With 30 percent of voters still undecided in the mayoral election, Portland is clearly not very keen on either Jefferson Smith or Charlie Hales. But let's put it in perspective: They definitely won't be as bad as these guys.


1. William Farrar (1862): "I have a soft spot for him," says local historian Dan Haneckow. At the beginning of Farrar's term, he told council he had to take a three-month leave for his business. Then he was never seen in Portland again. "No known photograph of him exists."

2. George Luis Baker (1917-1932): Mr. Baker proudly posed for a photo shoot with hooded members of the Ku Klux Klan and felt his greatest accomplishment as mayor was "removal of subversives" from the city by busting up the International Workers of the World.

3. George Frank (1894-1896): Frank handily won the election thanks to a flood that kept voter turnout low while he paid drunken repeat voters with free booze to cast ballots in every precinct they could, says Haneckow, who runs Portland history blog Café Unknown.

4. James Chapman (1867-1868, 1875-1877, 1882-1885): According to Portland Walking Tours guide (and Merc contributor) Joe Streckert, Chapman admitted to taking a bribe of about $1,000 in gold in exchange for making a political appointment. After the story got out, though, he didn't resign, saying, "Such bargains are made before every election."

5. Scandal Bonus! Terry Schrunk (1957-1972) and Neil Goldschmidt (1973-1979) were solid mayors... except for scandals that put all the current "driving-record, lady-punching" dirt to shame. Schrunk was accused—but acquitted!—of taking bribe money from a gambling boss, and Goldschmidt admitted to having sex repeatedly with a 14-year-old girl while in office. Hales and Smith have nothing on them.