Deschutes County Interim Sheriff Rupert says he’s projected to save taxpayers $1 million in the coming fiscal year. Yet some of these cost-cutting measures run the risk of financial pitfalls down the road.
Deschutes County Commissioners approved the $72.16 million budget for the Sheriff’s Office on June 17, which is about 16% of the County’s overall budget of $446.1 million for FY 2027. The DCSO’s budget ticked upwards by 4.76% since last year. In a press release last week, Interim Sheriff Ty Rupert said he’s found $1 million in projected savings.
Rupert is running a campaign for Sheriff in the November Election that centers on fiscal mindedness. Rupert told the Source that his previous career as a corporate vice president has given him the nuts-and-bolts know-how to reduce costs and boost operational efficiencies.
The projected savings have allowed Rupert’s office to balance the budget and add four newly hired deputies to the county’s adult jail.
Of the $1 million in projected savings, the DCSO told the Source that about $300,000 of fat has been trimmed from the DCSO previous administrations’ excesses. Past sheriffs have been accused of some controversial spending, which included a $3,000 slushy machine, for example, or a third-party travel agency.
In conversation with the Source in November, Rupert mentioned how paying invoices within 10 days of receipt generally allows for a negotiated discount of 1 to 2%. Those discounts, granted by various vendors, are projected to save the DCSO $25,000 each year. Nixing the travel agency and handling bookings in-house will free up $65,000 each year. Foregoing new vehicle graphics will save $14,000, and tasking the DCSO Automotive Unit with the install of 100 new in-vehicle Axon Fleet 3 cameras (instead of hiring vendor technicians) rescued $83,000.
And eschewing the automated license plate reader technology, which got the Bend Police Department in hot water last year when federal immigration authorities queried its database almost 300 times last year, will save taxpayers $74,000 annually and $372,000 across the five-year, $2.4 million contract, the Source reported. DCSO patrol vehicles will be rolling with the new Axon gear by November.
Rupert has shaken down the lion’s share of projected savings — $700,000 — by not backfilling spendy top-brass positions that include an undersheriff, a captain, a lieutenant and two administrative roles including an evidence room clerk. A patrol deputy position has also not been backfilled, the DCSO confirmed.
Yet having gaps in top positions comes with its own operational costs.
A captain position, previously occupied by William Bailey since July 2022, has been unoccupied since August 2025. That’s when then-Sheriff van der Kamp placed Bailey on paid leave pending an internal investigation. During a guest spot on a La Pine radio show, Bailey spoke critically of van der Kamp after the Deschutes County DA’s Office placed him on the Brady List for lying under oath.
When Rupert began serving as interim sheriff in early August, he resumed that internal investigation into Bailey’s conduct, outsourcing it to a third-party investigator, while Bailey remained on paid administrative leave. The investigation found Bailey in violation of personnel rules. On March 2, his employment was terminated, but not by Rupert — who recused himself from the decision because he’d been a witness in the investigation — but by a county administrator. Bailey has appealed that decision to the BOCC, which on April 22 approved a third-party arbitrator to hear the case, ascertain facts and make a recommendation to the BOCC. That cost will come out of the county’s risk fund.
By not filling Bailey’s Captain position, Rupert has factored in $14,000 of monthly salary savings into his projection for Fiscal Year 2027, the DCSO confirmed.
Yet if Rupert had backfilled the $250,000-year undersheriff position, which Aaron Wells left when he went to the Bend Police Department in October, the new undersheriff could have made an impartial ruling on the investigation into Bailey’s conduct, potentially saving the County thousands of dollars for the third-party arbitration. (DCSO spokesperson Jason Carr told the Source that Rupert would have referred the matter to the county to ensure neutrality even if an undersheriff had been in place.)
Through a representative, Bailey did not reply to the Source’s request for comment.
As the Source previously reported, if Bailey isn’t reinstated to his post with backpay and the termination scrubbed from his record, he has the option to sue DCSO for wrongful termination and other allegations, as other former DCSO employees have done.
Any settlement or compensation Bailey might receive would add to the pile of about $4.6 million the county has issued in payments and litigation fees since 2006. The County has, since 2016, spent an additional $1.06 million in fighting lawsuits filed against DCSO. That brings the grand total of taxpayer money paid out on behalf of DCSO to $5.66 million since 2006. Presently, there are six litigation cases open with the Deschutes County Sheriff’s Office.
The DCSO told the Source that the potential termination of Det. Lt. James “Mac” McLaughlin and the two other DCSO employees, which Sheriff Rupert placed on paid administrative leave on June 5 pending a third-party misconduct investigation, has not factored into projected savings for Fiscal Year 2027. McLaughlin is Rupert’s opponent for Sheriff in the November election.
This article appears in the Source July 2, 2026.
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A review of the proposed budget shows the absence of the agency’s SWAT team (training, equipment, weapons, communications, vehicles). While interim Sheriff Rupert has stated the SWAT team has been suspended and is undergoing additional training it seems clear Rupert has disbanded this team and claimed by doing so he’s saving money. When the team was stood up under Shane Nelson it faced hard opposition from retired Bend PD chief Jim Porter, who oversaw the CERT capability. Porter is an announced supporter of Rupert’s and it would not be unfair to say the current IA situation involving DCSO SWAT is now serving as a trip wire to deprive the agency and community of a much-needed high risk warrant / crisis capability in the fastest growing county in Oregon. Sleight of Hand or just plain campaign politics?
Wow! Who knew?
Savings of $1MIL dollars claimed? The Deschutes County Sheriff’s Office has seen payouts and litigation fees climb to nearly $6 million for lawsuits filed by its employees since 2020. A significant majority were paid out after 2020 due to a wave of high-profile discrimination, retaliation, and wrongful termination lawsuits under former Sheriff Shane Nelson. In addition, DCSO has paid out more than $465,000 for independent, external investigations since 2020.
Overall, the agency has spent a total of $1.1 million on these outside contractors. Succeeding Sheriffs argue that using external investigators provides unbiased results, critics and internal lawsuits—such as a major federal civil rights suit filed by a former captain—offer that these independent investigators are sometimes weaponized to target political rivals or retaliate against whistleblowers within the department.
Former DCSO captain William Bailey may or may not file a lawsuit depending upon the results of the county-ordered second internal investigation which led to his firing; it is also possible one or all three of the deputies recently placed on paid administrative leave as a contracted IA is being conducted could likewise consider litigation; And how much will it cost DCSO for its contracted investigative service in this instance? Specialized police internal affairs and labor investigations are typically quoted on a custom basis after assessing the specific scope of the assignment; So much for saving the taxpayers $1MIL…sorry, but that dog don’t hunt.
And once again interim Sheriff Rupert uses the agency’s official Facebook page to offer a campaign ad masked as a Media Release – that’s what his campaign site is for as the current SOS Elections investigation of a similar filed complaint points out.
When Les Stiles ran for and then became Sheriff of Deschutes County he introduced “Servant Leadership”, a collection of essays compiled and published as a book by Robert Greenleaf. Stiles’ goal was to remake the internal culture of the Sheriff’s Department, and “Servant Leadership” was the antithesis of historical / conventional law enforcement administrative practices and behaviors nationwide. Sadly, Sheriff Stiles had only one full term to begin the process, his second term cut short due to illness.
This was not over twenty years ago. Sheriffs Blanton and Nelson and Vander Kamp swiftly returned to “business as usual”. The first two having been brought up under Sheriffs France, Davidson, and Brown. Vander Kamp, like Rupert, hired when Stiles was Sheriff. The impact on the agency has been duly noted beginning with leadership scandals and resignations (and one arrest) plus successful lawsuits by employees, with six pending and four more possibly on the way.
Interim Sheriff Rupert proclaims he is modeling Servant Leadership as introduced by Stiles. It’s a catchy phrase. It’s a campaign quip. It’s a book on his shelf in the office he holds…for now. But it is not true.
Within months of his appointment the agency is in turmoil (again) and long serving, respected, well-trained deputies are in limbo due to an increasingly glaring and questionable suspension action. The ability to bring a budget under control – something the County officials should have been overseeing when Nelson’s spending first became questionable – is a commendable skill. However it is not leadership and certainly not Servant Leadership in its full context.
“Servanthood, at its most authentic, calls for deep mutuality. This kind of mutuality requires relational trust, where power is not simply exercised responsibly but is also willingly shared. However, true mutuality cannot emerge when power differentials remain unaddressed or hidden beneath gestures of humility. No display of personal virtue can substitute for the structural courage required to redistribute authority.” – The Dark Side of Servant Leadership, David Forney
On May 18, 2020, Stiles sent this email regarding former candidate Scott Schaier’s run for DCSO Sheriff. “All I can say is WOW—he has taken a novel approach that mixes so many metaphors and theory “pieces” that it is priceless. He is truly a product of our current times and values/beliefs. Bottom line—say enough **** with the right words and nothing else matters.”
We have been here before.