Army specialist Terry Holdbrooks had been a guard at Guantánamo for about six months the night he had his life-altering conversation with detainee 590, a Moroccan also known as "the General." This was early 2004, about halfway through Holdbrooks's stint at Guantánamo with the 463rd Military Police Company. Until then, he'd spent most of his day shifts just doing his duty. He'd escort prisoners to interrogations or walk up and down the cellblock making sure they weren't passing notes. But the midnight shifts were slow. "The only thing you really had to do was mop the center floor," he says. So Holdbrooks began spending part of the night sitting cross-legged on the ground, talking to detainees through the metal mesh of their cell doors.

He developed a strong relationship with the General, whose real name is Ahmed Errachidi. Their late-night conversations led Holdbrooks to be more skeptical about the prison, he says, and made him think harder about his own life. Soon, Holdbrooks was ordering books on Arabic and Islam. During an evening talk with Errachidi in early 2004, the conversation turned to the shahada, the one-line statement of faith that marks the single requirement for converting to Islam ("There is no God but God and Muhammad is his prophet"). Holdbrooks pushed a pen and an index card through the mesh, and asked Errachidi to write out the shahada in English and transliterated Arabic. He then uttered the words aloud and, there on the floor of Guantánamo's Camp Delta, became a Muslim.

When historians look back on Guantánamo, the harsh treatment of detainees and the trampling of due process will likely dominate the narrative. Holdbrooks, who left the military in 2005, saw his share. In interviews over recent weeks, he and another former guard told NEWSWEEK about degrading and sometimes sadistic acts against prisoners committed by soldiers, medics and interrogators who wanted revenge for the 9/11 attacks on America. But as the fog of secrecy slowly lifts from Guantánamo, other scenes are starting to emerge as well, including surprising interactions between guards and detainees on subjects like politics, religion and even music. The exchanges reveal curiosity on both sides—sometimes even empathy. "The detainees used to have conversations with the guards who showed some common respect toward them," says Errachidi, who spent five years in Guantánamo and was released in 2007. "We talked about everything, normal things, and things [we had] in common," he wrote to NEWSWEEK in an e-mail from his home in Morocco.

Holdbrooks's level of identification with the other side was exceptional. No other guard has volunteered that he embraced Islam at the prison (though Errachidi says others expressed interest). His experience runs counter to academic studies, which show that guards and inmates at ordinary prisons tend to develop mutual hostility. But then, Holdbrooks is a contrarian by nature. He can also be conspiratorial. When his company visited the site of the 9/11 attacks in New York, Holdbrooks remembers thinking there had to be a broader explanation, and that the Bush administration must have colluded somehow in the plot.

But his misgivings about Guantánamo—including doubts that the detainees were the "worst of the worst"—were shared by other guards as early as 2002. A few such guards are coming forward for the first time. Specialist Brandon Neely, who was at Guantánamo when the first detainees arrived that year, says his enthusiasm for the mission soured quickly. "There were a couple of us guards who asked ourselves why these guys are being treated so badly and if they're actually terrorists at all," he told NEWSWEEK. Neely remembers having long conversations with detainee Ruhal Ahmed, who loved Eminem and James Bond and would often rap or sing to the other prisoners. Another former guard, Christopher Arendt, went on a speaking tour with former detainees in Europe earlier this year to talk critically about the prison.

Holdbrooks says growing up hard in Phoenix—his parents were junkies and he himself was a heavy drinker before joining the military in 2002—helps explain what he calls his "anti-everything views." He has holes the size of quarters in both earlobes, stretched-out piercings that he plugs with wooden discs. At his Phoenix apartment, bedecked with horror-film memorabilia, he rolls up both sleeves to reveal wrist-to-shoulder tattoos. He describes the ink work as a narrative of his mistakes and addictions. They include religious symbols and Nazi SS bolts, track marks and, in large letters, the words BY DEMONS BE DRIVEN. He says the line, from a heavy-metal song, reminds him to be a better person.

Holdbrooks—TJ to his friends—says he joined the military to avoid winding up like his parents. He was an impulsive young man searching for stability. On his first home leave, he got engaged to a woman he'd known for just eight days and married her three months later. With little prior exposure to religion, Holdbrooks was struck at Gitmo by the devotion detainees showed to their faith. "A lot of Americans have abandoned God, but even in this place, [the detainees] were determined to pray," he says.

Holdbrooks was also taken by the prisoners' resourcefulness. He says detainees would pluck individual threads from their jumpsuits or prayer mats and spin them into long stretches of twine, which they would use to pass notes from cell to cell. He noticed that one detainee with a bad skin rash would smear peanut butter on his windowsill until the oil separated from the paste, then would use the oil on his rash.

Errachidi's detention seemed particularly suspect to Holdbrooks. The Moroccan detainee had worked as a chef in Britain for almost 18 years and spoke fluent English. He told Holdbrooks he had traveled to Pakistan on a business venture in late September 2001 to help pay for his son's surgery. When he crossed into Afghanistan, he said, he was picked up by the Northern Alliance and sold to American troops for $5,000. At Guantánamo, Errachidi was accused of attending a Qaeda training camp. But a 2007 investigation by the London Times newspaper appears to have corroborated his story; it eventually helped lead to his release.

In prison, Errachidi was an agitator. "Because I spoke English, I was always in the face of the soldiers," he wrote NEWSWEEK in an e-mail. Errachidi said an American colonel at Guantánamo gave him his nickname, and warned him that generals "get hurt" if they don't cooperate. He said his defiance cost him 23 days of abuse, including sleep deprivation, exposure to very cold temperatures and being shackled in stress positions. "I always believed the soldiers were doing illegal stuff and I was not ready to keep quiet." (Navy Cmdr. Jeffrey Gordon, a Pentagon spokesman, said in response: "Detainees have often made claims of abuse that are simply not supported by the facts.") The Moroccan spent four of his five years at Gitmo in the punishment block, where detainees were denied "comfort items" like paper and prayer beads along with access to the recreation yard and the library.

Errachidi says he does not remember details of the night Holdbrooks converted. Over the years, he says, he discussed a range of religious topics with guards: "I spoke to them about subjects like Father Christmas and Ishac and Ibrahim [Isaac and Abraham] and the sacrifice. About Jesus." Holdbrooks recalls that when he announced he wanted to embrace Islam, Errachidi warned him that converting would be a serious undertaking and, at Guantánamo, a messy affair. "He wanted to make sure I knew what I was getting myself into." Holdbrooks later told his two roommates about the conversion, and no one else.

But other guards noticed changes in him. They heard detainees calling him Mustapha, and saw that Holdbrooks was studying Arabic openly. (At his Phoenix apartment, he displays the books he had amassed. They include a leather-bound, six-volume set of Muslim sacred texts and "The Complete Idiot's Guide to Understanding Islam.") One night his squad leader took him to a yard behind his living quarters, where five guards were waiting to stage a kind of intervention. "They started yelling at me," he recalls, "asking if I was a traitor, if I was switching sides." At one point a squad leader pulled back his fist and the two men traded blows, Holdbrooks says.

Holdbrooks spent the rest of his time at Guantánamo mainly keeping to himself, and nobody bothered him further. Another Muslim who served there around the same time had a different experience. Capt. James Yee, a Gitmo chaplain for much of 2003, was arrested in September of that year on suspicion of aiding the enemy and other crimes—charges that were eventually dropped. Yee had become a Muslim years earlier. He says the Muslims on staff at Gitmo—mainly translators—often felt beleaguered. "There was an overall atmosphere by the command to vilify Islam." (Commander Gordon's response: "We strongly disagree with the assertions made by Chaplain Yee").

At Holdbrooks's next station, in Fort Leonard Wood, Mo., he says things began to unravel. The only place to kill time within miles of the base was a Wal-Mart and two strip clubs—Big Daddy's and Big Louie's. "I've never been a fan of strip clubs, so I hung out at Wal-Mart," he says. Within months, Holdbrooks was released from the military—two years before the end of his commitment. The Army gave him an honorable discharge with no explanation, but the events at Gitmo seemed to loom over the decision. The Army said it would not comment on the matter.

Back in Phoenix, Holdbrooks returned to drinking, in part to suppress what he describes as the anger that consumed him. (Neely, the other ex-guard who spoke to NEWSWEEK, said Guantánamo had made him so depressed he spent up to $60 a day on alcohol during a monthlong leave from the detention center in 2002.) Holdbrooks divorced his wife and spiraled further. Eventually his addictions landed him in the hospital. He suffered a series of seizures, as well as a fall that resulted in a bad skull fracture and the insertion of a titanium plate in his head.

Recently, Holdbrooks has been back in touch with Errachidi, who has suffered his own ordeal since leaving the detention center. Errachidi told NEWSWEEK he had trouble adjusting to his freedom, "trying to learn how to walk without shackles and trying to sleep at night with the lights off." He signed each of the dozen e-mails he sent to NEWSWEEK with the impersonal ID that his captors had given him: Ahmed 590.

Holdbrooks, now 25, says he quit drinking three months ago and began attending regular prayers at the Tempe Islamic Center, a mosque near the University of Phoenix, where he works as an enrollment counselor. The long scar on his head is now mostly hidden under the lace of his Muslim kufi cap. When the imam at Tempe introduced Holdbrooks to the congregation and explained he'd converted at Guantánamo, a few dozen worshipers rushed over to shake his hand. "I would have thought they had the most savage soldiers serving there," says the imam, Amr Elsamny, an Egyptian. "I never thought it would be someone like TJ."

With Dina Fine Maron in Washington

© 2009