Jillian Hanlon’s bid for Dutchess County Sheriff would make her the first openly transgender sheriff in the United States.
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Jillian Hanlon, a recently retired Dutchess County deputy sheriff, announced her bid for Dutchess County Sheriff earlier this year. If elected, Hanlon will make history as the first openly transgender sheriff in the United States.
Unanimously endorsed by the Dutchess County Democratic Committee, Hanlon is running against Acting Sheriff Kirk Imperati, a Republican who filled the position last September following the death of Sheriff Adrian “Butch” Anderson.
As an over two-decade veteran of the department, Hanlon says she has the experience and ideas to best serve the community as Dutchess County Sheriff. Recently, Examiner+ connected with Hanlon to discuss her motivation for running, her vision for just, compassion-informed policing, and what it would feel like to make history if elected.
Examiner+: Can you tell me about your background and how it positions you well for the position of sheriff?
Jillian Hanlon: I have more than 37 years of total experience in all aspects of public safety, including EMS, fire, and infrastructure protection. For the last 24 out of 25 years, I’ve been with the Dutchess County Sheriff’s Office.
I was a corrections officer in the late 1990s for two years. In 1999, I was selected to be a deputy, and I went to the Kingston Police Academy. I was elected class president and graduated with top academic honors.
Since then, I’ve had an amazing career. For most of my career, I was a school resource officer. I did that, community policing, and juvenile aid. I also was the public information officer for 12 years.
I’ve developed a number of durable programs, including co-founding the Dutchess County Law Enforcement Critical Incident Response Team. I also assisted in the development of the Juvenile Firesetter program, which is a non-punitive juvenile firesetter intervention response and education program. I helped bring nasal Narcan to Dutchess County and was the one who trained all the staff on it. That saved hundreds of lives here.
Most recently, I was with the Justice and Transition Center team. We’re building a brand new state-of-the-art correctional facility. The focus is going to be on rehabilitation and not punishment. I had such an amazing opportunity to contribute to that project — from the design of the facility to developing the staffing plans, policies, and procedures. While I was doing budgetary analysis, I realized we could save anywhere between $800,000 and $1.2 million on the cost of the kitchen equipment. It was my analysis that the country relied on when awarding the security contact [for the facility].
I have an incredible breadth of experience. I’ve spent time in the trenches and in the boardrooms. I’m uniquely positioned to lead the sheriff’s office into the new century.
Examiner+: If elected, you’d like to focus on just policing and compassion. Can you tell me more about how these ideas would influence your leadership and decision-making?
Hanlon: The sheriff has three primary responsibilities. What we often think of with the sheriff is the part people see the most: the deputies on patrol. But there are two other things that we do that are very important. One is civil process, so enforcing court orders and serving papers for the court. The third thing is we maintain the jail.
That’s one of the largest parts of the entire county budget, and right now it’s a black box. I talk a lot about compassion, and here’s a perfect example of where a lack of compassion leads to a corrupt outcome. We have to provide the inmates with prepared food, but nowhere does it say that the food has to be palatable. What ends up happening is the vendor cheaps out, and the food the inmates are given to eat is inedible. It smells bad, it doesn’t look like food, and it doesn’t have a decent texture. It’s oftentimes cold, and sometimes it doesn’t even look like food.
What does that do to you as a human being? Where are you going to get the calories that you need in order to survive? Conveniently, the same company that provides the breakfast, lunch, and dinner also provides the commissary. So by punishing inmates and giving them crappy food, we’re actually allowing a huge corporation, Aramark, to drive sales of potato chips and peanut butter. We’re encouraging a company that has no problem making a profit to use the most vulnerable among us and exploit them.
I think that’s immoral and also an officer safety problem because everyone knows what it’s like to be hungry. It punishes those who don’t have enough money and creates an underground economy in the jail because you have haves and have-nots.
My focus on just policing isn’t about rainbows and unicorns. It’s about digging deep into the gritty problems that are at the root of crime and disorder. If we treat people like animals on the inside, how can we expect them to behave differently when we’ve released them? Clearly, crappy food has been completely unsuccessful in discouraging people from ending up in jail because we have the same recidivism problems. They come back because of poverty, desperation, lack of opportunities, trauma, and opportunistic crimes.
There are some really esoteric beliefs that if we are extra cruel to our prisoners and teach them a lesson, they’ll never come back to jail. What [that idea] does instead is creates hardened criminals who are more likely to assault both correctional staff as well as law enforcement officers in the field.
If we want to serve the aims of justice, it’s really important that we look out for the most vulnerable, even those who have committed crimes. The goal is to get them to not commit crimes in the future, not to make them hungry, angry, frustrated, and more likely to lash out.
Hanlon: Honestly, it’s the jail. I only worked there for 2.5 years and had three years with the Justice and Transition Center. There are really good people who work in the jail, and they deserve to be treated better.
We have people in the jail who are very troubled, who we then release in a worse condition than they came in. Then we wonder why there’s a crime issue.
We know what the causes of crime and disorder are, and giving inmates crappy food just to pad the pockets of a very large corporation and punish people while, at the same time, creating all sorts of security problems, is not effective. It’s not a wise use of our resources, and it also shocks the conscience.
I’ve arrested parents who have used food as punishment for their children. We should not be doing that to inmates, regardless of what they’re accused or convicted of.
I also think we need to get a hold on the overtime. The Republicans have controlled the county legislature and the Sheriff’s Office since close to the beginning of time in Dutchess County. They have consistently refused to pay a salary that will recruit and retain staff, and they refuse to correct serious organizational toxicity in the jail. It’s going to lead to either a huge lawsuit or the loss of life someday. I think both the jail staff and inmates deserve better.
Examiner+: Aside from helping to reform the jail, are there any specific departmental issues you’d want to address?
Hanlon: We’ve done an amazing job at providing police services in Dutchess County, and I like to take a little bit of ownership of that because I was a long-time trainer.
What I’d like to do is continue to improve training. Right now, we are considered the premier training agency, but we end up losing staff to other departments after we train them. That’s not right. It’s a waste of Dutchess County taxpayer dollars and talent. We should be able to pay our deputies enough to recruit and retain them.
I’d also like to see more acceptance of queer people. I’m the very first out trans person in the Dutchess County government — not just the Sheriff’s Office. We’re still behind the times.
I’d like to focus on ensuring that officers have access to effective and compassionate mental health services. [Officers] deal with other people’s suffering, gore, and death, and it really takes a toll. When you have officers who are confident enough to be able to ask for help when they’re struggling, you don’t have officers who make bad judgment calls or end up hurting themselves. I’m not sure the acting sheriff or previous administration did much more than lip service for that.
Examiner+: If elected, you’d be the first openly trans person to occupy the role of sheriff in the whole country. How does that feel?
Hanlon: It’s humbling. It’s an amazing honor to be able to the first person to occupy that role.
I have a tough fight ahead of me, but it’s a winnable fight. I have to inspire people that there’s a better way for us to police.
Examiner+: What would representation for the broader LGBTQ+ community in Dutchess County mean to you?
Hanlon: In Dutchess County and the Hudson Valley, there are so many kids who are growing up gay, lesbian, bi, trans, and nonbinary. It’s hard to grow up on a good day. When you have all the complications of being part of a group that society has spent the better part of the last 2,000 years beating up on, it’s even harder and can be very discouraging.
We talk about the high levels of suicide and suicide attempts among trans youth. The reason for that is desperation. If you’re hopeless and people have been telling you that you’re worthless, you are at a huge risk of self-harm, including terminal self-harm.
I think my taking this position, coming out in a politically conservative, hyper-partisan political environment, going through the challenges I had, overcoming them, and maintaining the respect of my coworkers while doing it is an amazing story for kids. Maybe they’ll see me, and it’ll inspire them to make history themselves.
Examiner+: Come Election Day, why should voters support you?
Hanlon: The voters have a very clear choice. They can always do what they’ve always done and get what they’ve always gotten. Or we can move policing into a new century where we focus on the root causes of crime and disorder, where we help people avoid committing crimes rather than create situations where they’re almost compelled to.
I think a vote for me is a vote to reach across the aisle. It’s to say that, yes, conservatives have important concerns that need to be heard. At the same time, we cannot punish innocent people.
I had an opportunity to meet with a group of people who had some very far-right leanings to ask them for their vote. There was one gentleman there who wanted to know about masks and vaccine mandates and where I stood on those. I said when you’re in public, it’s important to protect other people. While you might have an absolute right not to get vaccinated, you really should be wearing a mask in public because there’s no informed consent, and we must protect the vulnerable.
He wanted to know how I felt about inmates having access to law libraries so they could “file frivolous lawsuits all day.” I said that they should have access to it. Just because they’re not going to be able to pass the bar that doesn’t mean that they’re not learning valuable skills. Maybe it’ll open up doors for them in the future. If they’re [in jail] because of police or prosecutorial misconduct, they better have that access to fix what went wrong.
He had another question about the police seizing property and using it for themselves. I discussed how searches and seizures go and our role in asset forfeiture. He was the one who had the hardest questions for me out of all of them, and yet he was the one who told me that I earned his vote.
I think a lot of the polarization this country has is manufactured. We can reach across the aisle. We can connect with those people that we wouldn’t normally connect with because we all share common values.
We all want to be safe. We want our kids to be safe and thrive. It’s really important for us to be able to grow together as a community despite our differences and be able to listen to each other. I think that’s what separates me from my opponent.
Bailey Hosfelt is a full-time reporter at Examiner Media, with a special interest in LGBTQ+ issues and the environment. Originally from Connecticut and raised in West Virginia, the maternal side of their family has roots in Rye. Prior to Examiner, Bailey contributed to City Limits, where they wrote about healthcare and climate change. Bailey graduated from Fordham University with a bachelor’s in journalism and currently resides in Brooklyn with their girlfriend and two cats, Lieutenant Governor and Hilma. When they’re not reporting, Bailey can be found picking up free books off the street, shooting film photography, and scouring neighborhood thrift stores for the next best find. You can follow Bailey on Twitter at @baileyhosfelt.
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