an only child,” he would write years later, in a letter to his own children. “Two big grown-ups are beaming in on him all the time — even when he isn’t there. It is a feeling of being watched that lingers throughout life.”13 He hid in the darkness of the movies, spending countless afternoons at the Riveria Theater on Broadway or the smaller Bryn Mawr near the “L” stop. The charm and dash of Douglas Fairbanks were his greatest tonic, and he never missed a picture: The Mark of Zorro, The Three Musketeers, Robin Hood. Bob had seen how motion pictures were made and was fascinated by the results. Yet he could barely conceive of the movies as an occupation; his father and uncles considered the Ryan Company a legacy for their children.
After Bob graduated from Swift in 1923, his father pulled some strings to get him a summer job as a fireman on a freight locomotive, which satisfied the thirteen-year-old boy’s appetite for freedom and Tim’s desire that he learn the value of a dollar. Rumors of petting parties at the local public high school had persuaded Mabel that Bob needed a private education, and that fall his parents enrolled him at Loyola Academy, a Jesuit college prep school for young men that was located near the Loyola University campus to their north. The experience would shape him not only as a person but also as an artist.
Loyola was heavily Irish Catholic, the sons of an aspiring middle class, and the class of 1927 would produce an unusual number of Jesuit priests. Tim must have been 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
