“Making Powerful People Feel Uncomfortable Is A Good Thing”: Enter Vermont’s High Bailiffs

Two criminal justice reform advocates, now poised to become high bailiffs, are reimagining this odd office to make the case for civilian oversight on law enforcement. 

The movement against mass incarceration has pushed local officials to get more creative, and rethink how they could be using the arrays of their discretionary powers to break punitive conventions. So far this has mostly manifested itself in prosecutors, sheriffs, and judges.

Enter Vermont’s high bailiffs. 

These little-known county officials have limited powers; mainly, they can arrest the sheriff and can step in when a sheriff is incapacitated. This year, though, two proponents of criminal justice reform—Bobby Sand in Windsor County and David Silberman in Addison County (Middlebury)—decided to run for these offices with a stated goal of harnessing its platform for progressive change and promoting civilian oversight over law enforcement. “Could an obscure county position that harkens back to the 18th century provide a path to police oversight and reform in modern times?” the Vermont Digger asked last week.

Sand and Silberman each won contested Democratic primaries last week. In the general election, Sand will face independents Shawn Orr and Matthew Harootunian, according to the state’s provisional candidate list. Silberman will face Republican nominee Ron Holmes, whom he already defeated in the Democratic primary, and independent Michael Elmore. “I look forward to seeing how [they] can push the limits of this position to expand criminal justice reform,” Sarah Fair George, Burlington’s reform-minded prosecutor, wrote on Twitter after the primary results. “I’m all in! Let’s do it! (Whatever it is we can actually do!)”  

I talked to Sand and Silberman on Thursday in a joint interview about what it is that they want to do, and why they think high bailiffs can be relevant to criminal justice reform.

“It’s up to me as an activist, as a person who’s looking to change the system, to use the tools at our disposal to make our society better,” said Silberman, who has long been an advocate for legalizing marijuana and decriminalizing drug possession. He promised to use an “adversarial” approach to hold the sheriff’s department to account, but also continue speaking up on drug policy. “This campaign is a concrete experiment in the popularity of criminal justice reform,” he said, adding it may strengthen his hand in conversations with lawmakers.

Sand, a former chief prosecutor in Windsor County, called his outlook “more collaborative,” but he says he wants to push against sheriffs’ expanded roles and against the “business” model of law enforcement. “I don’t think it’s law enforcement’s fault that we have dumped responses onto them that are not within their wheelhouse,” he said, “but I think it is our collective obligation to figure out how to divest them of that role by creating other appropriate citizen-based responses.”

Sand and Silberman stressed that they are eager to work together but have not coordinated their campaigns or their language. They both said contrasts between their styles and visions were an asset that would enable them to experiment with the office in various ways and, in the longer run, set up different avenues for progressive change.

“Just the act of voting for a civilian in this position that in recent history has been held by law enforcement sends a powerful message,” Silberman said.

The interview has been lightly edited and condensed.

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Daniel Nichanian: You have centered your bids on this idea that law enforcement needs more civilian oversight. That fits as well into the recent nationwide protests. What about Vermont’s context made you focus on a need for oversight and decide to seek office yourself?

David Silberman: Vermont is very white and very small, but we do see police misconduct going unchecked. Vermont’s sheriff’s departments are roughly as accountable as any other states’, meaning the sheriff is elected but it’s typically not a contested election. We need to have that accountability be more structural, rather than just something that every four years comes up for election—maybe he’ll get challenged, and maybe we’ll have the moral persuasion to make them feel bad when they do something bad—because that never works.

So take away positions from law enforcement: The high bailiff was originally intended as an independent check on the sheriff, but has become something different; it’s basically seen as a sheriff in-waiting. I thought here’s an opportunity to take that power back to the people and say, no, we want civilian oversight. Just the act of voting for a civilian in this position that in recent history has been held by law enforcement sends a powerful message and makes people feel uncomfortable. And making powerful people feel uncomfortable is a good thing, always.

Robert Sand: One of the things that’s challenging for me is not overplaying the significance of my run. Historically, if I’m being honest, this is a position that has done almost nothing. The roles are extraordinarily limited. Having said that, even though it’s hard to find the historical record for this, clearly someone thought it was important to have an independent actor who had the authority to arrest the sheriff, who up until the 1940s was the most powerful law enforcement official in the state because we didn’t have the state police. If we extrapolate from that historic rule of the importance of having an independent actor to today, it’s not a huge leap to then say: Since this is a constitutional role that was designed to be an independent actor, there is value in having a contemporary independent actor. That is what appeals to me about the office. 

The Vermont Digger reported on your criticism of law enforcement functioning as a business. What do you have in mind when you fault this focus on contracts and bringing in funds? 

Sand: Philosophically, there are certain functions that I believe ought to be core functions of government, paid for by taxpayers, not privatized. The manifestation of the private or the business aspects for sheriffs in Vermont largely is speed enforcement, that I’m aware of: Towns will contract with sheriffs to do speed enforcement. 

Silberman: Given what we know about how police pull over drivers and how they select Black and brown drivers for pulling over and enforcement at far greater rates than white drivers, and how we know that they pull over people who look poor, because they drive older cars or beat up cars, the sheriff literally is reverse Robin Hooding, taking from the poor and giving it to himself. 

Another area where sheriffs make quite a bit of money is on construction projects, flagging and site security. There are private companies that can do this, it’s not a law enforcement function. And that money goes to fund the operation of the sheriff’s department: He’s able to take those contracts and fund himself in a way that the county does not already fund him, and thus hire more deputies and grow his department.

So, your criticism is that sheriffs are generating functions for themselves. There’s a related debate around the country on the scope of law enforcement, so that they’re no longer the go-to for mental health crises and substance use issues. Seven Days reported on the sheriff of Lamoille County who has taken on a role of transporting and supervising mental health patients. Is there an opportunity here in Vermont to shrink the role of law enforcement along those lines? 

Silberman: I’m a big advocate in Addison County for replacing the police response with a social services response. With homelessness, with the kind of problems that lead to homelessness, the mental health problems, the drug dependency problems, and that translates into vagrancy, police end up having to respond because we don’t have any other agency to respond to it. We don’t sufficiently fund those other agencies. So I’ve advocated for using our tax dollars differently. 

When the sheriff is able to do what he pleases with the money he brings in, that creates both an opportunity and a risk. Within weeks of me announcing my campaign on a reform platform, our sheriff announced that he is planning in early 2021 to hire two social service workers to be inside his department to help respond to those calls. And on the one hand, it’s great that we can send people who are actually trained in dealing with mental health, health crises, and drug abuse, to deal with those problems, rather than police. But that’s not what would happen here: They would be going along with the police. So we’re not taking away that additional trauma, that potential for introducing violence to a volatile situation. And so that creates a political problem: You want to encourage the sheriff to think about new and better ways of responding to these crises that are not law enforcement crises. But you don’t really want the sheriff to be involved at all. 

Sand: I don’t think it’s fair to fault law enforcement for the fact that we’ve outsourced our mental health response to them or that we’ve abdicated our responsibility. But for so many reasons, law enforcement is the wrong entity to respond to people in mental health crises or to respond to addiction issues. I’ve been a longtime believer in the police social work program that partners a social worker with a law enforcement entity, to have that social worker be one of the first responders. But in a perfect world, and perhaps a long-term offshoot of the defund the police movement—I don’t think it’s law enforcement’s fault that we have dumped responses onto them that are not within their wheelhouse, but I think it is our collective obligation to figure out how to divest them of that role by creating other appropriate citizen-based responses.

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Let’s return to the role of the high bailiff, since we’ve talked about many law enforcement arenas in need of upheaval here: How would this position help with those goals?

Silberman: I think it’s entirely possible to carve out a role for high bailiff under existing statutes that is adversarial, where they are to present a different view and challenge the sheriff—not to scandalize and not to overthrow and not to exceed our legal authority in any way, but to be there as a check in the public sphere. One thing that I would hope to do, should I win, is to utilize Vermont’s very open open records law to start digging into the sheriff’s contracts.

Sand: I suspect David’s style and my style are subtly different. I think I am a little bit more, “Start from a more collaborative place and see what changes can be implemented.” I will say, though, that to the extent I had an ultimate vision for the office, if you think historically this has oversight over the most powerful law enforcement entity in the state, I like the high bailiff’s role not just being constrained to review of the sheriff, but instead to be an independent voice for the justice system. How are police generally doing within the county? How’s the DA generally doing within the county? To what extent is this county utilizing appropriate less punitive responses to harm? In its broadest expression, it is civilian involvement in the justice system.

Silberman: The need for criminal justice reform hits every aspect of the system. It hits policing, the courts and prosecutors. We’re very fortunate in Addison County, to have a reform prosecutor. But if you take a look at one county to our south, Rutland County, there is a regressive DA. And in Bennington, there is the DA who sends the most people to jail per capita of every county. 

Sand: Both of whom are Democrats. 

Silberman: That’s right. And that’s a problem. 

It’s interesting that there is this divergence of views between you about just how adversarially to think of the function, to the extent that you are both engaged in an exercise of reimagining an office that has not done very much. 

Sand: What’s really exciting about this is it’s a blank slate. It wouldn’t shock me if there’s further effort down the road to get more progressive-minded folks in this office, but none of those discussions have happened so far.

Silberman: Bobby and I definitely have different personalities and different approaches. But at the end of the day, we are both deep believers in the need to fundamentally reform our criminal justice system. I can’t say enough about Bobby; he has been doing this for decades. But I think it’s good to have different styles. I’m a big believer in the Overton window; I am in Vermont politics known as a person who will lay out some far into the future policies. I’m out there talking about reallocating our police budgets towards social service agencies. I’m talking about decriminalizing drug possession, taking that outside of the realm of the criminal justice system and dealing with it like in Portugal through the public health system. And I’m very loud about those things, so I think my election will demonstrate to other elected officials that negative campaigning of that person as too “soft on crime” doesn’t fly, at least not in Vermont: People realize that this system has gone too far. 

So, David, your point is that your victory would enable you to cite the electability or legitimacy of those positions.

Silberman: This campaign is a concrete experiment in the popularity of criminal justice reform. I want to make these changes happen, and I’m tired of the slow pace of reform. So this is the way to demonstrate that these policies are popular, that the message of police needing to be accountable to the people is deeply popular.

You’ve described some of what you want to do for oversight with the high bailiff’s office within existing parameters. What do you want done by others to bolster the role of the high bailiff?

Silberman: The legislature is starting to look at the role of civilian oversight in law enforcement. We see also at the local level various groups getting together demanding police accountability. I think this is an area where there’s a real opportunity for the high bailiff role to be expanded, and it’s something that I’m talking about with legislators. If we’re going to create this at the county level, well, you have this independently elected county officer. You could put this person to work. We could enshrine in legislation the independent civilian nature of this role, by having the high bailiff be a core part of this county oversight function. 

Sand: What would be a good extra line to build into the enabling legislation to this position? Whether it’s asking the high bailiff to do an annual or biannual report about the state of law enforcement, the state of the criminal justice system, or the extent to which restorative justice (something that I’m very involved in at Vermont Law School) is part of the response within the county. It could be a fairly innocuous one-sentence addition to the enabling statute that creates the legitimacy and the authorization for a high bailiff to play a more engaged civilian oversight role. 

Do you think the position being an elected one is a positive in that it can tie oversight to the general public, or potentially harmful if it helps people with an attitude hostile to oversight?

Silberman: I think this role being independently elected is a positive to the extent that you can get candidates from outside of law enforcement. It’s not for me to say whether the tools we have at our disposal are the ones we should have. It’s up to me as an activist, as a person who’s looking to change the system, to use the tools at our disposal to make our society better. And that’s how I look at this: I can throw my hands up in the air and say it’s a flawed system, but I think we can be much more productive and get to a much better result if we engage within the system and work from inside to make the changes. It takes a lot of effort, and there’s a very real risk of reformers being co-opted by the system and getting in there and getting a taste of power and not pushing. Fortunately, the high bailiff has no power to get a taste of.

Aug. 25: This article has been updated to reflect the independent candidates who have qualified for the November ballot, according to the state’s secretary of state.