From left, Undersheriff Jennifer Olin and Sheriff Derek Osborne. (Provided Photo)

TOMPKINS COUNTY, N.Y. — Tompkins County Sheriff Candidate Derek Osborne has announced that, if elected, SUNY-Cortland police lieutenant Jennifer “Jenn” Olin would become undersheriff. If Osborne wins the election in November, Olin would be poised to become the first female undersheriff in the county’s history.

“The Sheriff’s Office hasn’t had a woman in the sheriff or undersheriff position since it was founded in 1817,” Osborne said in a news release. “I think it’s long overdue.”

Osborne said Olin, who lives in Dryden and is a longtime Tompkins County resident, has the education, experience and energy needed “to help tackle the ambitious goals” he has for the office, a news release said.

After winning the Democratic primary, Osborne will face off against incumbent Ken Lansing and independent candidate Josh Brokaw in the Nov. 6 election.

Olin has been a lieutenant at SUNY-Cortland since 2010 and was previously an officer with the Ithaca Police Department. Osborne said he met Olin while he was a captain at the Tompkins County Sheriff’s Office and was impressed “by the caliber of her background, her experience and her seeking of higher education.”

She has an associate’s degree in criminal justice from Tompkins Cortland Community College, a bachelor’s degree in sociology/anthropology from Wells College, and a master’s degree in criminal justice administration from Keuka College and more than a dozen certifications and awards “for expertise in police response to drug abuse, domestic violence, dealing with emotionally disturbed persons and rape prevention, and for overall professional excellence,” a news release said.

Though Olin said she is content with her current position, she said she was won over by Osborne’s goals for office.

“I’ve lived in Tompkins County most of my life,” she said. “My family lives in this county, my kids go to school here, and I got married here. I feel a sense of duty to provide the best public safety to this community, and to foster an inclusive department for all who work there.”

Read more about the candidates running here. The Ithaca Voice also co-hosted a sheriff candidates forum with WRFI. The audio and transcript from that event is available here.

Featured image by Armitage Photography. 

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.