estate speculation. John served as superintendent of the canal at one point and, with his wife, Johanna, raised a family of eight children. He liked his glass. “Although my grandfather drank a quart of whiskey a day for sixty-five years, he was never drunk or out of control,”² Bob later recorded in a memoir for his children.

      Up in Chicago, T. E. Ryan prospered, cofounding the real estate firm of Ryan and Walsh and building his family a mansion on Macalister Place on the Near West Side. He also established himself as a political brawler in the city’s well-oiled Democratic machine. Through the 1890s he won five terms as West Side assessor, and from 1902 to 1906 he served as Democratic committeeman for the Nineteenth Ward. T. E. was widely regarded as boss of the West Side, so popular and influential that, during the World’s Columbian Exposition in 1893, he was named grand marshal of the Irish Day parade. A portrait reproduced in an 1899 guidebook to state politics shows a handsome man with swept-back hair, a handlebar mustache, and a hungry glint in his eye. “One of the most popular men on the West Side,” the guidebook reported, “and a politician whose power is as strong as ever.”³ His success exerted an irresistible pull on John’s sons, and one by one they all drifted to Chicago.

      Timothy Aloysius Ryan was the second of John’s children, born in 1875, and in the 1890s he headed north to board with his illustrious uncle and get into business in the city. Tim proved to be an eager political protégé: in 1899 he was appointed chief clerk in the city attorney’s office, and five years later he ran for the state board of equalization in the Eighth Congressional District, billing himself as “T. A.” Ryan. His uncle bankrolled all this, apparently seeing in his tall and handsome young nephew a rising political star. Tim got himself started in the construction business and ran an unsuccessful campaign for West Town assessor, his uncle’s former position. “Father’s duties have always been somewhat vague in everyone’s mind,” Bob wrote. “In his twenties he seems to have been occupied principally with fancy vests, horse racing, attending prizefights, and a great deal of social drinking. In short, a rather well-known and well-liked man about town.”⁴

      By 1907, Chicago was home to five of John and Johanna’s sons. They were big men — one of Bob’s uncles stood six feet eight inches tall — with ambitions to match. Larry, Tim’s younger brother by eight years, had come north to clerk for T. E.’s real estate firm, and Tom, Joe, and John Jr. wanted to start their own construction firm so they might capitalize on their uncle’s political influence. But the brothers’ relationship with their uncle ruptured. According to Bob, Larry’s job “involved handling some funds and he was ultimately accused by his uncle of a minor embezzlement. Larry was about as liable to have done this as to burn down the Holy Name Cathedral. Father sided with his brother and left his uncle’s bed, board, and generous patronage for good.”⁵ From T. E.’s power base in the west, Tim and Larry relocated to the relatively unpopulated North Side, where they banded together with their siblings to turn the newly christened Ryan Company into a going concern.