Long after Tammany Hall was as dust, and the once-famous bosses William Vare of Philadelphia and Tom Prendergast of Kansas City mere footnotes, Chicago’s political machine endured. Indeed, it has prevailed, still absorbing every emerging special interest and ethnic group into its ranks.

“Lords of the Levee” (Northwestern University Press, 385 pages, $19.95) by Lloyd Wendt and Herman Kogan, republished this month by Northwestern University Press with a delightful and affectionate foreword by Kogan’s son Rick, captures the birth and rise of that machine through the lives of Aldermen John “Bathhouse John” Coughlin and Mike “Hinky Dink” Kenna, longtime bosses of Chicago’s old First Ward and its infamous Levee District.

One unexpected benefit of Martin Scorsese’s “Gangs of New York” has been a renewed interest in colorful urban history. Like Herbert Asbury, who wrote “The Gangs of New York” and other classics of the urban underworld, Wendt and Kogan were working reporters for the Tribune and the Sun-Times, respectively, who knew good stories when they found them and knew how to tell them in crisp, fast-moving prose, rich with irony that never declines to sarcasm. Their skillful, witty writing compellingly captures certain universal truths about American machine politicians – men for whom politics is no more than getting and keeping power for personal and economic advancement, for whom issues are inconvenient irrelevancies.

Bathhouse John, whose nickname stemmed from his early career as a rubber in a Turkish bath, was a born front man. A big, flamboyant gladhander, the exhibitionist Coughlin loved the limelight. He dressed in loud, clashing colors – purple frockcoats and vests of lime green with neon orange stripes, buttoned with miniature conch shells, for example – and often broke up council meetings by declaiming his astonishingly bad verse: “Two Thirsts With but a Single Drink,” “They’re Tearing Up Clark Street Again,” and “She Sleeps at the Side of the Drainage Canal,” to mention a few. But his fool’s pose never harmed him with the voters – he died undefeated – and his facade of genial buffoonery obscured his greed and dishonesty.

When Mayor Carter Harrison asked Kenna, Coughlin’s partner in crime, “Tell me, Mike, do you think John is crazy or just full of dope?” Kenna replied, “To tell you th’God’s truth, Mr. Mayor, they ain’t found a word for it yet.” That was a luxuriance of words from the taciturn Kenna. Known as “The Little Fellow,” Kenna, who began his working life as a newsboy, was born for the backroom: short and thin, with a wispy mustache, quiet, reserved, and observant.

Entrepreneurs of power, cunning and ruthless, these outward opposites rose to prominence and wealth through hard work and persistence. They registered thousands of drunks and derelicts to vote from phony addresses in the First Ward’s fleabag hotels, whorehouses, and bars. Their energetic campaign workers dragged the bums to the polls for 50 cents to $5 a vote. And once their power was secure, they established a protection racket for whores and gamblers, complete with lawyers on retainer to bail out their clients.

By the 1890s, as the Chicago Inter-Ocean wrote, they ruled “a vast illicit empire of 400 opium resorts, 100 gambling dens, 7,000 saloons and other haunts of sin and over a population which is 18 percent criminal.” Their annual fund-raiser, the First Ward Ball, brought together some 15,000 “madams, strumpets … female impersonators, tramps, panhandlers, card sharps, mountebanks and pimps, owners of dives and resorts, young bloods and ‘older men careless of their reputations’ … in “an ever-increasing drunken revel” at the Chicago Coliseum. Even here, Coughlin and Kenna squeezed constituents for free booze and food: The waiters had to pay $5 for their jobs, hoping to recover their investment through drunken guests’ generous tips.

Luckily for Bathhouse John and Hinky Dink, they entered public life as new technologies required privately owned utilities – gas, electric, and water mains, telegraph and telephone lines, streetcars, and elevated railroads – to have the use of the public streets. A permit for such use is called a franchise. In Chicago, franchises were awarded by the City Council. This meant they went to the highest or best-connected bidder, such as trolley king Charles Tyson Yerkes, who knew $1 million in bribes could be quickly recouped at the fare box.

Besides cash on the barrelhead, Yerkes and his rivals offered long-term payoffs, such as placing contracts for insurance, coal, and supplies with companies controlled by aldermen. All business permits were also approved by the council, which deferred to individual aldermen in approving or disapproving permits affecting their ward. Coughlin and Kenna milked even pushcart licenses or permits “to erect a barber pole.” Thus, within a few years, both men became multi-millionaires.

Coughlin and Kenna never left office, but gradually lost the power to the city’s Democratic machine and its underworld allies. Occasionally, despite the best efforts of Coughlin and Kenna and their allies, the voters elected an honest mayor who enforced the laws against gambling and prostitution. More often, even mayors friendly to Bathhouse John and Hinky Dink surrendered to reformers’ demands for suppressing the Levee’s open and notorious vice. Closing down a whorehouse or gambling den, even for a few weeks, meant massive economic losses to their proprietors.

Realizing that Coughlin and Kenna couldn’t consistently protect them, more intelligent criminals, such as onetime Kenna bagman Big Jim Colosimo (who controlled more than 200 whorehouses) realized, long before Mao, that political power could flow from the mouth of a gun. Al Capone, Colosimo’s eventual successor, made explicit who was the real boss of the Levee, leaving Coughlin and Kenna as the mob’s well paid errand boys. Coughlin died in 1938, aging, arthritic, and obese, having squandered nearly everything on horses, bad investments, and women. Kenna, who died rich in 1946, paid for his funeral.

Kudos to Northwestern University for reviving Coughlin and Kenna – and Wendt and Kogan, whose books reward reading and rereading, both for entertainment and for clear insight into the American political demimonde, where public service and private enrichment meet.

Mr. Bryk last wrote in these pages on slavery in New York.