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The Winter Family gang coalesces during General Sherman’s devastating march through Georgia in the U.S. Civil War.

JOHN LEHMANN/The Globe and Mail

The Winter Family
Clifford Jackman
Random House Canada
332 pages

They say everyone loves a bad boy, and in his first novel, Guelph, Ont., lawyer Clifford Jackman apparently sets out to test that truism. The outlaw gang of The Winter Family is made up of really evil, really scary bad guys. These are not the loveable rogues of Butch Cassidy and the Sundance Kid, nor even the romanticized, Robin Hood-like robbers of the James Gang. Jackman's characters are drunks, sadists and psychopathic killers. The "good guys" in this novel – a bounty hunter, a couple of gang members with occasionally apparent consciences – are just relatively good, less bad, not quite so crazy.

Most of the story takes place in the years from the 1860s through the early 1890s, beginning in the U.S. Civil War. The gang coalesces during General Sherman's devastating march through Georgia, when they are enthusiastic participants in the murder, rape, theft and destruction generated by that campaign.

The "family" expands and contracts over the decades, but the half-dozen or so core members are led by Augustus Winter, who was viciously abused as a child and grew up into a sociopathic, Bible-quoting clothes horse with a reputation for merciless violence. Quentin Ross, his second-in-command, is a highly educated, erudite sadist and compulsive liar, even crueller than Winter. (After one particularly horrific and bloody incident in Georgia, resulting in the deaths of two women and two children, Ross says only, "Those people had valuable intelligence.") There are the Empire brothers, Charlie and Johnny, stupid drunks, uncontrollable looters and rapists, but fearless in a gunfight. A later addition is gifted young gunslinger Lukas Riddle, who worships Winter and will follow him anywhere, do anything for him.

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On the Family's somewhat less bad side are Fred Johnson, a gigantic ex-slave who took advantage of the fog of war in Georgia to kill his master with an axe. He reads books and tries to rein in the worst excesses of the other Family members. Bill Bread is a dead-eye shot with a nascent moral sensibility, which he manages to suppress with copious amounts of alcohol. Jan Mueller emigrated from Germany only to be conscripted into the Union army as he stepped off the boat; he was sent to war without a word of English, and rose to the rank of sergeant.

The novel moves in roughly chronological scenes from one era to another, from the misery of the Civil War to train robberies in the Deep South, hunting "Indians" to collect the bounty on scalps (or simply to clear acreage for white landowners), the destruction of whole towns and – in one of the more intriguing sections – helping the Republican Party fix the Chicago mayoral election of 1872. If you think politics is a dirty business now, get a load of this 19th-century U.S. election, with flagrant and unashamed ballot-buying, violence and intimidation, and citizenship on offer for those willing to sell their votes.

I don't want to make things sound grimmer than they are. The worst of the viciousness in The Winter Family occurs off-stage, and is viewed through its aftermath or from descriptions and even hints in dialogue. Even when the violence happens in plain sight, as it were, Jackman handles it with relative restraint. Winter's cruelty is established as much by how people react to his reputation as by direct portrayal. When a train's defiant engineer realizes that the Ku Klux Klan leader robbing his train is actually Winter, his resolve melts: "'My god,' the engineer said. His bladder released. The sound of urine hitting the floor was unmistakable."

The Chicago sections are especially entertaining, an up-close portrait of the young midwestern city with all its stink and filth, corruption and depravity, lawlessness and unruliness. The minute-by-minute descriptions of a hog-slaughtering operation are gut-churningly detailed (and, one supposes, symbolic), and the matter-of-fact, Tammany-style ward politics of the election ring absolutely true.

The physical descriptions of the U.S. West in the second half of the 19th century – towns, Indian villages, prairies – are nicely detailed and persuasive. But the real triumph is in the portrayals of the frontier's social dynamics. As the years pass, life becomes harder and harder for the Winter Family. By 1891, their situation is nearly impossible. "It was not like in the old days. There were fewer places to hide and their pursuers were stronger, angrier, more determined. … Everywhere they went had changed, and everywhere they went they were pursued. … The West closed down around them, as fences went up and herds of cattle swarmed over the plains and the Indians vanished. … All around them, pressing from all sides, the people, the people, the people."

It would be enough to make you sympathize, if not for the fact that the Winter Family is so resolutely unsympathetic. There are moments in the book when you might almost feel sorry for Augustus Winter, even root for him: When he visits his childhood home and relives the beatings from his drunken father; when he escapes in mid-winter, naked and wounded, from a pursuing posse of marshals and Pinkerton agents. But then, inevitably, he does something unforgivable, and the evil gang leader is back, as fascinating as any other complicatedly deadly thing. But you will not, cannot, love him.

Jack Kirchhoff is a writer and editor in Toronto.

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