IN THE BATTLE for Mayor Sam Adams’s job, wannabe candidates are gearing up for next May’s primary. But who should really run? We’re dreaming of a race between Portlanders too smart, too weird, or too dead to want the job. Consider these past overlords for a start—and send ideas to [email protected]. We’ll publish the best.

THE BIO Founding father, mayor 1854–55, early beard-chic adopter
CLAIM TO FAME Built a vast estate on “forfeited mortgages and defaulted loans”
APPEAL A go-getter who started out selling gin on Front Street, Ladd could be called the ancestral father of cart entrepreneurs, artisan bartenders, and microdistillers.
WHY HE COULD NEVER WIN Ladd’s Addition broke the sacred Portland grid—creating generations of enraged drivers. 

THE BIO Portland’s first female mayor, 1948–1953
NICKNAME “No Sin” Lee
APPEAL Lee crusaded against gambling and prostitution, thus angering the city’s clubby elite. Fierce!
WHY SHE COULD NEVER WIN Her statement that “the forces of evil are pretty deep-seated in this city” could alienate Portland’s powerful Wiccan, Santería, and steampunk constituencies. 

THE BIO A wildly entertaining, mostly incompetent Oregon governor (1887–1895) and Portland mayor (1896–1898)
NICKNAME “His Eccentricity”
APPEAL Cranky Sylvester would court Portland’s Nader-style left-wingers. He denounced President Cleveland as a “Wall Street plutocrat” and once moved Thanksgiving up a week to protest federal policies.
WHY HE COULD NEVER WIN On the other hand, his support for the Confederacy and anti-Chinese policies just might not fly in modern-day Portland. 

THE BIO A cigar-chomping good old boy who ruled Portland during World War II
ONCE (CHARITABLY) DESCRIBED AS “Tough. Able. Demanding.”
APPEAL After decades of touchy-feely righteousness, Riley could put Portland back in touch with its wild side.
WHY HE COULD NEVER WIN Riley’s habit of stashing up to $60,000 a month in vice payoffs in a City Hall safe would deplete the city’s bioswale impact study fund.

THE BIO Mayor 1911–1913 
WHY HE’D FIT IN “A bland but dedicated public servant,” according to historian E. Kimbark MacColl 
APPEAL Faced with a morals crisis—“The trains are loaded with gamblers … touts, pimps, confidence men [and] common women,” the Oregonian reported—Rushlight acted with the characteristic boldness of Portland mayors. He appointed a commission.
WHY HE COULD NEVER WIN His failed proposal to create a red light district hints that he might have trouble getting anything done.