Updated 6:07 p.m.

Three young teenagers fatally shot a 65-year-old man while he collected cans along a quiet North Portland street and then took his car on an hours-long joyride through St. Johns that included a stop at Taco Bell, prosecutors alleged Friday.

Eugene Woodruff, 14, was the first to appear in Juvenile Court and sobbed as the family of the man he’s accused of killing described their loss.

Woodruff can’t be tried as an adult because of his age and was ordered held in the Donald E. Long Juvenile Detention Center until his next hearing Nov. 8.

Aaron Lewis Criswell and Richard Jerome Rand, both 15, were arraigned later on first-degree murder with a firearm and multiple other charges under Oregon’s Measure 11 mandatory sentencing law. They will be tried in adult court.

Prosecutors said at least two of the boys knew Ricky Malone Sr., who was found dead Oct. 14 from a single shotgun blast to the chest at close range.

A blood-soaked paper bag filled with beverage containers was found beside his body early that morning in the 10200 block of North Mohawk Avenue, according to police and court records.

Malone’s family, invited by prosecutor Eric Zimmerman to address the court, expressed shock, disbelief and heartbreak as each teen entered to hear the charges read against them.

“He was canning. Was that a crime?” said Donnece Malone White, the victim’s sister, during Woodruff’s brief appearance.

The long-haired boy, wearing the green t-shirt and khakis issued to juvenile defendants, hung his head and tried to fight back tears.

Robert Malone later spoke of his younger brother’s children and grandchildren as well as his lifelong ties to the St. Johns neighborhood. All the while, Criswell cried.

“Not only did I lose a brother, but I lost a best friend,” Robert Malone said.

Prosecutors said it all began with a botched home break-in planned at Woodruff’s house.

Armed with a 12-gauge shotgun and wearing Halloween masks, including that of a clown, the teens first set out to rob a house in the 10200 block of North Midway Avenue around 3:45 a.m. but were scared away by someone living there, according to a probable cause affidavit.

They then walked a mile over to North Mohawk Avenue and ran into Malone, court documents show. The teens said they knew Malone from the neighborhood.

Criswell, who told police his brother dated Malone’s daughter, pointed the shotgun at the can collector and demanded he let them take his blue Toyota Avalon, which was idling nearby, prosecutors allege.

The teen fired one round into Malone after he refused, according to the affidavit.

Rand hopped into Malone’s Toyota and the three teens spent the next few hours cruising about the neighborhood before ditching the stolen car, according to prosecutors.

During the suspected joyride, police received multiple hit-and-run reports around the neighborhood that included the same car, authorities said. One caller got the license plate, which matched Malone’s car, prosecutors said.

At one point, around 7:30 a.m., the three teens stopped for a bite to eat at a Taco Bell drive-thru with Woodruff behind the wheel, which was captured on video. A receipt for the fast-food run was left inside Malone’s car, which police recovered in the 8500 block of North Hodge Avenue, prosecutors said.

A homeowner on North Allegheny Avenue, just several blocks from the shooting, later found the shotgun in some of his shrubs, court documents stated.

Police on Thursday arrested the three teens after serving a warrant at one of their homes.

In addition to the first-degree murder charge, Criswell and Rand face two counts of second-degree murder with a firearm, first-degree robbery with a firearm, unauthorized use of a vehicle with a firearm and first-degree burglary with a firearm.

They are scheduled to return to court Nov. 1.

Woodruff faces a murder charge.

Outside the juvenile detention center, Robert Malone thanked the Portland police, St. Johns residents and others for helping with the case.

“All and all, the community — the churches — did a heck of a job in holding us all together,” he said. “But we’ve got a long road to go.”

Ricky Malone’s family has set up a GoFundMe account to help with financial costs. You can donate here.

-- Shane Dixon Kavanaugh; 503-294-7632

Email at skavanaugh@oregonian.com

Follow on Twitter @shanedkavanaugh

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