St. Mary’s County Sheriff Candidate Forum Recap
Steve Hall, John O’Connor, and Todd Fleenor

CALIFORNIA, Md. – The 2022 St. Mary’s County Sheriff election has been a competitive race thus far, and with election day quickly approaching, each candidate will be trying their best to convince voters that they’re the right choice.

On June 9, 2022, the St. Mary’s Chamber of Commerce held a public forum that included all three candidates that are running for St. Mary’s County Sheriff. This forum was also planned to hold a discussion for the State’s Attorney office, but due to Jaymi Sterling having Covid, that did not take place.

Steve Hall, John O’Connor, and Todd Fleenor were all asked multiple questions, both preliminary and some from the audience in attendance. They covered a multitude of topics ranging from their own personal leadership experience, officer recruitment and retention, a new headquarters for the Sheriff’s office, the relationship between the Maryland State Police and the Sheriff’s office, the local drug issues, and how they plan on keeping high engagement with deputies as Sheriff.

The St. Mary’s County Sheriff’s office has been struggling with staffing for a while. Recruitment and retention was a big talking point during the forum, most topics revolved around the staffing requirements. All three candidates agreed that men and women entering the force needed more reasons to stay. Whether that came with better leadership or bonuses.

O’Connor stated that he would like to improve on the bonuses for people entering the agency. That even included helping deputies with down payments on houses within St. Mary’s.

“When we’re talking about recruiting and retaining qualified employees…we’re behind the times of how we’re doing bonuses,” stated O’Connor. “I’m looking at bonuses that surpass our neighboring agencies, $25,000 for entry level, up to $50,000 for a very qualified lateral applicant…I also want to make sure that we’re bringing deputies to the county, we’re keeping them here and getting them a home. So one of the options that I wanna look at is helping with down payments on homes…But changing the command climate is the ultimate goal, people stay for good leaders.”

Hall agreed with the strengthening of bonuses including housing and even child care. Fleenor believes that strong leadership and the overall climate of the Sheriff’s office will help with recruitment.

They then moved on to the discussion of a new St. Mary’s County Sheriff’s office headquarters. Steve Hall believes that a need for a new headquarters is a high priority. However, even though they would like to see a new headquarters at some point, Fleenor and O’Connor don’t believe that a new headquarters should be a top priority at this moment.

“I support a new headquarters, but not right now. It’s hard to justify and tell the citizens of St. Mary’s that we need a multi million dollar headquarters when there are buildings that are not staffed properly,” stated Fleenor. “We’re not going to be able to accomplish that for a while because we need the manpower. But, I support a new headquarters, but not at this time.”

When discussing the relationship between Maryland State Police and the St. Mary’s County Sheriff’s Office, all candidates agreed that the relationship is important to maintain and that they are more than willing to work with them. However, after Fleenor was done with his answer, he commented on how O’Connor wouldn’t know about the relationship because he never worked in the county.

“I’m very aware of the relationship, I’ve spoken with the barrack commanders, I’ve spoken with the former majors that were responsible for the area, I even met with the superintendent of State Police,” stated O’Connor. “When it comes guys and gals out on the road, they work amazing together, so I’m very familiar with what happens up at the top end because I’ve had to go all the way to the superintendent and have a conversation with them about that relationship to make sure that officer safety was paramount and that they could talk to each other.”

The next topic revolved around the rising number of overdoses, especially caused by Fentanyl use. Fleenor supports the strengthening of the K-9 unit, and even proposed the idea of starting a crisis response team similar to Calvert County’s. Steve Hall believes in putting more man power into the narcotics team, and John O’Connor explained how the issue is stopping the drugs from coming into the county.

“All of this sounds great, but we can’t do anything until we have the manpower to make it happen,” says O’Connor. “They’re not making the Fentanyl here, it’s coming from someplace else, it’s coming from Baltimore, it’s coming down the road from Prince George’s County. So you have to stop it before it gets here. But there’s also the recovery programs and the mental health services that go along with it, and we need to also work more with the health department. But ultimately we need to stop making independent task forces, we need to work together with neighboring counties to stop the issues before it becomes a problem.”

All three candidates were then asked how they will keep engagement with their deputies when they become Sheriff. Fleenor expressed how he plans on working heavily with deputies and making sure he is doing all the work that he can.

“I’m not afraid of night work, I’ll go out with the deputies, I’ll go out on the streets. Like I said before, I can tell you the name of the roads and streets, I’ve been there, I’ve done it, and it’s only been a short amount of time. I believe the best way to interact and get the feel and pulse of the agency is being one of those people. I don’t consider myself an administrator, I consider myself a rank and file guy who has leadership, supervision, and that somebody can come to me and tell me what is wrong in their opinion without being afraid of repercussions. I agree with O’Connor, you have to have a voice, and I’m that type of leader.”

Steve Hall also had an interesting take on this topic.

“Unfortunately as an administrator, you have to spend a lot of time behind the desk, It’s just a part of the job. I will, as I always have, spend time with the individuals, going to roll calls, checking in. But if you just go out, and you talk directly to the rank and file, you will probably…not wanting to, have absolutely cut your supervision at the knee,” stated Hall. “They are now insignificant, and they have an immediate line to the Sheriff. Your Sergeants, your Senior Corporals, your Lieutenants, you’ve cut them at the knee. You have to empower your supervisors to talk to their people, know their people, and forward the information back up the chain. If you don’t do that, you will set yourself up for a huge failure.”

Later, Steve Hall commented on a topic that was not discussed during the forum, which is school safety. After the tragedy in Texas, many people have been wondering what our local politicians plan on doing to keep our schools safe.

“The one thing that I’m concerned the most about, is the lack of School Resource Officers. Currently, they’re under my command and they do a great job, but there’s seven of them,” Hall told “Lower level schools are visited when they’re on overtime or when they can, so we struggle to make sure that there’s coverage there all the time when schools are in session. So one of my plans is to increase the SRO program to include Elementary schools. I think they’ve done a really good job of hardening the buildings, with security and things of that nature, but we definitely need that oversight and that’s part of my program. Now there’s nineteen elementary schools, so we need the staffing. But that’s something I would like to address soon after the election.”

As July 19th gets closer, It’s really important that we are well educated on the problems that need to be addressed and how these candidates plan on addressing them. All candidates made sure that they’re views were put out there, and with this forum in the rearview, hopefully voters have a better understanding on where they stand.

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  1. Why is Hall holding a rally with so called “constitutional” sheriffs? Does he perceive himself as the sole arbitrator of what laws to enforce? We need a sheriff who will do the things discussed at this forum, not someone who’s going to grandstand and defy civilian input. For this reason I can’t vote for him.

  2. It’d be nice if one would come out and stand against the illegal use of surveillance devices against people by their “Southern Maryland Task Farce” a program using tens of millions of dollars a year to “not catch drug dealers”

  3. Of course the S.A. candidates were suppose to debate. Seems Sterling to too busy being a ball girl at an Orioles game or supposedly catching covid.

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