A car related to the fatal shooting on Woodford Street in Portland on is loaded onto a flatbed tow truck as a Portland police officer surveys the ground nearby. Gregory Rec/Staff Photographer

Portland police this week charged three men in a fatal April shooting on Woodford Street.

Damion Butterfield, 23, of Saco, was charged with murder in the death of Derald “Darry” Coffin, 43, of Bath, and attempted murder of Annabelle Hartnett, 27, who was wounded but survived.

Thomas M. MacDonald, 44, of Westbrook, and Anthony L. Osborne, 45, of Standish, each face one count of felony murder, court records show.

Derald “Darry” Coffin Photo courtesy of Terry Leonard

Felony murder is a law used to hold people responsible for a homicide that occurred in the course of the commission of another crime, including robbery, even if the defendant did not directly cause the death or pull the trigger.

Hartnett, a witness and victim in the April 26 shooting, told the Portland Press Herald that she believes Osborne was responsible for orchestrating an attempted shakedown and the shooting. She said other than Osborne, there were three people who attacked Coffin, meaning one person could still be at large. Police declined to address her version of events or say whether another suspect could be arrested.

MacDonald was booked at Cumberland County Jail about 9:45 p.m. Wednesday after his arrest at the Portland Police station on Middle Street. Osborne was arrested after 1 a.m. Friday on Parris Street in Bayside. Butterfield had been incarcerated at York County Jail since April 27, the day after the shooting,  on unrelated charges, which include a probation violation.

Butterfield made a brief court appearance via Zoom before Cumberland County Superior Court Justice MaryGay Kennedy, who ordered him held without bail.

Appearances were postponed until June 23 for MacDonald and Osborne, who are being held on $500,000 cash bail. An attorney representing Osborne said he was suffering from the symptoms of drug withdrawal and was not in a position to understand the proceedings against him. It’s unclear why MacDonald’s appearance was postponed.

Police did not authorize the release of booking photos, said David Singer, a police spokesman.

All three men will have to be indicted by a grand jury because they face felony charges.

Osborne was charged with murder once before, in 2000, for the stabbing death of Brandon Feyler, 21, outside Osborne’s apartment on Seavey Street in Westbrook. He pleaded guilty to manslaughter and served 14 years of a 15-year prison sentence. Since his release, he has had multiple convictions for domestic violence and violating a protective order and faced other low-level charges. He was sentenced to serve 2 ½  years in prison for felony-level violation of a protection order in 2020, and it’s not clear when he was last released.

MacDonald has three misdemeanor convictions, the first two from the 1990s. The most recent was a 2021 guilty plea to disorderly conduct.

Butterfield’s record was not available Friday.

Police offered scant information about how they tracked the three men down and connected them to the fatal shooting. A judge impounded an affidavit of probable cause in each arrest. But the court records include a couple details.

The gun that police say Butterfield used was described as a .22 caliber, TA76 Tangfoglio revolver, and its serial number was listed as C03246, suggesting that they recovered the weapon.

Terry Leonard, Coffin’s brother, was happy to hear of the arrests. Police called Friday morning to tell him, he said.

“Now it’s just getting through the court system, I guess,” said Leonard, of Bath. “I’m sure it will be who knows how long.”

Before he was killed, Coffin had spent a couple of days with Hartnett, to whom he’d become close when she began dating his cousin.

In an interview last month, Hartnett gave the Press Herald an account of what happened when she and Coffin met up after midnight on April 26, a short time before the shooting, with a man known to her only as “Bear.” As she and Coffin drove toward Woodford Street with Bear in the car, she said, Bear begged Hartnett and Coffin to give him 5 grams of heroin to resell from an apartment on Cumberland Avenue.

But Hartnett and Coffin told him they did not have anything to give him, that they were struggling themselves. Bear then asked where they were headed, Hartnett told him, and Bear made a phone call and repeated the address to someone else on the line.

A few moments later, as Coffin, Hartnett and Bear sat in Hartnett’s SUV smoking cigarettes outside the apartment building on Woodford Street where Hartnett and Coffin were staying, three men approached the vehicle from behind, pulled Coffin out of the passenger seat and beat him before one of them shot Coffin twice, Hartnett said. She said Bear got out of the SUV and watched the assault, and didn’t appear surprised.

The gunman then tried shooting Hartnett in the head, but the bullet missed her by inches, passing through the brim of her baseball cap and a scarf around her neck. A second round ripped through Hartnett’s upper arm, wounding her. After Coffin and Hartnett were shot and the gunman fled toward Back Cove, Bear asked Hartnett again to give him drugs before the police arrived.

““He kept saying, ‘Give me anything you guys got, because the cops are gonna be here. If you guys have anything on you, give it to me now,’” Hartnett said in an interview after the shooting. “And I was like, ‘Get away.’”

During the interview last month, Hartnett said she’d learned Bear’s real name was Anthony Osborne.

Annabelle Hartnett stands on Woodford Street in Portland near where she was shot and her friend Darry Coffin was killed on April 26. Ben McCanna/Staff Photographer

Hartnett spoke to the Press Herald because she felt police had mistreated her in the immediate aftermath of the shooting. Hartnett and Coffin used drugs, she said, and she has struggled with addiction since she was a young teenager. She felt the police officer who interviewed her, Detective Andrew Hagerty, was callous and unkind, she said, as if her drug use made her unworthy of courtesy and respect.

“Once you have like a record it feels like no matter what, every time I’ve been stopped by the cops like with the way that cop talked to me, Hagerty, after that you’re never a victim, you are always somehow, like, no matter what, you’re just a criminal in their eyes,” Hartnett said.

One day before Hartnett’s story was published and hours after a reporter asked Portland police for an interview about her criticism of Hagerty, police charged her with misdemeanor counts of receiving stolen property and violating the conditions of her release.

She was jailed for 29 days until Thursday, when she accepted a plea agreement that resolved multiple criminal cases against her dating back a year.

During the news conference Friday to announce the arrests, interim Police Chief Heath Gorham praised Hagerty and the other detective on the case, Daniel Townsend.

“You heard the last part of my statement,” Gorham said after a reporter asked whether the police were looking into Hartnett’s allegations of disrespect. “We could not be more proud of the work of Detective Hagerty.”