As an undergraduate at Dartmouth College, Ryan became an intercollegiate boxing champ and ran for class marshal on the slogan “Rum, Rebellion, and Ryan.” Robert Ryan Family

      Without the athletics, his academic performance improved; he made Phi Beta Kappa in his junior and senior years, wrote an essay on Shakespeare that was anthologized in a collection of undergraduate writing, and won a hundred-dollar prize for his experimental one-act play The Visitor, whose title character was the grim reaper and whose one and only performance took place in the college’s Robinson Hall. Now twenty-two, Bob had hung onto his blissful ignorance for as long as possible, but he began to understand that he would be graduating into harder times than any he had ever known. The Ryans’ life of luxury had evaporated as the country spiraled into depression. Tim wanted Bob to come home and help with the business, but Bob resisted. He would do anything but seal himself up inside an office.

      After graduating in June 1932, Bob took what little money he had and moved to Greenwich Village with two fraternity brothers, intending to find a job as a newspaper reporter and work on his playwriting. A third of the country was out of work, and along the streets of New York people queued at breadlines and soup kitchens. Bob couldn’t figure out what he wanted to do with his life; he only knew he couldn’t go into business. He fought a professional bout under an assumed name to raise some cash, but otherwise the boxing went nowhere. A girlfriend got him gigs modeling for true-confession magazines and department store ads — he later claimed to be the first man in America to model French jockey shorts — but his pals gave him so much grief over this that he quit. For a while he worked as a sandhog, pushing rock barges through tunnels under the Hudson River.

      In this economic climate the pampered young man oscillated between realism and sheer fantasy. Some pals from Psi Upsilon persuaded him to come in with them on a gold mine in Libby, Montana, and Bob moved out West to prospect with a friend. The living was rough; they had to break ice on a stream for bathing water. After four months they had managed to extract about eight dollars’ worth of gold. When Bob heard about a cowpuncher job in Missoula paying that much every week, he gave up on the mine, and eventually he returned to New York City, wearing a long beard and hitting up his classmates for money to get back on his feet.

      Magazine profiles would offer differing accounts of how Bob managed to wind up a sailor aboard The City of New York, a diesel freighter making runs to South Africa, in 1933. According to one, he was strolling along the Brooklyn waterfront one day, visiting a friend, and when he saw the ship loading on the wharf, he impulsively asked for a job.³² According to another, he “accepted drinks one night from a jovial tramp steamer captain” and “woke next morning bound for Lourenzo Marques, Portuguese East Africa.”³³ In any event, Bob shipped out as an engine room wiper, cleaning up oil that leaked from the cylinders and various pumps, oiling the pumps, and fetching coffee. Owned by the private Farrell Lines, The City of New York headed down the East Coast to New Orleans and then across the Atlantic, carrying manufactured goods. It probably docked in Cape Town, East London, and Durban, and it returned to New York two or three months later with shipments of raw asbestos or chrome.³⁴

      Bob might have been surrendering to his love of Melville and Eugene O’Neill, who had written of the seafaring life in Anna Christie and The Hairy Ape. He spent more than two years at sea, collecting stories of hardship and adventure. The equatorial heat was unbearable; once he had to intervene when a delirious female passenger tried to push her baby through a porthole. Another time, after the ship’s store of food spoiled, he subsisted for days on lime juice.

      Whenever Bob heard from his parents, the news was grim. In December 1934 his Uncle Tom died, leaving the presidency of the Ryan Company to Tim. Soon after that both Joe Ryan and John Ryan died. The pressure of the construction industry was crushing them out like the cigarettes Bob now smoked daily. In January 1936, not long after returning home from a run, he received a phone call from his mother: his father had been hit by a car, and Bob was to return to Chicago at once to look after him and help out with a subway tunnel project. Bob made an inglorious return to Chicago as a common sandhog, pushing rock barges beneath the streets of the city by day and struggling to understand the business by night.

      Tim’s accident had exacerbated a heart condition, and on April 27, 1936, he died of a coronary occlusion at Passavant Memorial Hospital. He was sixty. Writing to his children, Bob would quickly recount the stock market crash and the tunnel disaster, adding, “I am sure that both of these events caused my father’s early death.”³⁵ Tim was laid to rest in Calvary Cemetery in the north suburb of Evanston, beside his little son Jack.

      Bob knew he had to look after his mother and made a game effort to help his uncle Larry, now president of the Ryan Company and the last surviving brother at the firm. But he wanted out of the tunnels: one time, as he was breaking up rocks with a sledgehammer, he turned over a rock to find an abandoned dynamite charge. Another time he worked forty-eight hours straight when a power plant failure imperiled the air pressure in a tunnel. Eventually, he quit the company, drifting from one job to the next. One oft-repeated story had him working as a collector for a loan shark on the blighted West Side and, moved by the poverty he saw, coming back to return one family’s money. He was working as a gang boss on a WPA road paving crew for thirty dollars a week when his uncle Larry Ryan died in December 1937, only fifty-five years old. The Ryan Company would endure into the 1940s, but there was nothing left of the brothers now except their name.

      Frustrated with her son’s career drift, Mabel finally called on Tim’s old friend Ed Kelly, who had not only survived the sanitary district scandal but ascended through a city council vote to become mayor of Chicago. After Anton Cermak was fatally wounded during an assassination attempt on President-elect Roosevelt in February 1933, Kelly had been pushed through the council by his old friend Patrick Nash, the Twenty-Eighth Ward alderman, and they controlled a formidable vote-getting operation that gave them enormous power over the city. Bob would remember Big Ed Kelly as an avatar of ward politics and no dreamer. One night in 1928, when Bob was home from college, he had been sitting in his parents’ living room when Kelly came calling for Tim, having just met Al Smith, the progressive New York governor and Democratic nominee for president. “He’s talking about things like welfare and human rights and all that shit,” Kelly complained.³⁶

      As mayor, Kelly had relaxed enforcement of gambling laws; according to the Chicago Crime Commission, the administration pocketed $20 million from organized