‘Rough Sleepers,’ by Tracy Kidder

The myth of Sisyphus appears in Tracy Kidder’s “The Tramp,” which tells the story of a doctor who works among Boston’s homeless population, and it’s an apt story. The themes of the book state that Sisyphus was always striving towards a goal he could never reach, and is often seen as a perpetually frustrated man. But what if Sisyphus was energized by challenges? What if he pursued struggle?

This may be a rationalization for Dr. Jim O’Connell, who has spent decades finding people with health care and housing, and he knows that many will fall backwards and more needy people will show up the next day. But it seems to be working for him.

O’Connell, often referred to as “Saint Jim” — though he was never one himself — left Harvard Medical School and took a detour into what he thought would be a year of caring for the homeless, only to discover that it was His life’s work. Now in his 70s, he’s still “calling on the homeless,” as CBS News put it in a profile.

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O’Connell is a fascinating protagonist. Kidd spent years following the tireless doctor’s work, examining patients under bridges, handing out $20 bills in parks, and imploring patients to go to emergency rooms (and the legislature to provide funding).

There is evidence that Kidd digs behavior that contradicts the “Saint Jim” moniker, but the best he can come up with is to hear O’Connell swear once (the marriage ended somewhere along the way, but we never see She doesn’t know what happened). The picture that emerges over the course of the riveting, inspiring “Wanderer” is that O’Connell is not just one of the good guys, but a vibrant, self-critical, even funny good guy.

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About that mysterious marriage, though. Kidd’s best books, including “The House,” “In Schoolchildren,” and “The Soul of the New Machine,” have built-in timelines: from design to moving in and creating a home, a year of classroom life, or deadlines for designing computers. Without them, Kidd is no good at structure.

It’s hard to gauge the chronology of “The Tramp” spanning several decades. O’Connell’s longtime colleagues pop up about two-thirds of the way through the book, and it seems like we’re supposed to know who they are, but we don’t. Others disappear without explanation, with O’Connell’s second (I think?) wife being a particularly confusing cipher.

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Maybe Kidd’s deal with O’Connell not to interfere in his private life is probably for the best. In fact, it’s hard to imagine O’Connell having any time for a private life, as Kidd describes all 18-hour workdays with humility and empathy in “The Tramp.”

Chris Hewitt is a features writer and critic for The Star Tribune.


Author: Tracy Kidd.

Publisher: Random House, 320 pp., $30.


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