The horse-drawn caisson carrying the remains of 38-year-old George "Alexi" Whitney at Arlington National Cemetery in July. Picture: Ian Shapira/Washington Post
They came from all corners of his life. His New England boarding school. His small liberal arts college. The Marines. And the CIA.

Family, friends, and colleagues gathered on a summer Monday to pay tribute to George "Alexi" Whitney, who was killed in Afghanistan just before Christmas in 2016 and was finally being buried at Arlington National Cemetery.

His family had fought hard for that honour. Because the 38-year-old was a CIA contractor when he died, they needed special permission for his remains to be buried underground, rather than in the columbarium. They'd enlisted the aid of Mike Pompeo, the former director of the CIA, which had recognized Whitney with a star on its Memorial Wall without publicly acknowledging its affiliation with him.

The July 23 ceremony at Arlington appeared to be like one of the many funerals held here for a slain U.S. service member. Six horses pulled a caisson carrying a flag-draped coffin containing his urn. A bugler played taps.

But Whitney is among a tiny group of CIA contractors killed in the longest war in U.S. history. That includes Jeremy Wise and Dane Paresi, who were among the seven agency operatives killed in 2009 by a suicide bomber in Khost, one of the deadliest attacks in CIA history; and Jay Henigan, an agency contractor and plumber killed in Kabul in 2011.

Overall, the war has claimed the lives of more than 1,700 U.S. contractors, according to one Labor Department report, and nearly 2,400 American service members, according to the Defense Department.

George "Alexi" Whitney at his father's home in South Florida in 2016. Photo courtesy of the Whitney family.
"All wars are futile," said Alexi's father, George Whitney III, speaking about his son's death publicly for the first time. But going to Afghanistan is "what Alexi wanted. He thought he was doing the right thing, and that's all that counts for me."

But Whitney's ex-wife, a former CIA officer, knew something else: Despite the CIA star and Pompeo's help arranging an Arlington burial, Whitney's career at Langley was turbulent, and he often felt like the agency he loved dismissed his talents.

Whitney wasn't even supposed to be in Afghanistan. He had been planning to spend the 2016 holiday season at his father's home in South Florida. Then a mission suddenly came up, and Whitney volunteered.

The trip was risky: Two of Whitney's friends in the CIA's paramilitary force, Brian Hoke and Nate Delemarre, had been killed in Afghanistan two months earlier.

"My understanding was that Alexi went back because they were on to the people who killed Brian and Nate. It was his intention to track those people down," said Whitney's 72-year-old father, George Whitney III, who was briefed on his death by an agency official.

So, a week before Christmas, Whitney and several other teammates lined up outside a building in the Jalalabad area, poised to assault a compound of insurgents, his father said. A helicopter was surveilling above, but no one saw an insurgent slip out a back exit of the structure.

The assailant sneaked around and shot Whitney in the shoulder, his father said, and the impact spun him around, allowing the gunman to fire at his face. He was airlifted to a hospital, but the injuries were too extensive.

"I know my son extremely well, and he was very passionate about this job and passionate about this team," his father said. "Whatever building the agency was attacking - it's now gone. My hope is they killed everybody."

In some ways, Whitney was an unlikely warrior.

He was born into a patrician family. His great-great-grandfather was Robert Bacon, secretary of state under President Theodore Roosevelt. His great-uncle, Richard Whitney, the onetime president of the New York Stock Exchange, helped prop up the market during the great crash of 1929.

Growing up in Vermont and Massachusetts, Whitney was surrounded by his father's military books. His grandfather George Whitney Jr. served on a Navy destroyer in the Pacific during World War II.

"Alexi's Christmas list one year was for a set of books on the rise and fall of the Roman Empire," said his sister Larissa Whitney, 38, a landscape architecture graduate student in Northern Virginia. "Who asks for that when they're 14? I wanted a dolphin and a puppy."

Whitney wrestled and played football and lacrosse at Brooks School, a coed boarding academy north of Boston. By the time he got to Bates College in Maine, he was talking about joining the Marines. He told his mother, Caryn Whitney, that he didn't want a deskbound life.

Still, his decision to enlist after graduating from Bates in 2000 stunned his friends.

"You don't see boarding-school, Bates WASPy kids joining the military," said Liz Forbes, a close friend. "We were like, 'Wait a second, you're George Whitney.' "

The remains of George "Alexi" Whitney at Arlington National Cemetery, where the family received a waiver to bury him. Picture: Ian Shapira/Washington Post
He arrived on the front lines in Iraq in early 2005, at a time when the war was killing more than 800 U.S. service members a year. Based in Anbar Province, Whitney, then a first lieutenant, led a platoon within the selective Third Reconnaissance Battalion, searching for insurgents and clearing roadside bombs.

"There are people out there that want to kill you every day," he told a crew for the documentary "Marine Recon," which aired on the Military Channel. "They are cautious and very smart."

Late in his deployment in 2005, Whitney's platoon got a tip on the location of a high-value insurgent. He was under new orders not to detain such individuals until his superiors gave him the green light. But Whitney, now a captain whom comrades called "Lex," arrested the suspect anyway. He feared the man would escape, according to his father.

It was a disastrous move. Whitney underwent a disciplinary hearing known as a board of inquiry, and was honorably discharged in 2006.

"He was horrified," his father said. "He was so depressed."

Out of the Marines, Whitney set his sights on the intelligence community.

In the spring of 2008, the CIA hired him as a case officer. Two years later, Whitney, who had married a boarding-school classmate, was on his way to the agency's station in Karachi, Pakistan.

"He wanted to take down terrorists," said Iona Segaram (pronounced Say-gram), who worked alongside him there. "When he got to Karachi, he was beyond thrilled."

Although she regarded herself as a weary midcareer officer and Whitney as the idealist, the two instantly bonded. Segaram, who had served abroad elsewhere, mentored Whitney in tradecraft.

But then, for the second time in his career, Whitney had a conflict with a superior. Shortly after the May 2, 2011, raid on Osama bin Laden's compound in northern Pakistan, one of his bosses filed a complaint accusing him of insubordinate behaviour, said Segaram, who wouldn't divulge the details.

"It became this blowup," Segaram said. "A lot of people came forward to vouch for him, but not enough to exonerate him, and he had to go through a counselling process. They put something in his file. The agency was trying to be fair, but it broke his heart, totally. He felt abandoned. He felt humiliated. It probably started him on a journey of redemption that ended in his death."

The CIA declined to comment.

Shortly before he left Pakistan in 2011, he confessed something to Segaram: He loved her.

Shocked, Segaram told him he had to resolve things with his wife, Lisa Bottomley, who was living in Boston and working part-time for a nonprofit group that aids children in Tanzania.

"The morning after he flew back to the States, he broke up with me," Bottomley said. "I wasn't expecting sunshine and rainbows when he got home, but I had no idea this was coming."

After the divorce, he and Segaram left the CIA and got married. They moved to Texas, where Segaram worked for an oil company and he took a job at a consulting firm doing investigative work.

But Whitney yearned for a greater mission and itched to get back to the CIA, she said. His attempts went nowhere. The agency was loath to offer him another chance after his problems in Pakistan and his subsequent rejection of a posting in Africa.

George "Alexi" Whitney served in the Marines for six years and deployed to Iraq in 2005, where he led a platoon looking for insurgents and clearing roadside bombs. He was killed in Afghanistan in 2016. Photo courtesy of George Whitney
Eventually, Whitney got what he considered the next-best thing: a CIA contracting job.

"It was dangerous. But he was with his Marine mafia friends again and felt comfortable," said Segaram, who declined to offer more details about the job.

Even so, the inconsistent rhythms of an agency contractor - with frequent back-and-forth trips abroad - felt less satisfying than the career of a CIA case officer playing a central role in Langley's mission, she said.

By the time he left for Afghanistan in 2016, their marriage had ended but they remained close. She knew he faced the same risks as Hoke and Delemarre, his slain friends in the CIA's paramilitary unit.

"He was devastated by their deaths. He started to realize this kind of work has consequences," Segaram said. "I said, 'Are you sure you want to go?' I begged him not to."

On Dec. 17, Segaram texted him in the morning: "Hope you are staying safe and warm."

She never heard back.

His father was the first in the family to get the news. Distraught, he called his daughter Larissa, who accused him of lying.

"My reaction was to be mad at the bearer of bad news," Larissa recalled. "It was like an alternate reality."

A memorial service was held in January at the Brooks School. By May 2017, three black stars had been engraved on the iconic white marble Memorial Wall in the agency's lobby denoting the deaths of Whitney, Hoke and Delemarre. But their names were not calligraphed into the agency's Book of Honor - which sits open on a shelf encased in glass below the wall - because their affiliation with the agency is still considered secret. A few months later, the secret got out when the New York Times revealed their links to Langley.

The CIA honoured George Whitney by engraving a star on its Memorial Wall but also presented his family with a star replica, which sits on his father's desk in South Florida. Photo courtesy of George Whitney.

The Whitneys wanted Alexiburied at Arlington, as he'd requested in his will. As they waited for the cemetery to grant permission, they contacted Pompeo, then the CIA director.

"Mr. Whitney, If you request a waiver, you have my full support," Pompeo wrote to Whitney's father.

Months later, the family got its wish - and the coordinates to their son's gravesite.

After a U.S. flag was folded and given to Whitney's mother, the mourners hugged and tucked away their programs, featuring a photo of Alexias a child clutching a toy gun with a hat concealing his face. A handful of thickly bearded men walked to the nearby gravesites of Hoke and Delemarre, where they lightly tapped the backs of their headstones.

Then, the Whitneys walked alone to gravesite 11847 in Section 60. They knelt down and took one last look at the cremation box, its top engraved with his monogram: GWA.

The Washington Post