Illustration by Ryan Alexander-Tanner

THE QUESTION before Michael Simon, the US District Court judge weighing Portland's controversial police reform settlement with the US Department of Justice, seems pretty simple.

If Simon decides the proposed reforms are "fair, reasonable, and adequate"—that they justly address a federal finding that our cops have engaged in a pattern or practice of using excessive force against people with mental illness—he will let the agreement officially take effect.

But if Simon agrees with the dozens of citizens and advocates who packed his courtroom last month, and decides the settlement falls short? He will be compelled to reject it wholesale.

Simon is the first to admit he's not allowed, technically, to order specific changes. So a rejection could force the city and the feds, and the city's rank-and-file police union back to the negotiating table. Or not. A trial could loom—and real, needed change could be even further delayed.

But nothing about this saga has ever been as simple as it seems.

Simon, at least in this case, has made a habit of creatively exploring the outer limits of his judicial leverage. And he appears to be doing that again—actively charting a middle course meant to improve the deal, by weaving in changes, without destroying the tenuous bonhomie between the parties that led to a deal in the first place.

He gave his first hints during last month's day-and-a-half-long "fairness hearing." Simon listened intently to all the harsh testimony—complaints about cops overseeing cops and the lack of agency in Portland's current civilian-oversight system.

Then, after reminding the feds, the city, and the police union that he could easily plunge them all into legal purgatory for several more months, Simon graciously and cheerily offered an out: the chance to submit amendments.

They all said no, politely. They want this over with.

But Simon isn't taking no for an answer. On Friday, February 28, he entered a compelling document into the court file—13 incredibly persnickety questions about the proposed reforms and Portland's current police oversight system.

"In light of some of the comments raised during the fairness hearing," Simon wrote in what might be his most difficult question, "do the parties believe that the Independent Police Review Division and the Citizen Review Committee provide a fair, reasonable, and adequate process by which citizens can make complaints against Portland police officers and have confidence that complaints will be adequately investigated and resolved?"

Beyond that, Simon's asking about an already out-of-date provision promising new mental health treatment centers by mid-2013 ["An Empty Mandate," News, Feb 19].

And, if Simon does decide to say yes, he's looking for some creative ways to increase his oversight.

It's another way of pressing the point that at least a few amendments might be helpful. Also, it's another way of making sure the wider community—if Simon gives it his blessing—says yes, too.

"He's asking them, 'Are you sure?'" says Dan Handelman of Portland Copwatch. "We really want to see those changes made. But it's nice he's going to at least force them to respond."