It's been 16 years or so—the end of Vera Katz's second term—since Portland's had an incumbent mayor running for re-election. Put that way, it seems like an astounding amount of time.

But that streak appears over.

About a month or so after Mayor Charlie Hales demurred on the subject of re-election, he's just reported a very serious contribution with the state elections office: $5,000 from John Bollier, the president of prominent transportation contracting firm Stacy and Witbeck.

Hales' spokesman, Dana Haynes, reminded me that his boss has yet to announce his next steps but said he'd check again to see if anything had changed. But reading between the lines here, it's hard to see Hales not about ready to leap in.

For one thing, Bollier appears somewhat tight with Hales. In 2012, when Hales was finding creative ways to get around a self-imposed $600 campaign donation cap from individuals and organizations, Bollier was one of the Hales campaign's "deputy prospects"—charged with helping collect checks and raise thousands from other big wheels in town.

And they've also apparently seen fit to talk business together after Hales was elected. In 2013, the Oregonian reported Hales and Bollier meeting about land acquisitions along the new light rail line to Milwaukie. After those meetings, the paper reported Hales had ordered staff to expedite permit applications submitted by Stacy and Witbeck.

Hales has been sending other signals he's not looking to be Portland's third consecutive one-term mayor—like getting cozy with labor leader Tom Chamberlain at his State of the City speech, announcing some $15 minimum wage news that was also applauded by 2012 backer Service Employees International Union.

The mayor did confirm last month that he's been asking for donations. And he's already recorded some small ones in the past few days. But this one's serious. Serious enough that it strains credibility to say he's still just thinking about a chase for a second term.