It's a gift to reporters and interviewers—and it's certainly refreshing—but Jefferson Smith has yet to fully master one of the subtler secrets of politicking: Running his thoughts through a filter before saying them aloud or, worse, writing them down and emailing them to a reporter in the wee hours of the morning.

Sometimes that can work for him. For instance, this week's Hall Monitor offers a sampling of cortandfatboy's 70-minute must-listen interview with Smith, posted Monday. As I wrote in the column, it comes off like a "heartbreaking exit interview" that engenders a little bit of sympathy.

Smith earns a few points for introspective, painful honesty—admitting he was too scared to mention his 1993 assault citation on his own, even though he thought about it doing so a few different times. At one point, he said, he considered revealing it during a speech to domestic violence agency Raphael House. And then again during his University of Oregon commencement address. He's clearly aware that the reticence and fear may have doomed his chances of beating Charlie Hales.

He also called out newspapers in town for spending months and years digging into his "sexual history," and revealed that since WW broke the story about the college party, reporters have been going back to everyone he's known asking them again whether they ever remember Smith being creepy, a bully, or a pervert.

"Did he ever look at you funny? Did he ever touch you in a way you didn't like?" he said. "I've known 1,000 people... Can they find 10 who will say 'I hate that asshole'?"

But Smith also let loose with some other sentiments that might have better served him staying private. He hints there's a chance he gets his "tail kicked" and muses on the possibility that he and his wife might leave Portland if he really does lose the mayor's race. That can't be reassuring to the staffers working to keep his campaign alive.

Meanwhile, hours after sitting down for the podcast, Smith decided he wasn't quite finished unburdening his soul. As the Oregonian reported late last night, Smith—at the ridiculous, no-good-comes-from-it time of 1:32 in the morning—actually pressed send on a personal letter to city hall reporter Beth Slovic.

In the letter, Smith laments the paper's run of unflattering stories about his personal life but also promises to try to work together with Slovic if he's somehow elected mayor. He also mentions a talk with WW's bulldog, Nigel Jaquiss, on how the Oregonian went about reporting on Smith's driving record.

"In any event, my reputation has been under some deep attacks over the past 2 months," Smith wrote to Slovic, according to the paper. "I don't know if I'll recover or not. I know that a piece of that is your job."

How did such a personal letter wind up published in the paper in the first place? Smith made a classic mistake by failing to note the thing was off the record before letting the words fly. He sent followup emails trying to make that clear, but it was too late.

The Oregonian isn't in the business of giving troubled candidates the benefit of the doubt, and Slovic dove through the gap between what Smith clearly intended and what he wrote. Or, rather, what he didn't.

If that feels like a technicality that might not have been turned against a candidate or source the paper might be more worried about burning, consider also that Smith has been in politics long enough to know better: If your letter is about "trust" issues involving a media outlet, then don't send that kind of letter to that same media outlet—on or off the record—in the first place. (And, really, I don't think the paper would've spared Hales or anybody else.)

"I suspect our contact will be limited over the next 3 weeks," Smith also wrote. "I don't suspect a single email will do that much to impact trust either way (and I do have real concern that the paper's editorial perspective is driving the news side). But I have wanted to send some word."