pleased that his son would be schooled in the Catholic faith, though Mabel valued Loyola more for its academic reputation. The priests were known as stern taskmasters, and the curriculum was tough — along with the arts and sciences, the boys learned Latin, Greek, and Christian doctrine. Later in life, when Bob Ryan’s interests had turned to education, he would take a more skeptical view of Jesuit schooling. “The fathers were well-seasoned men who had a good deal of authority that they seldom used,” he remembered. “Huge areas of a fruitful life were almost ignored. Jesuit education was books and drill and writing and some discussion.”14
At the new school Bob began to distinguish himself in athletics, especially after a growth spurt propelled him to a height of six-foot-three, only an inch shorter than his father. He played football all four years and competed in track and field. Formidably big and agile on the gridiron, he was an All-City tackle his senior year. In school he struggled with Latin and especially chemistry but excelled in English, joining the literary society and working on the school magazine, The Prep. He read voraciously. “Truly, I may say that a man’s best friends are his books,” he wrote in the magazine his junior year. “Your companions may desert you, but your books will remain with you always and will never cease to be that source of enjoyment that they were when you first received them.”15
Ryan with his parents, Mabel and Tim. “You cannot know the difficulties that attend an only child,” he later wrote. “It is a feeling of being watched that lingers throughout life.” Robert Ryan Family
The book that changed his life was Hamlet, which he spent an entire semester studying under the instruction of his beloved English teacher, Father Joseph P. Conroy. The priest led the boys through the Elizabethan verse into the dark heart of the play, the young prince charged by the ghost of his dead father to avenge the treachery of his uncle, Claudius, and the unfaithfulness of his mother, Gertrude. Hamlet was full of moral conundrums, the hero torn between his conscience and his thirst for revenge. Bob was captivated: such rich language, such profound thoughts, such high drama. By the end of the semester he could recite practically the entire text. He fell in love with theater, reading Shakespeare, Chekhov, Shaw, and O’Neill, a writer who spoke to his own Irish melancholy. Their work awakened in him a hunger for self-expression, and he wondered if, instead of following his father into construction, he might become a playwright himself.
The money kept rolling in at the Ryan Company, and before long the family bought a Cadillac, then a Pierce-Arrow with a chauffeur to drive Tim to work. Bob got his own Ford and tooled around in bell-bottom suits and a fur coat. Tim became a patron of the Chicago Opera Association; he took Mabel to New York City to see all the shows. (Bob shared their love of musical theater; among his favorite performers were Fanny Brice and the great Irish-American showman George M. Cohan.) Tim Ryan, Bob wrote in a letter to his own children, “was always generous and kind to me — in a day when father-son relationships were not thought of as they are now.” His father was “a big man (6′ 4″ — 250 lbs.) with a radiant personality and strong sense of humor, and was idolized by many people. His other side was only displayed at home and was very hard to take.”
Bob wouldn’t elaborate on this statement, but he would note his father’s ambivalence toward the construction business, which hardly inspired one to join him. “Dad, I think, would have been content to have enough money to live well, eat well, play bridge, and tell stories to his rather small circle of friends.”16 Friction between father and son began to build as Bob’s graduation from Loyola drew near. Tim had mapped out his son’s future: he would stay at home, earn a professional degree at Loyola or DePaul or the University of Chicago, and find a good living for himself as the next generation of the Ryan Company. Bob insisted on going east to school and won admission to Dartmouth College in Hanover, New Hampshire.
That summer he accepted an invitation from his former camp counselor, a wealthy Yale graduate named Frank Scully, to work at a dude ranch Scully was trying to start on some land his family owned in Missoula, Montana. Bob took the train out West, spent the summer sharpening his horseman skills, and even found time for a first romance with a girl named Thora Maloney. He would remember his awe at seeing “plains that never ended — where one seemed to be becalmed in a purple ocean. As we got into the foothills of the Rockies and finally saw some of the high peaks I was aware of a lift of spirit that I shall never forget. It was strange to be so far from home and yet to feel as if I was coming home.”17
Back in Chicago he gathered his belongings for school and at long last left his parents behind. His father was pained to see him leave. “He didn’t get the point — packing off 1,300 miles to the state of New Hampshire when there were five colleges to be had within an hour’s drive,” Bob would write. “Mother must have sensed that I should go — though I hope she didn’t know how much I wanted to go.”18
At Dartmouth he pledged Psi Upsilon (one of his fraternity brothers was Nelson Rockefeller) and went out for track and football. But his real claim to fame was boxing: in his freshman year he won the college its first heavyweight title. His grades were unspectacular; he maintained a C average, studying Greek, French, English, physics, evolution, philosophy, and citizenship. The following summer he returned to Scully’s ranch, pursuing romance with another girl, Thula Clifton, and in the fall he played football again, though his career ended ignominiously after he broke his knee in a game against Columbia University. The injury threw his schoolwork into disarray, and in December 1928 he withdrew from all his classes without receiving any grades, standard procedure for someone flunking out.
For the next eight months Bob returned home to his parents, who had moved to a new apartment on Lake Shore Drive. Tim insisted that Bob work, so he got a job as a salesman, first for a steel company and then for a cemetery. “I’m offering a permanent product,” he would tell his customers.19 That fall he reenrolled at Dartmouth, starting over as a sophomore, and though he would continue to box, he had resolved to get serious about his studies.
A month after he returned, the stock market crashed. October 23 brought the first wave of sell-offs, then on October 29 — “Black Thursday” — the bottom dropped out. Crowds gathered outside the Chicago Stock Exchange, where a record one million shares changed hands in a single day. The Ryan Company was privately held and, at that point, worth at least $4 million. But each of the brothers was personally invested in the market, and they were all wiped out. All they had left was the promise of more construction work.
Even that seemed precarious: earlier that year Assistant State’s Attorney John E. Northrup had returned indictments against Ed Kelly and a dozen other men at the sanitary district, charging that they had defrauded taxpayers of $5 million over the past eight years and done a healthy business in bribes and kickbacks from contractors. “A well-greased palm was essential to doing business with the department,” wrote Kelly’s biographer, Roger Biles. “Some trustees received gifts of twenty-five cases of liquor a month from favored contractors.” Others “admitted financing lengthy European vacations with illegally solicited contributions.”20 Kelly would later concede to the IRS that from 1919 to 1929 his income was $724,368, though his salary for that period totaled only $151,000.
More than seven hundred people were called to testify, many of them against their will. Witnesses exposed gaping discrepancies between the district’s stated expenditures and what contractors were actually paid: the payroll was said to be padded by as much as 75 percent. The trial revealed that bids were submitted in plain envelopes that were later opened and altered so that favored firms could be awarded lucrative contracts. Elmer Lynn Williams, publisher of the muckraking newsletter Lightnin’, alleged that the district’s central auto service had provided high-ranking officials with “young women procured for these tired business men by an older woman who was on the pay roll. The taxpayers were charged for vanity cases, whiskey and the time of the ‘entertainers.’”21
None of the Ryan brothers was ever implicated, but the scandal soiled the reputations of everyone doing business with the district. Kelly escaped conviction only when the judge in the case, who was pals with a local Democratic boss, quashed the indictments