After five years of running the Annapolis Police Department, Chief Ed Jackson has realized that, perhaps, his position has become something he hoped to avoid: political.

On Nov. 4, 2025, voters will replace Mayor Gavin Buckley, the term-limited Democrat who brought Jackson to Annapolis in 2019. So far, only two candidates have entered the mayoral race, and while both have praised his tenure, only one has committed to retaining him.

In an interview Wednesday, Jackson said he is “at peace” with the possibility of being removed, saying it is “just how the game is played.”

“I’m grateful that I survived five years, and I look forward to continuing the work,” Jackson said.

Much of Jackson’s command staff followed him to Annapolis from the Baltimore Police Department, where Jackson served as a colonel. That fact, combined with assorted other issues, have made for a contentious relationship between Jackson and the officers’ union since July.

The rank-and-file’s frustrations became public knowledge after Jackson suspended two officers earlier this year. The union described the officers as “whistleblowers” reporting waste and mismanagement, and soon issued a vote of no confidence against him. Jackson called “a lot” of the resistance racist — an accusation the union denies.

Jackson, the second Black person to serve as chief of police in Annapolis, said while he wants union leadership to like him, with the mayor’s support, he doesn’t “need them to.”

Both officers were reinstated after a review found no “clear breach of internal policy,” though relations have not improved.

In a statement Tuesday, union spokesperson Jonathan Williams said the United Food & Commercial Workers Local 400 was “disappointed” their concerns have been “ignored,” despite officers demonstrating “overwhelming dissatisfaction” with Jackson’s leadership.

“It is for these reasons that we are disheartened that Chief Jackson has even reached a five-year mark with our department,” Williams said. “We remain committed to holding leadership accountable and working to restore trust and confidence in our department.”

When asked what kinds of things the officers would like to see from their leaders, be it Jackson or a future appointee, Williams declined to comment.

Jackson remains hopeful that he and Local 400 can reach some kind of accord, saying he has been trying to schedule a “sit down” for months.

“They haven’t rejected us. They haven’t accepted it either,” Jackson said. “We just haven’t heard back.”

It is unclear how, or if, the union’s opposition to Jackson will affect his careeronce the mayor’s term ends.

As of Sunday, only two candidates have entered the race to replace Buckley: Ward 3 Alderwoman Rhonda Pindell-Charles and former Ward 5 Alderman Jared Littmann.

Pindell-Charles, who chairs the City Council’s Public Safety Committee, has pledged to keep Buckley’s department heads in place, in the interest of “continuity of government.”

But Littmann said it was “far too early” to commit to keeping Jackson. He said if elected, he would interview the current directors and “determine if there is alignment” between them.

“Making our communities safer is no easy task,” Littmann said in a statement Thursday. “It requires a long-term vision, combined with new, innovative, and thoughtful strategies.”

Outside of government, Jackson’s leadership has been praised by community and civil rights leaders. Shortly before the union’s vote of no confidence, the Caucus of African American Leaders, which includes advocates from several organizations, issued a rare endorsement of the police department.

Caucus convenor Carl Snowden applauded the department’s commitment to diversity throughout Jackson’s administration. Black police officers were not hired in Annapolis until 1960, nearly 100 years after the agency was formed, and under the current chief, Snowden said, diversity has played “a significant role” in building trust across different neighborhoods.

In an interview Wednesday, Snowden said one way that trust has manifested itself is with a gun give-back program city police launched earlier this year. In two separate, voluntary events, the department received 69 firearms, nearly 11,000 rounds of ammunition and even a grenade.

Snowden said the lack of a financial incentive for returning firearms “speaks volumes” to the faith people feel in Jackson.

Civil rights activists have also supported the chief’s commitment to community-oriented policing, an approach that takes social ills, such as mental health, addiction and poverty, into account when responding to crime.

Jackson explored the idea in both his undergraduate and master’s studies at Coppin State and Johns Hopkins universities, respectively.

Many, he said, think about choice as a binary thing, swayed by either an angel or a devil on one’s shoulders. But, Jackson asks, “Why would you have peace” in a place with mold on the walls or without food?

“Crime can be explained,” he said.

One of the department’s most noteworthy outreach tools is a re-entry program that prepares people for life after prison.

The concept is one he adapted from his time in Baltimore — the program’s lead coordinator, Officer Robert Horne, is also from the city. The Positive Impact Program allows participants to explore careers like HVAC training or automotive work or to get connected with drug and alcohol treatment.

Having provided resources to more than 150 transitioning citizens since 2020, Jackson called the program a “point of pride.”

“That’s crime prevention,” Jackson said. “It’s not McGruff dogs and doing TV commercials saying, ‘Take a bite out of crime’ or ‘Just say no’ to drugs. It’s far more complicated than that.”

Despite the chief’s goals and philosophies, the department has made some missteps over the last several years, such as when a woman in crisis was charged with a felony after spending the night in City Hall. Community trust has also been tested by a 2022 data breach that compromised two sources in a murder case, and the 2023 conviction of an officer who ignored several rape and sexual abuse cases.

But Jackson has maintained the confidence of leaders and at least a level of respect from residents. Often, when he is walking around Annapolis people will approach him and start a conversation, even when he is out of uniform.

Jackson hopes to continue building those kinds of relationships through the rest of Buckley’s term.

Another point of focus over the next 11 months, Jackson said, will be strengthening the city’s partnerships with federal law enforcement agencies, including the FBI, the Bureau of Alcohol, Tobacco, Firearms and Explosives and the United States Marshals Service.

To this point, those relationships have brought training opportunities to Annapolis officers and success with some of their long-term investigations.

Those efforts were on display in October, when a swarm of law enforcement agencies raided multiple neighborhoods across Annapolis. The early-morning sting, preceded by a 17-month investigation, led to 11 arrests involving an alleged “open-air drug shop” in the New Vernon and Clay Street neighborhood.

“That’s exactly the kind of thing the department is aware of, but can’t necessarily do on its own very well,” Jackson said.

Have a news tip? Contact Luke Parker at lparker@baltsun.com, 410-725-6214, or on X @lparkernews.