Worcester to Springfield to Pomfret — where fame turns into murder
By Michael Earl Simmons
This is Part 1 of a two-part story…
Pensacola didn’t meet Roland Lalone first.
Connecticut did.
Massachusetts did.
And by the time the Gulf Coast finally caught his scent, the man had already left a trail of cold rooms, hot gun barrels, and one dead trooper lying in a stranger’s driveway. But I’m getting ahead of myself.
I found this story the way you find the best trouble—quietly, in a back corner, where nobody’s looked in a long time. Since retiring from the Pensacola Police Department, they still let me nose around the old files. The log books. The hand-written arrest slips. The murder folders that smell like paper, sweat, and decisions that can’t be taken back.
One afternoon, I slid open what I call the murder file cabinet—the one that holds the old, old, old stuff—and a stack of papers stared back at me like they’d been waiting. It wasn’t a report.
It was a script. A real radio drama script, formatted like something you’d hear crackling out of a big wooden console in 1930—men in hats talking fast, women clutching pearls, footsteps in alleys, sirens that sound like wolves.
I recognized names. Chief Willie O’Connell. Archie Bowman. Andrew Schmitz.
But I didn’t recognize the case. So I dug until the story came up in my hands. And when it did, I understood why a radio company wanted it. Because it moves like a film: a stolen car, a string of robberies, a running gunfight, a trooper murdered on a dark Connecticut road… and then—like all bad men eventually do—the fugitives drift south, toward salt air and shadows.
Worcester: Where the Devil Learns to Drive
They say “Wuhster.” Worcester, Massachusetts—old stone, old mills, old streets that remember boots and hard winters. It’s the kind of place where trouble doesn’t need to be invited. It grows there. That’s where Roland Lalone learned the shape of a cell door.
He met an older man, Clarence Harrington, in jail. Clarence had years on him, but Roland had the wheel. Even then you can feel it—some men lead with their eyes. Some with their voice. Roland led with certainty, the kind that makes weaker people follow without asking why.
When they got out, Roland’s plan was quick money: jewelry stores at night. In and out. Small towns, big take.
They stole a car first—a new Buick Brougham off Olean Street—and headed for Adams, Massachusetts, a picture-postcard town dressed in December like it was meant for a holiday magazine: cedar, poplar, red maple, church steeples and farmhouses, cold sky over a ribbon of road.
But Roland couldn’t wait for the “big plan.” He needed a warm-up. So he walked into Schwartz and Son with a forged check in his pocket and a coat on his mind. Clarence cashed it, shaky as a leaf, and walked out with an overcoat and $25.30. For a moment it felt like they’d beaten the world.
Then the cashier’s suspicion turned into a phone call, and the phone call turned into a bulletin, and the bulletin turned into flashing eyes looking for a stolen car and two men wearing the kind of nervousness that doesn’t wash off.
Their Buick broke down near Pittsfield, and when officers started asking questions, Roland did what he’d do again and again: He ran. He left Clarence to take the full weight of it.
Roland didn’t stay loose long. State policemen found him wandering a deserted mountain road at 2:30 a.m. with a story that didn’t fit the hour. They put him back where he belonged: behind bars, beside Clarence, in front of a veteran interrogator who knew the town and knew the people and—most importantly—knew the man Roland tried to cheat.
They confessed. They got a year. Roland came out free—not rehabilitated, educated.
Springfield: The City of Firsts, and Their First Big Legend
By 1928, Roland had upgraded partners. Now it was Albert Raymond—another ex-con with a hunger for fast money and a willingness to do what was needed. Springfield became their stage. They walked into stores like they belonged there. Then out came the pistols, the orders, the fear.
They’d strip wallets, empty registers, pry open safes. Then they’d shove people into whatever “back room” existed. Sometimes that back room was an ice box. That’s how Springfield started saying the name like a curse: The Ice Box Bandits.
Ten robberies, same method, same swagger. And the newspapers did what newspapers do: they built monsters. Roland liked it. You can feel that in the story—the way he enjoyed the attention, the way he began to believe the laws of consequence didn’t apply to him. Then he made the mistake that ends most sprees: He got careless.
They stole a luxury Black Willys-Knight touring car and kept it longer than they should’ve. The owner noticed fast. A bulletin went out. A patrol officer in Springfield spotted that exact car sitting outside a store during a robbery.
On Friday, April 6, 1928, a Springfield motorcycle officer named Raymond Gallagher saw the Willys-Knight pull off and followed. The fugitives didn’t stop. The passenger opened fire. The gunshots weren’t dramatic now—they were real, ripping air and metal. A running gun battle rolled through neighborhoods.
One bullet punched through Gallagher’s sleeve. Gallagher’s return fire shattered the rear window of the Willys-Knight. Then the touring car bumped the motorcycle. Gallagher crashed. He lived.
But the Ice Box Bandits had crossed a line. They weren’t just thieves with a gimmick anymore. They were armed men willing to shoot a cop and gamble on the road.
Pomfret: When It Turned Into Murder
They ran for the Connecticut state line like it was a magic wall. It wasn’t. Alerts went out across Massachusetts, Rhode Island, and Connecticut: stolen car, armed suspects, last seen leaving a robbery at 5:45 p.m.
A Connecticut State Policeman named Irving Nelson heard it. A former WWI soldier, a motorcycle man, the type who believed the badge meant you go toward the trouble. He spotted the speeding car on State Highway 97 and closed in. He started to pull alongside.
Gunfire erupted from the car. Nelson pulled into a driveway, got off his motorcycle, and collapsed. He died there—two days before Easter—while his wife and small son waited at home with plans that would never happen.
That’s the moment the story freezes. Up to then, it was robbery. After that, it was cop-killing murder. And now every officer in three states had the same thought: Find them.
They ditched the car in Webster, Massachusetts. And the case tightened because of something that still feels like old-fashioned police work at its finest: a fifteen-year-old gas station kid in Willimantic named Harold Lester, who noticed the shattered window, the bullet holes, the silent men… and memorized the tag number like it mattered.
It did.
It always does.
End of Part 1