Once there was an aspiring young political strategist who disrupted a Chicago campaign event for a rival party candidate by inviting homeless to it with promises of free food, drink and more.
Republicans this election season have been attacking "Chicago-style politics" with relish, and such shenanigans might seem to fit into that low-road legacy. Except the strategist in question was a college-aged Karl Rove, who grew up to become one of the most influential players in the GOP.
With Chicagoan Barack Obama in the White House and his hometown famed for cutthroat politics, it was perhaps inevitable that rivals would seize on guilt by geography to try to discredit him.
The city's latest star turn as GOP villain began in recent days as Mitt Romney, Obama's all-but-certain challenger in November, fumed while Democrats intensified attacks on his finances, tax returns and record as a private equity manager.
"Chicago-style politics at its worst," the former Massachusetts governor and Bain Capital owner declared in a refrain quickly picked up by his campaign surrogates.
Ed Gillespie, a former Republican National Committee chairman, accused the Obama campaign of "classic Chicago-style politics" by trying to splatter mud over Romney's credentials.
To Rove, the attacks on Romney were "gutter politics of the worst Chicago sort."
Former New Hampshire Gov. John Sununu took it further: "Can you imagine coming out of Chicago politics, where 'politician' and 'felon' are synonymous? You've got two governors in prison today," he told CNBC, conflating the misdeeds of Chicago Democrat Rod Blagojevich with those of Downstate Republican George Ryan.
Asked to elaborate on what the Romney camp means when it invokes Chicago in its attacks on Obama, a senior aide to the Republican declined to comment, saying he did not want to smear an American city. Instead, he pointed to Sununu's comments.
Indeed, the term Chicago-style politics and its variations have become a form of political code for Republicans, never quite saying what they mean but leaving the clear impression that the city is a breeding ground for corrupt political hacks. And — by the way — Obama is from there.
To which Rahm Emanuel, Chicago's mayor and Obama's former chief of staff, responds:
"When their ideas of today's middle class are rooted in the J.R. Ewing family on the remake of 'Dallas,' it's no surprise their idea of Chicago politics comes from watching "Boss." They need a reality check on both fronts."
Political scientist Dennis Goldford, an expert on presidential politics at Drake University in Des Moines, Iowa, said the Republican imagery is an attempt to insinuate that Obama is a disciple of a throwback big-city political organization built on muscle and seediness.
"It strikes me as odd, because Obama was really not part of that old-style Chicago machine," Goldford said, adding that the strategy seems geared toward swaying older voters who remember lore about the Richard J. Daley era in Chicago.
"But for college students, history is yesterday," he explained.
Politically, there's less risk for Republicans ripping Chicago than virtually anywhere else in the country. The city votes reliably Democratic, and Chicagoans have been known to take a perverse pride in their city's tough-guy political persona.
Even Obama has played it up in the past. During his 2008 run for president, he quoted memorable dialogue from the movie "The Untouchables" in which Sean Connery describes the "Chicago Way" as: "He pulls a knife, you pull a gun."
And without question, Chicago has seen a goodly share of high- and low-profile officials and operatives shipped off to prison over the decades, and Republicans would like to prod voters into thinking that some of that dirt surely must have rubbed off on Obama.
But political wrongdoing knows few geographic bounds. On a per-capita basis, North Dakota endured more than twice as many federal corruption convictions as Illinois over the last decade, according to Justice Department data. But politicians don't complain about North Dakota-style corruption.
Chicago may be in the cross hairs of conservative political stereotyping because of Obama, but the city has company.