Even the joyless, pitiful souls who spent this summer paying attention to a City Hall election still seven months away struggle to handicap the two top mayoral candidates, Charlie Hales and Eileen Brady.

Another candidate, state Rep. Jefferson Smith (D-East Portland), entered the race on Sept. 13.

Hales served a decade on the City Council and championed the Portland Streetcar before leaving office early in 2002. Brady, a first-time candidate, is a board member of a nonprofit and a businesswoman who helped co-found New Seasons Market. An early poll showed their favorability numbers are about the same (“Why Sam Adams Drifted Away,” WW, Aug. 3, 2011). 

Just as important, they’re very close in fundraising. By Sept. 12—only a few days after the candidates could officially file at the City Auditor’s Office—Brady had already raised $177,000; Hales, $155,000. Smith has a deficit of $3,400 in his legislative campaign account.

All three expect an expensive race—probably more than $1 million. In interviews with WW, Hales and Brady said they do not intend to voluntarily cap their campaign contributions, as some candidates have in the past.

Smith says he will refuse out-of-state donations from corporations and organizations (such as unions). “The race for mayor should not be an auction,” Smith says.

For all their superficial similarities, however, a close look at Hales’ and Brady’s campaign finance reports reveals some important distinctions.

Hales has pulled in bigger donations and snagged more money from out-of-state donors, leaning heavily on his business connections and links to mass transit. Brady has so far raised more than Hales by collecting far more small contributions and by attracting more donations from women.

In this race, it’s the really big checks—far bigger than federal campaign spending limits would allow—that have fueled both campaigns.

Brady’s biggest donations have come in at  $10,000: from New Seasons co-founder Stan Amy; and PM Financial Services, a mortgage company owned by Darla and Kali Placencia in the Chicago area, where Brady grew up. 

Five-digit donations may start to look small in Portland. Hales already has two $25,000 donors: investor David Nierenberg of Camas, Wash., and California-based contractor Stacy & Witbeck, which has laid light rail and streetcar tracks all over Portland.

Brady has made up for slightly smaller checks with a donor base that’s three times as large as Hales’, although both draw from a similar pool of executives, investors, attorneys and other white-collar professionals.

Perhaps more important, Brady’s donors also include a much greater share of women. According to a recent Riley Research Associates poll, Portland women are not only a slightly bigger share of registered voters, they are much more likely to vote. 

It may have helped that Brady won a crucial endorsement from EMILY’s List, a national political action committee that rallies donors for pro-choice Democratic women. On Sept. 21, Hales is throwing a fundraiser with prominent female supporters in Southeast Portland.

View Eileen Brady donations 9-12-11 in a full screen map

View Charlie Hales donations 9-12-11 in a full screen map

View Jefferson Smith contributions Sept. 9 2011 in a full screen map

Note: The map of Jefferson Smith's donors draws from his legislative campaign, not his new mayoral bid. It's presented here for the benefit of the curious. State campaign finance laws allow candidates to use the same funds for different races, should they attempt to switch jobs.