This first novel by Towles who is a principal in a Manhattan investment firm is not great, but it's interesting enough to warrant a read. The book starts with a prologue set in 1966. A woman and her husband are at a photography show featuring pictures snapped on public transit during the Depression. The woman is struck by two photos of Tinker Grey, a man she knew in the late 30s. Her husband believes the pictures tell a tale of rags to riches but she points out the opposite is true - the picture of the well-dressed banker pre-dates the picture of the downtrodden man.
The remainder of the book is the woman, Katey Kontent, looking back at the period when she knew Tinker - from the last day of 1937 to the last day of 1940. When the story begins, Katey lives in a boardinghouse for women, with a roommate, Eve, a transplant from Indiana trying to make it big in the city. Katey's a secretary in the pool at a large New York law firm. The two women try to make a few dollars last through New Year's Eve by listening to a jazz band in a "hole in the wall" bar when Tinker enters their lives. He's waiting for his brother who never shows up and he befriends the two women. It's clear from the start that there's more chemistry between Tinker and Katey but Eve sets her sights on him and when an accident occurs the two end up together, much to Katey's disappointment.
But Katey doesn't let it stop her, she has relationships with two other men, quits her job and finds one as an assistant at a magazine and slowly climbs her way up the social ladder. Along the way we find out her unlikely patron is a woman in an unusual relationship with Tinker. When Eve rejects Tinker's marriage proposal, he and Katey get together briefly but she discovers how he's accumulated his wealth and cannot cope with it. Neither can he and he turns his back on the wealth and disappears into New York's working classes.
I also found myself wondering throughout the book, who Katey ends up marrying - and I was surprised to discover that he was a bit player she encountered in the late 30s but did not reconnect with for several years.