For more than two months after their relationship ended, a Portland police officer tormented a fellow officer and used police resources to try to track who she was associating with after hours.

Last year, Jonathan Lackee pleaded guilty to domestic violence stalking. A police investigation found he sent the victim repeated, intrusive messages after she had told him to stop. Once she reported his behavior, Lackee was placed on leave and the case played out quietly in court for months.

Lackee’s prosecution offers a window into how a department investigated and pressed charges against one of its own, starting a process often shrouded from view because of confidentiality laws and legal gag-orders. The criminal complaint offers the only public record of what happened.

In an affidavit, a Portland police detective described how Lackee’s aggressive behavior and persistent messages reached a peak late one night when the target of the harassment believed Lackee, a K9 officer, was following her in his cruiser as she returned home. He sent her message after message implying that he was watching her.

Jonathan Lackee and his K9 dog Dozer Photo from Portland Police Department website

“What are you up to?”

“Sure you’re not talking to anyone?”

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“I don’t know why you lie to me about it. Telling me the truth would make it easier.”

“You aren’t seeing anyone? So where were you last night over night?”

Lackee was charged in April 2020 and pleaded guilty in August 2021. But the case may be dismissed as part of a plea agreement known as a deferred disposition. If a judge finds that he followed the conditions of his bail that forbid him to contact the victim or enter Portland except for certain appointments, the misdemeanor charge could be dismissed at a hearing Feb. 11.

After the co-worker he was stalking reported his behavior, the police department placed Lackee on paid administrative leave from mid-August 2019 until he negotiated a deal to resign in December 2020. As part of the separation agreement, the city paid him $40,000 – and in exchange, Lackee agreed not to sue the city. Portland promised not to publicly disclose the circumstances of his departure or inform the Maine Criminal Justice Academy, which licenses officers statewide, about the allegations because Lackee disputed them.

By law, police chiefs must tell the academy about certain types of police criminal conduct or convictions. Portland police notified the trustees in January 2021, after Lackee’s guilty plea; Lackee agreed to surrender his license to work as an officer, ending his municipal law enforcement career in Maine.

Lackee’s criminal attorney, Matt Nichols, did not return a call and an email seeking an interview. The city of Portland also declined to answer questions about the case. Lackee referred questions to his employment attorney, Jonathan Goodman, who declined an interview but confirmed basic time-line information, including Lackee’s paid leave.

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The severance agreement permits the city to confirm only the dates of his employment between 2013 and 2020. It also allowed Lackee to keep his police dog, Dozer.

“This agreement is not intended to be, and shall never be treated as an admission of wrongdoing or liability or responsibility by any party at any time or in any manner whatsoever,” it reads.

The $40,000 payment included wages, accruals, vacation, sick leave, personal time, holiday hours, comp time and one month of transitionary health insurance, according to the contract, which the Press Herald obtained through a public records request.

The female officer reported Lackee in August 2019 after two and half months of escalating harassment in which he repeatedly texted, emailed and contacted her after she had told him to stop and warned that she would report him.

The harassment had begun that June after Lackee’s relationship with the woman ended, wrote Portland police Sgt. Dean Goodale in an affidavit for Lackee’s arrest filed in court. The female officer provided Portland police with a cache of digital records documenting his unwanted communications, some of which Goodale cited in the court records.

“Lackee repeatedly called and/or texted her while she was at work,” Goodale wrote. “She continually asked him to stop and said Lackee’s messages became angry or paranoid if she did not immediately respond to him.”

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The Portland Press Herald/Maine Sunday Telegram does not name victims of abuse without their consent. Lackee’s victim declined an interview request. But the arrest affidavit describes how over more than two months, Lackee intimidated and harassed her, intruding on her life and work and undermining her sense of safety.

His messages flip-flopped from suspicious and accusatory to pleading and self-pitying.

“I miss you,” he wrote. “I hate myself.” “I want to die.”

After someone he knew liked a photo of her on social media, he made his jealousy clear.

“I’m sure he’s not the only one who’s messaged you but I don’t think you’d tell me and I don’t even care to know,” he wrote in a social media message described in the affidavit. “Sorry it bothers me that 80 guys like everyone of your pictures and some of them I know are thirsty.”

By July, the female officer had changed her daily routine because of Lackee’s anger. Lackee was paranoid about where she was and who she chose to spend time with. She was not eating well, felt sick and stopped exercising, and lost over 20 pounds, the affidavit said. She also began avoiding her family.

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Lackee continued calling her and seemed to be monitoring her movements. In one case when they were both on duty, after the woman finished with a police call, she went to get coffee with a co-worker. He accused her of ignoring his calls while still having time to chat with someone else.

“His apparent knowledge of her whereabouts led (her) to believe that he was tracking her police vehicle,” Goodale wrote.

At the end of July, the woman blocked Lackee on social media because he would not stop messaging her and was “going on an absolute rampage,” she told an investigator.

In his messages to her, Lackee said he did not recognize cars in her driveway, indicating that he was keeping an eye on her Portland apartment. His suspicions were ultimately misplaced. Five other people lived in her apartment building and parked outside.

When she gave police a list of vehicles that normally were parked in the driveway, Portland investigators found that Lackee had used his access to a police database to run the license plate of one of the vehicles in November 2018 and then in August 2019, after they broke up.

That SUV belonged to someone who lived in the building, Goodale wrote.

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Lackee’s conduct continued to intensify in July. He began contacting other people to ask about the victim, and she suspected Lackee was monitoring her movements after work.

Goodale wrote that an internal affairs investigator, Portland police Sgt. Christopher Dyer, interviewed witnesses who had been contacted by Lackee. They described him as “slightly threatening,” “possessive,” “jealous,” “controlling,” and “intimidating,” Goodale wrote.

In one case, on July 31, Lackee somehow knew the female officer had gone out to a restaurant with friends, but he was paranoid that she might be somewhere else.

He sent her a message: “(I don’t know) why you chose to ignore me when all I ask for is a text,” he wrote. “I know you aren’t still at a restaurant because there are none open in Falmouth this late during the week.”

In reality, the female officer was still at the restaurant table talking. The waitstaff had allowed the group to finish their conversation as they cleaned up for the night.

His harassment of her peaked Aug. 13 and 14, 2019,  when she was scared to go home after receiving a barrage of messages from him. She was afraid he would be at her house waiting to confront her.

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“What’re you up to?” he wrote. “Sure you’re not talking to anyone? (I don’t know) why you lie to me about it. Telling me the truth will make it easier. Hope you’re enjoying your night hanging out.”

“You aren’t seeing anyone? So where were you last night over night?”

She waited for hours to go home. When she pulled into her driveway around 3 a.m., she thought she saw a Portland police cruiser – Lackee – following her. She ducked behind bushes as she ran inside.

“I never felt like he’d be physical but that night just made me scared to go home because of how verbally … aggressive he gets and I just hate the way that he is either always mad at me or putting me down or accusing me of stuff,” the female officer told investigators. “So I was afraid if that if I pulled in and he was right there … he’d see me… and he’d either do it in person or he’d send a bunch of emails getting extremely mean and angry at me.”

“It’s really traumatizing the way he yells at me and gets mad at me … and I’m just tired of it, so I didn’t want him to see me coming home.”

The next day, she reported Lackee to supervisors. He was still sending her harassing messages as she met with human resources, according to the affidavit.

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The Portland Police Department started an internal investigation and Lackee spoke to internal investigators twice, according to court records.

What he told investigators during those interviews was excluded as potential evidence in his criminal case, under a legal principle called Garrity protections, which prevents the disclosure to criminal prosecutors of testimony given by public employees during internal investigations.

To force a public employee to answer questions under threat of termination, and then have the government use those words to bring a criminal case, violates the employee’s Fifth Amendment right against self-incrimination, the U.S. Supreme Court held.

After he was charged, Lackee moved to a Bangor suburb and began work as a private security guard, according to court records and his LinkedIn account.

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