Campaigning in 2008, Multnomah County Sheriff Bob Skipper promised he'd make "major personnel changes" in an agency that had been slammed by a special grand jury for entrenched leadership and failed management.
Skipper replaced Sheriff Bernie Giusto in July 2008 after Giusto resigned under investigation for lying to the public. And Skipper ended up winning a landslide victory a few months later to finish the last two years of Giusto's term.
But a year after that November 2008 election, it's Skipper who must step down Nov. 5 for twice failing an open-book test to gain his state police certification at age 70. He leaves at the same time that prosecutors are wrapping up a criminal investigation reaching up to the highest levels of Skipper's command staff.
There's also the fact that Skipper leaves with nearly all his top managers still dug in to the same spots. That's especially troubling in an agency with the critical task of running jails that have long suffered from mismanagement. The 2007 grand jury report concluded top commanders "grew up in the current jail system and are hesitant to change it."
True, Skipper had already switched the heads of his two jails before the election. He's shuffled other jail personnel and reassigned or pushed out 12 lieutenants. But for top management, the agency's organizational chart looks almost identical to the way it did the day he was elected.
Skipper's scorecard on other fronts is mixed. He failed to implement performance evaluations this year as he promised a grand jury, though his office blames the county for the delay. Skipper did, however, cut rampant abuse of sick leave and overtime.
"I think I did enough to get the job done without having people feel like I've hit them with a hammer," Skipper says.
In a twist, it's one of the few top-level moves Skipper did make that promises to cause headaches for the interim sheriff, Lt. Dan Staton. As Skipper rides away, he leaves accusations of a criminal coverup Staton will be left to clear up.
Those allegations have been whispered among sheriff's deputies for much of this year and are now the subject of a criminal investigation by the Multnomah County District Attorney's Office. But they have never before been made public.
While Skipper has been credited for improving morale, the allegations that he retaliated against a captain in order to cover up for a senior officer threatens to stain his legacy.
Skipper denies any wrongdoing and insists he's leaving the agency much improved after Giusto's days.
"There was really only one way to go, and that was up," Skipper says. "I feel really good about that."
The current allegations date back to Giusto's scandal-ridden reign. And just as Skipper himself must quit after failing tests to regain his state police certification after 13 years of retirement, the alleged coverup involves another top cop's efforts to get certified.
In 2006, Giusto shuffled assignments to put his former head of corrections, Chief Deputy Tim Moore, in charge of law enforcement. That meant Moore had to return to the police academy and spend several weeks in field training back at the sheriff's office.
Moore finished the academy in October 2006. But according to a complaint filed with the state Department of Public Safety Standards and Training, Moore never completed his field training. The complaint says Moore asked Capt. Monte Reiser to fill in his training manual without Moore actually completing the requirements.
Moore and Reiser both declined to comment due to the ongoing investigation.
Word of the allegations spread through the sheriff's office. In February of this year, Capt. Brett Elliott filed a complaint with Skipper. Skipper says he responded by putting a gag order on Elliott and sending the complaint to the DA's office for investigation.
In June, an anonymous complaint to DPSST alleged Moore, Reiser and Skipper committed a raft of felonies, misdemeanors and administrative violations in connection with Moore's certification, including forgery, conspiracy and tampering with records. DPSST Deputy Director Eriks Gabliks says his agency will review the case after the DA's office completes its investigation.
The complaint also alleges Skipper retaliated against Elliott in April by taking him out of his old job as patrol captain and putting him in charge of courthouse security—which, if true, may have been a violation of the state whistle-blower protection law.
Skipper denies the move was retaliation.
"I did not move him for discipline. I moved him for the good of the department," Skipper says. "I felt that Capt. Elliott was spending more time running around talking about the [training] book than he was doing his job."
Elliott declined comment, saying he's still under Skipper's gag order.
Staton and retired Lt. Bruce McCain have filed to run for election next year to finish Skipper's term. The Multnomah County Board of Commissioners will set a date for that vote Nov. 5.