Questions haunt prisons chief slaying case Evan Ebel fantasized in a letter about killing prison guards He is believed to be the man who shot Colorado's prisons chief to death "From the beginning" he had "a streak of cruelty," says the governor, a friend of his father Did a crackdown on a prison white supremacist gang figure into the shooting? (CNN) -- The man believed to be the one who killed Colorado's prisons chief fantasized in a letter to a friend about torturing and killing guards at the state correctional facility where he was incarcerated. He signed it "Evil Evan Ebel." Whether it was meant as a joke or something more sinister may never be known. Ebel took the answer with him. He died after a shootout with authorities in northern Texas just days after, investigators say, he killed state Department of Corrections chief Tom Clements and Nathan Leon, a 22-year-old pizza deliveryman. The letter has since become one more piece of a confusing and sometimes confounding case that unfolded after a clerical error led to Ebel's release from prison four years early. Then, according to parole officials, it took Colorado authorities five days to discover that the parolee with ties to a white supremacist prison gang had disabled his ankle monitor and was on the loose. The revelations have a raised a larger question: Could it all have been prevented? The answer is as confusing as the case. Gunshot at the door It began with the doorbell. It was just after 8:30 p.m. on March 19 as a black Cadillac sat idling, empty, 200 yards from Clements' home in Monument, just north of Colorado Springs. The prisons chief with a reputation for prison reforms and a crackdown on prison gangs -- including the 211 Crew, the white supremacist gang Ebel belonged to -- was home watching television with his wife, Lisa. They weren't expecting anyone at that hour. But they had lived in the upscale community with its winding roads long enough to know that people unfamiliar with the area sometimes got lost, and sometimes rang the wrong doorbell. Clements opened the door to find a gunman, who authorities believe may have been disguised as a pizza deliveryman. The gunman said nothing. He just pulled the trigger, hitting the prisons chief in the chest, Clements' wife later told investigators. She called 911, pleading for help to save her husband as he lay bleeding to death on the stairs of their home. In the days that followed, investigators worked to develop leads, appealing to the public for help in the search for the killer. Hundreds of miles away, in northern Texas, another part of the story was playing out, one that would link Ebel to the killings of Clements and Leon. A streak of cruelty By all accounts, Ebel came from a privileged upbringing. His father, Jack Ebel, an attorney and former oil executive, counts Colorado Gov. John Hickenlooper among his friends. "From the beginning, his son just seemed to have this bad streak, a streak of cruelty, and anger," Hickenlooper said on CNN's "State of the Union." They worked with Evan again and again, but to no avail. By the time most teens are in their first year of college or work after high school, Ebel was looking at hard time for armed robbery, menacing and a variety of other charges after putting a gun to the head of an acquaintance and demanding money. Prison records show that almost from the moment Ebel began serving his eight-year sentence in 2005 at the age of 20, he proved to be a problem. The documents paint a portrait of a volatile and, at times, dangerous inmate who threatened guards, fought with other inmates and disobeyed orders. He was written up at least 28 times on disciplinary charges that resulted in additional days on his original sentence -- infractions that resulted in him serving more than five years in solitary confinement. One of his more serious offenses occurred on September 17, 2005, when he threatened to kill a female guard, saying he would "kill her if he saw her on the streets and that he would make her beg for her life," according to the records. Over a two-year period also beginning in 2005, he threatened to kill two other prison guards as well as an inmate. In 2006, guards confiscated a letter Ebel wrote to a friend, another inmate at another prison, lamenting prison guards revoking his telephone privileges or turning off the water in the showers. "I just fantasize about catching them out on the bricks and subjecting them to vicious torture and eventual murder, and that seems to get me through the days with a good degree of my sanity remaining intact," he wrote. He signed it "Evil Evan Ebel Himself," adding an exclamation point with a swastika. A year later, in late 2007, Ebel wiggled out of his restraints and punched a prison guard in the face, according to the records. As part of a deal, he pleaded guilty in 2008 to assaulting a prison guard. The judge added four years to his sentence, which Ebel protested in open court. I just think four years is a little stiff, you know. By the time I get out, I'll be 33," he said, according to court transcripts. But somewhere between the judge's verbal sentence and a court clerk entering it into a computer, the order that Ebel serve the four additional years at the end of his current term rather than concurrent with it got lost. On January 28, at the age of 28, Ebel was released wearing an ankle monitor. Eluding authorities Every day, for 45 days, Ebel checked in with parole officers, one of a handful of conditions mandated by his release, said Timothy Hand, director of the state's Department of Corrections. He also followed the other conditions. He got a job. He found a place to live. He didn't violate an 8 p.m. to 6 a.m. curfew. He tested negative for drugs. He attended a drug treatment program. Then, on March 14, something went wrong. The "tamper alert" on his ankle monitor went off, according to parole records. Initially, the ankle monitor was listed "for repair" and a message was left for Ebel to make arrangements to get it fixed. He never called back. Three days later, on March 17, contractors overseeing the ankle monitoring system notified parole officials that Ebel failed to "make contact." It was the same day Leon left Domino's Pizza in Denver to make a delivery and never returned. His body was found later that day in a field near the suburban city of Golden, according to authorities. On March 19, parole officials went to Ebel's apartment to look for him. According to parole documents, it was evident from the state of the apartment that he left quickly or went into hiding to avoid arrest. That day, parole officials began the paperwork to return Ebel to prison. That night, Clements was gunned down as he answered the door of his home. Shootout in Texas A day later, on March 20, Ebel was speeding through Montague County, Texas, near the Oklahoma state line, about 700 miles from Monument. Deputy James Boyd tried to pull the car over for a traffic violation. The 1991 Cadillac Seville had two different license plates, according to an affidavit filed by the Texas Department of Public Safety's Ranger Division. The Cadillac had barely come to a stop when Ebel opened fire. "I remember seeing the gun shoot off," Boyd told CNN affiliate KMGH. I could see the cartridges fly out, at which point I blacked out. Boyd was hit twice in the chest and suffered a grazing wound to the head. He was saved by his bulletproof vest. "I got kind of halfway up looking for my mic," Boyd said. That's about the time I noticed, 'Hey I'm bleeding from the face. Something's not right. I need help.' The deputy radioed for help, and soon the law was chasing Ebel, who was barreling down the highway at speeds of up to 100 mph and firing wildly out the window of his car at the deputies in pursuit. The chase ended when Ebel careened into an 18-wheel truck as he tried to turn onto another road. With the front of his car crushed, Ebel got out and started shooting again. He didn't hit any officers this time. But they shot him, they said. Hours later, he was pronounced dead from a gunshot wound to the head. Ebel left behind telling clues in the wreckage of the Cadillac: a pizza box, pieces of a Domino's uniform, maps of Monument, handwritten directions and shell casings, according to court documents. The bullets that killed Clements, authorities later determined, came from the 9mm Smith and Wesson handgun taken from Ebel after the shootout. More questions Did Ebel kill the pizza deliveryman to get his uniform as part of an effort to disguise himself? Did he target Clements because of the prison chief's crackdown on white supremacist gangs in prison? Or was it something else? Colorado authorities have stopped short of saying Ebel acted alone in killing Clements and Nathan, raising the possibility of wider conspiracy. On Thursday, authorities announced two members of the 211 Crew were wanted in connection with the investigation into the killings. They refused to detail how James Franklin Lohr, 47, and Thomas James Guolee, 31, are related to the case. "Both men are members of the 211 Crew and are considered armed and dangerous; they have associated in the past with Evan Ebel," according to a statement released by Sheriff Terry Maketa of El Paso County, Colorado. Lohr was arrested Friday morning, Colorado Springs police said. Police had issued multiple misdemeanor warrants for his arrest, and it was not immediately clear if he will be facing new charges. The only other person charged in the case is 22-year-old Stevie Marie Vigil, who authorities accused of buying the gun used in the killings and giving it to Ebel, who could not purchase one legally because he was a convicted felon. To date, investigators have refused to detail the relationship between Vigil and Ebel. Finding answers One of the grief-stricken wives of the two men killed is tortured by the circumstances that apparently led to the shooting. For Katherine Leon, the widow with twin 4-year-olds, news that Ebel was released from prison early because of a clerical error is almost too much to bear. Outraged doesn't touch how I felt, it doesn't even touch, sick to my stomach, irate. How do you feel when something like this happens?" she told CNN. I mean, really, every day it's been getting worse. Every day I find something new out, and this was just the cherry on top of a really messed up month to say the least. Their question remains the same: Why did it have to happen? A portion of the answer may lie with a judge's warning to Ebel. "It's not too late for you to have a productive life," the judge said during Ebel's 2008 sentencing, according to transcripts, "but you're never going to make it on the outside with the attitude that you still have with you on the inside." Ebel didn't heed the warning. CNN's Carma Hassan, Ed Lavandera, Jim Spellman, Dana Ford, Piers Morgan, Anderson Cooper and Mark Morgenstein contributed to this report.