Angus R. McCoubrey and his friend knew their way around Brookline and were certain of two things: their taxi driver was taking a roundabout route to run up the meter, and they weren’t paying the full fare.

So as they got out of the cab that day in April 2013, one of them tossed a $5 bill onto the front seat, $2 less than the fare, and walked away. Convinced he had been cheated, the driver flagged down a Brookline police officer, who wrote up the dispute.

Three months later, the officer sought a criminal charge against McCoubrey: taxi fare evasion.

But by then, the 28-year-old had left Brookline for New York without leaving a forwarding address.

Nine years later, that $2 dispute came crashing back into his life in truly bizarre fashion, leaving a bewildered McCoubrey, in swim trunks, T-shirt, and flip flops, handcuffed in a Chilmark police cruiser after being involved in a fender-bender in a beach parking lot.

He was under arrest for ignoring a felony charge in Brookline District Court.

Somehow, someone in a Brookline court filling out charging documents had dropped the “i” in taxi, along with the word “fare,” transforming a misdemeanor into a felony.

“I’m a fan of Franz Kafka,’’ McCoubrey said ishortly after his arrest on Aug. 21. “But I never thought I was going to be a character in a Kafka novel.”

Like Kafka’s protagonist in “The Trial,” McCoubrey, now a 37-year-old Philadelphia advertising executive, found himself swallowed up by the criminal justice system for the next two days, as he and his wife, Laura, desperately waited for a chance to convince police, a bail commissioner, and a Martha’s Vineyard judge that it was all a big mistake.

He had only lived in Brookline for six weeks and that was in a rented room, was never in a position to owe taxes, and the taxi fare dispute was his only interaction with the criminal justice system, McCoubrey wanted to say. But he’d have to wait and tell it to the judge in Brookline. And, getting there wouldn’t be easy.

“Funny, sometimes people don’t tell police the truth,” Chilmark Police Chief Jonathan Klaren said drolly. “But we don’t know the particulars of a case. . . . And if there’s a court saying,, ‘You’re hereby commanded to bring this person in,’ you know, there’s really not much we can do.”

After his arrest, McCoubrey was handed over to the Dukes County Sheriff’s Department, Klaren said. McCoubrey said the Chilmark officers were very professional and told him he would probably be out on bail in a few hours.

It didn’t turn out that way. Melissa Lawry was the bail commissioner that Sunday night. And her hands were tied.

“I said it was non-bailable and they would have to hold onto him. And that’s pretty much it, that’s pretty much the gist of the story,’’ said Lawry, who would later learn about the mix-up, which was first reported by The Vineyard Gazette.

“It was listed as tax evasion, which obviously was an error,” Lawry said. “I don’t do research of any type. I get the call from the jail. They tell me what the warrant says. It’s the default warrant protocol. And bail was not available.”

McCoubrey, who has summered on the Vineyard since he was a boy, said a deputy delivered the bad news, and also told him that Edgartown District Court would be open the next morning and maybe he could tell his tale to the judge over Zoom.

Shortly before noon, his case was called before Judge Paul G. Pino and in short order the judge made his decision, according to the official recording of the session. McCoubrey never appeared on Zoom.

“All right,” Pino said after the sound of shuffled papers is heard. “We will have him transported” to Brookline.

But as visitors to the island well know, securing a car reservation on the Steamship Authority ferry can be tough, especially on an afternoon in August. McCoubrey said he was told around noon that he’d be staying in jail another day.

Dukes County Sheriff Robert W. Ogden did not respond to requests for comment. Sean Driscoll, a spokesman for the Steamship Authority, said, “We were pretty full on that day, but our customer policies allow us to bump other reservations if needed for emergency transport.”

“If necessary we would make room for such a transport on an appropriate trip,” Driscoll said by e-mail.

Tuesday morning arrived and so did the deputies tasked with getting McCoubrey to Brookline. His hands and feet shackled to his waist “like a murderer,” he was put into a prisoner transport van for the 7:30 a.m. ferry, he said. He was then driven from Hyannis to the Brookline courthouse.

“When you’re in that system, you literally get the wrong information so many times. I stopped believing anything,’’ McCoubrey said. “I was pretty despairing. . . . I was honestly worried that I was going to go to jail in Brookline for tax evasion.”

Once in Brookline, McCoubrey met a tax lawyer his family had hired. The lawyer told him the court realized there had been a mistake and the charges would be dismissed.

His nearly two-day ordeal was nearing an end. But exactly how it happened at all remains a mystery.

In response to Globe questions, Clerk Magistrate Edward Savage said McCoubrey was told by police in 2013 there would be court proceedings and to expect a notice by mail. The court twice mailed information about court dates to the Brookline address McCoubrey gave police, Savage said.

“Mr. McCoubrey did not contact the court to provide an updated mailing address,” he said.

Savage acknowledged that the key error — turning a taxi fare evasion case into the far more serious tax evasion charge — was committed by the court. “The court regrets that in preparing the criminal complaint and summons a clerical typographical error occurred and the charge listed on the criminal complaint was for the crime of tax evasion,’’ Savage wrote.

When McCoubrey failed to appear in court in September 2013, an arrest warrant was issued for tax evasion.

Norfolk District Attorney Michael Morrissey’s office said it uncovered another mistake: Brookline police cited the wrong statute when seeking the taxi fare evasion charge, invoking a state law that applies only to MBTA fare evasion. The Brookline officer could not be reached for comment.

In the end, McCoubrey never got his chance to speak to a judge. Before McCoubrey was taken to the Brookline courthouse, a prosecutor told Judge Debra Shopteese about the mistakes and said they would drop the case. The judge formally terminated it around 10:40 a.m. Tuesday.

McCoubrey walked out of the courthouse still wearing his beachwear. Sunday seemed like a long time ago.

“I did learn, you know, when you’re in a holding cell, you really rely on the support and kindness of your family and friends, because you’re really powerless,’’ he said. “I know not everyone’s so lucky.”

McCoubrey said he now regrets not paying the $2 to the cab driver, a decision he attributes to his relative youth. But how that spiraled into two days in jail still eludes him.

“It just doesn’t compute in my brain,” he said. “It still doesn’t make any sense.”

McCoubrey was given back his wallet and cellphone and bought himself a coffee. He then thought about getting down to Woods Hole to take a ferry back to Chilmark.

John R. Ellement can be reached at john.ellement@globe.com. Follow him on Twitter @JREbosglobe.

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