Derek Osborne. (Provided Photo)

Derek Osborne is facing off against Ken Lansing in the democratic primary Sept. 13. Ahead of the primary, The Ithaca Voice and WRFI are hosting a live candidates forum with Osborne, Lansing and independent candidate Josh Brokaw. To learn more click here and to submit a question for the forum, click here.

TOMPKINS COUNTY, N.Y. — Former Tompkins County Undersheriff Derek Osborne was born and raised in Cortland, and that is where he started his career in law enforcement. He worked for the Cortland Police Department for six years and transferred to the Tompkins County Sheriff’s Office as a road patrol deputy in 2001.

Derek Osborne. (Provided Photo)

At that time he moved to Freeville, but now lives in Lansing. After working as a road patrol deputy for a couple years. From there, he was promoted to investigator, then senior investigator, then captain and finally undersheriff under Sheriff Ken Lansing around 2011. He was undersheriff for four years until he retired in 2015.

After retiring, he worked with federal inmates in Syracuse pending release taking part in community reintegration efforts. He currently works at CFCU.

Why is he running for sheriff?

He said he has never had the opportunity to shine and take that last step.

“Honestly, I didn’t have an intention of running when I left or for quite some time, I just haven’t liked what I’ve been seeing the last few years,” Osborne said. “The budget overruns, the personnel issues, and some of the things the sheriff has said publicly have been very concerning to me. I just feel like a sheriff can do more than what’s being done now and I believe the sheriff’s office can do more for the community than what’s happening now, so I want to change that.”

Osborne is critical of Lansing and said one of the biggest things that concerned him regarding the current administration was an interview Lansing had with former Ithaca Voice editor and founder Jeff Stein, during which Lansing talked about a conspiracy of powerful people in the county to see him ousted from political office.

Osborne also said he doesn’t feel like “(Lansing’s) heart’s in it. I feel like he was somewhat absent for a number of years and then all of a sudden now the election is around, and now of all a sudden he’s trying to gain all this support.”

In 2015 after retiring, Osborne wrote a nine-page letter accusing Lansing of providing misleading information about the Hornbrook Road incident in Danby. In December 2014, there was a 61-hour standoff on Hornbrook Road in Danby. Police were attempting to apprehend resident David Cady on a DWI warrant. During the incident, the home was destroyed and Cady ultimately died of a self-inflicted injury. In the letters, Osborne was critical of Lansing not being reachable at the onset the incident and for blaming Osborne. Read the letter as well as response from Lansing at the time here.

Osborne said he didn’t want to sit back and see Lansing run unopposed again.

Why did he retire from the Tompkins County Sheriff’s Office?

Osborne retired after 20 years at the sheriff’s office. He said he was too opposite from Lansing and it was a good time to go.

“I didn’t like or appreciate his leadership, or lack of leadership, and it was just my time,” Osborne said. “I felt like I just couldn’t tolerate it anymore. I felt like the longer I was there, the more I was a part of it.”

What is Osborne’s platform?

The key issues Osborne lists on his website are honor, pride & integrity, community engagement, diversity, the drug epidemic, fiscal responsibility, crime response and corrections.

Having stepped outside law enforcement, Osborne said he now has a citizen’s perspective of law enforcement. Osborne said based on a criminal justice and jail study published in 2017, many people in the community feel disengaged from the sheriff’s office.

“If a relationship does exist, they feel like it’s the community actually the one pushing it, not the sheriff’s office,” Osborne said. “That really hurt. It was easy to say, ‘yeah I’m not there any longer’ but that’s not what the sheriff’s office should be about. If I was the sheriff, I would really take those statements to heart and I would be proactively trying to change that. I haven’t seen that happening. I haven’t seen any changes since those comment came out.”

Osborne said if he was sheriff, he would be asking what he is going to do to turn this around. He said he likes some of the community-building initiatives the Ithaca Police Department has taken like coffee with the chief. He also said deputies should have more of a presence in the community and take the time to meet and talk with people.

“In my campaign, going door to door and talking to people, I was surprised at the number of people who didn’t even know who the sheriff was,” Osborne said.

One of the biggest concerns Osborne said he has heard from people while campaigning is about traffic enforcement and speeding in their neighborhoods.

Another key issue Osborne said is to increase diversity in the sheriff’s office, which will involve encourage more people to take the civil service exam and make people interested in pursuing a career in law enforcement. He acknowledged the challenge in doing that when many people have only had negative experiences with law enforcement.

How will he balance the budget?

“It’s all about managing your resources, which is the people,” Osborne said. “Overtime was at a historic low while I was there and it wasn’t because I was managing the budget and the money and the overtime itself, I was managing the people. If you manage the people and know how they work, the overtime and the budget takes care of itself. It’s not rocket science.”

What is his stance on reducing jail population and alternatives to incarceration?

He said working in re-entry in Syracuse after retiring from the Tompkins County Sheriff’s Office opened his eyes to another aspect of law enforcement.

“I spent a whole career arresting people and I’m not going to deny that there were a lot of times that I had a lot of fun doing that, I mean especially when it’s somebody that has done something horribly wrong. You want to apprehend them and make them pay, you want to do it for the victims,” Osborne said. “But working in Syracuse made me realize there’s a whole other gamut to the criminal justice system that I wasn’t really seeing or focusing on. Yeah, there’s a time and place for enforcement, arresting people, that’s all fine and good. … But if we’re not helping these people be more productive citizens, we’re really not solving anything. They’re just going through the cycle and we arrest them again a month later.”

Osborne said one time at the Tompkins County Jail, he realized a father and son were incarcerated at the same time.

“That really strikes you,” he said. “Now I’ve incarcerated two generations of a family. What is not happening to stop this? I don’t think it makes you a weak law enforcement person if you’re concerned about recidivism. I think it makes you more well-rounded.”

What should the sheriff’s role be in the community?

Osborne said being sheriff requires being a leader and mentor, and a person in the community that people trust.

“You have to be that person the community trusts and knows that if something happens you’re going to be there, knows if they have an issue or concern, they’re comfortable and they trust you enough to reach out to you or your department to report it,” Osborne said. “I’ve heard a lot of that from certain segments of the community that they will not call the police and that’s really sad.”

Why does he think people should vote for him?

“Honestly, if I’m lucky enough to get in this position, I’m going to give 120 percent. I want the community to know that. I want to make the sheriff’s office something everybody is proud of in this community and that’s my goal. And I will do it,” Osborne said.

Endorsements: Peter Stein, former Tompkins County legislator; Gwen Wilkinson, past Tompkins County district attorney; Cathy Valentino, past Ithaca Town supervisor; Legislature Chair Martha Robertson and Tompkins County Progressives.

More Information: Visit

Kelsey O'Connor

Kelsey O'Connor is the managing editor for the Ithaca Voice. Questions? Story tips? Contact her at and follow her on Twitter @bykelseyoconnor.