Philippe Holland has bullet fragments in his brain and a permanent seizure disorder. The slug that a Philadelphia police officer fired into his jaw on an April night in 2014 was removed only last year.

It was those injuries - "Horrible. Devastating," Holland's lawyer called them - that led, on Friday, to the biggest settlement in a police shooting that the city of Philadelphia has ever paid.

The former deliveryman, mistakenly shot while ferrying a cheeseburger to a Southwest Philadelphia house, will collect $4.4 million in the settlement, nearly twice the amount of the next largest police-shooting payout.

"The City settled this case considering a number of factors, including the severity of Mr. Holland's injuries sustained during this unfortunate and regrettable series of events," mayoral spokesman Michael Dunn wrote in an email, "and the City's potential exposure at trial."

From the start, city officials spoke differently about Holland's case. A day after the shooting, then-Commissioner Charles H. Ramsey said flat-out that Holland had been shot mistakenly, and met with his mother in the hospital. Ramsey called Holland a good young man who came from a good family. He said the officers who shot him "felt terrible."

It was clear the commissioner thought something had gone terribly wrong.

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Holland was 20 and taking college courses at Delaware County Community College in April 2014, working two jobs on the side: a gig at the airport Au Bon Pain, and a pizza delivery job he'd only had for three weeks, at a neighborhood shop in West Philadelphia called Slices & More.

He and his mother had moved to Philadelphia from Cote d'Ivoire when he was a toddler. A 2011 graduate of Upper Darby High School, he was majoring in communications. He hoped to become a sportscaster.

Holland had one mark on his record - the week before he was shot, he was arrested on a domestic violence change - during an argument he threw a cellphone at his girlfriend, striking her. A judge required him to attend anger-management classes.

The following accounts are drawn from court documents obtained by The Inquirer from Holland's lawyer, Thomas Kline:

On the night of April 22, 2014, Holland's new job sent him to the 5100 block of Willows Street with a Double Cheeseburger Deluxe.

Officers Kevin Hanvey and Mitchell Farrell were there, too, in plainclothes, investigating a report of gunshots in the area. They had been on the job less than a year - to make it to a plainclothes detail that early was something of a distinction, Farrell would later say in a sworn deposition.

Holland parked his Ford Taurus, walked up to the house on Willows Street with the cheeseburger, and handed it to the woman at the door.

Twenty seconds later, she would tell police, she heard a barrage of shots ring out from the street.

Holland told investigators that he saw Farrell and Hanvey's unmarked car swerve, and he thought he was about to get robbed.

"In case it was something bad," he said in a deposition, "I didn't want whoever was in that car to see me."

So he slipped into the car through the passenger-side door.

Hanvey and Farrell told investigators they approached Holland because they saw him walking past a Chinese restaurant on 51st Street, and asked a witness on the street where the gun shots she'd heard had come from. They said the woman had pointed toward Holland and said the shots came from where he was walking.

But the woman later told police she had only pointed toward the Chinese store, and hadn't seen Holland at all. And the store's surveillance camera didn't capture Holland nearby, a police investigation found.

The officers said they yelled "Stop! Police!" several times at the pizza deliveryman.

But Holland said they never identified themselves, and the witness near the Chinese store said she never heard the officers shout "Police!" either.

As Holland slid into the driver's seat, he said, all he could see was a man shining a light into his face - and another man holding a gun.

"You just - you see the gun, and you go into survival mode," he said later in a deposition.

Holland said he tried to pull out of the parking space. And that's when the officers opened fire, he said. He remembers the pain of a bullet coursing into his right thigh, the crunch of the car windows breaking, and the smack of the Taurus into a fence across the street.

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Hanvey and Farrell said they had feared for their lives when Holland peeled out of his parking spot. Farrell said in a deposition there was no time to get out of the way of the car.

"My training is what kicked in," he told Holland's lawyers, "which saved my life."

At the time, it was against police regulations for officers to fire at a moving vehicle unless someone inside the car was threatening them or someone else with some form of deadly force - other than the vehicle itself.

An Internal Affairs review of the case noted that "Holland drove his vehicle toward both officers, endangering their lives." But investigators also wrote that, just before the shooting, Hanvey had placed himself in front of Holland's car, and that Farrell had stationed himself "in the middle of the street with no cover or concealment available to him."

"An officer should never unnecessarily place themselves or another person in jeopardy in an attempt to stop a vehicle," the Internal Affairs memo noted. "There was no other threat posed by Holland other than the moving vehicle."

The District Attorney's office declined to press charges in the case. The department's Use of Force Review Board concluded that Farrell and Hanvey had violated department policy.

A police spokesman said the two have been on administrative duty since the shooting, and that "discipline is still pending."

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Holland's settlement dwarfs city payouts following prior police shootings. The next-largest payout - $2.5 million - went to Stephen Moore, an unarmed water-ice vendor shot in the chest in his home in 2011 by a police officer investigating a report of a burglary.

Another $2.5 million went to the family of Jamil Moore, who was a passenger in a stolen car involved in a 2011 police chase that ended with officers firing 62 times into the car. Moore was also unarmed.

Holland's settlement also comes with promised policing reforms: The police department has agreed to establish a new protocol for plainclothes officers' dress and behavior so it is clear they are police.

"The City of Philadelphia strives to earn, maintain, and build . . . trust by ensuring that police act within the scope of their lawful authority and hold paramount the civil rights of those they serve," Commissioner Richard Ross said in a statement Friday.

Kline says his client hopes the new policy will be known as the Holland Police Training Protocol.

"[Holland] is very gratified to see that there was a recognition not only financially, but in the need to train police officers," Kline said.

Holland declined through Kline to speak to a reporter about his case. In the years since the shooting, he said in a deposition last year, he has worked to get his life back on track, with a job that lets him work some days from home. Seizures have prevented him from driving.

After the shooting, he carried his mother's knife for protection - "a little blade" - even on trips to the corner store. He is taking community college courses again - still majoring in communications. But he's abandoned the old dream of being a sports broadcaster.

"You know, a near-death experience is going to change how you see things," he said in the deposition. "And the way I looked at it - not that sports isn't important, but, I mean, in the grand scheme of things, I wanted to do something that mattered."

He said he wasn't sure yet what that might be.

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@aubreyjwhelan