The Best American Crime Reporting 2008

Tad Friend: DEAN OF DEATH ROW

FROM The New Yorker

THOUGH LIEUTENANT VERNELL CRITTENDON had been reading Michael Morales’s mail and listening to his telephone calls for four months, he hadn’t formed much of an opinion of him by the evening of Morales’s scheduled execution. Crittendon, who had for sixteen years served as San Quentin State Prison’s spokesman-though his role at the prison was actually far more complicated-felt confident only of what he had set out to learn: that Morales had no wish to escape, assault his guards, or kill himself. After twenty-two quiet years on death row, the inmate with the startled brown eyes bore little apparent relation to the twenty-one-year-old thug, high on PCP, who had taken a car ride with a seventeen-year-old named Terri Winchell, bludgeoned her head twenty-three times with a claw hammer, raped her, stabbed her four times in the chest, and then took eleven dollars from her purse to buy beer and cigarettes.

At 10 P.M. on February 20, 2006, two hours before Morales was to receive a lethal injection, Crittendon, who has been the prison’s public face for all thirteen executions since capital punishment resumed in California, in 1992, made an unexpected appearance at the deathwatch cell. As Crittendon remembers it, the condemned man sat slumped on his mattress, awaiting what must come: the moment when he’d be told to put on fresh denims and a Chux incontinence pad, then marched into the death chamber and strapped to the gurneylike green chair. The spokesman, wearing a Livestrong bracelet and the black suit that he changed into for executions, gazed down at him without expression.

Ordinarily, Crittendon, an athletic man of fifty-three, is a model of affability. When he lopes through the prison, he teasingly greets passing guards and inmates-“Look out, now!” and “He ain’t playin’!”-then, when they stop him to register what are sometimes esoteric grievances, he responds with vigorous nods and says “Sheez!” and “Oh, my!” and usually promises a fix, proud of his ability to bend the most rigid of bureaucracies. As a frequent guest on talk shows like “Larry King Live,” Crittendon holds forth with relish on such topics as the crimes of death-row residents whose company the wife-killer Scott Peterson, recently arrived at San Quentin, might enjoy.

During an execution, though, his demeanor turns profoundly neutral. “Vernell has the hardest role,” the veteran guard John Gladson says. “He has to keep the victims’ families from being pissed off by not appearing too sympathetic to the condemned, but he also has to go back the next day and deal with the inmates on death row, who’ve all had their TVs tuned to Channel 5”-San Francisco’s CBS affiliate-“watching him like they’re reviewing a play.”

As Morales knew, his attorneys had convinced a U.S. District Court judge, Jeremy Fogel, that two of the three poisons he would receive could cause excruciating pain if the first one to enter his bloodstream, the barbiturate sodium thiopental, didn’t put him under. San Quentin’s execution logs indicate that, during six of the prison’s eleven lethal injections, the condemned may have been partly conscious; similar findings have led eight states to suspend use of the chemical mixture-sometimes called Texas Tea-employed in most of the death-penalty states, including California. To meet Judge Fogel’s concerns, the prison had brought in two anesthesiologists to monitor the procedure. But that night, when the anesthesiologists realized that if Morales regained consciousness they were expected to sedate him again, they told the warden that it would be medically unethical to do so.

Crittendon had just informed Terri Winchell’s family, who were in seclusion two hundred yards away, that the warden had postponed the execution for a few hours. He tried to radiate what he called “a veil of confidence: ‘Everything is moving forward, justice will be served.’” Then, projecting an attitude he terms “professional but sympathetic,” he says he told Morales of the delay, without explaining further. Morales dropped his face into his hands and said, “Oh, this is going to kill her family. They were prepared for it.”

“I was speechless,” Crittendon recalls. “I was just moved, for once. I’d never heard a statement of caring about the victim’s survivors from a death-row inmate.” After a slight pause, he told Morales, “I will make sure I keep you informed as this develops.”

At least, that’s how Crittendon related the event in conversations with me. But the execution team’s log shows that Crittendon never made a 10 P.M. visit, and that Morales didn’t learn of the delay until just after midnight. Crittendon acknowledged that his timetable must be off, but could provide no evidence to support his memory of the vivid exchange.

When Crittendon went to brief the press on the delay, he shifted his demeanor to appear “professional but indifferent to the eventual outcome.” Believing that the press would try to blame the Judge or the anesthesiologists for the setback, he blandly announced that the warden was going over “some additional training with some of the newer members that have just been added to our team.” Later, he returned to explain that “the warden has reached that level of comfort with all of the members on the execution team,” and they were just awaiting a ruling from the district court on a motion for a stay. Still later, he read a statement of withdrawal from the anesthesiologists, adding-rather at variance with the facts-that “this is a new problem.” Crittendon eventually announced that the prison would carry out the execution the following evening, using only sodium thiopental.

A single-drug injection had never been attempted, but Crittendon made the improvisation appear fitting and seemly, just as he had done with “citizens that were involved with civil disobedience” who had been arrested outside the East Gate; inmates “restricted to their assigned sleeping areas”-that is, locked down; and the condemned man expecting to partake of “the lethal cocktail.” (In the early nineties, when California used hydrocyanic gas, Crittendon spoke of a “team approach” that would “eventually end in a lethal environment.”) He excels at dispensing just enough information to satisfy reporters, and his sonorous locutions and forbearing gravity discourage further inquiry. Earlier, he had declared that Morales “was interacting with our staff in a very positive way,” and that the condemned man was suggesting that “this is not necessarily a sad affair.”

“To hear it from Vernell,” Kevin Fagan, a San Francisco Chronicle reporter who has covered seven executions, says, “everyone goes to his maker the same way: ‘calm, happily fed, and at peace with his fate.’”

CRITTENDON, WHO RETIRED IN DECEMBER, always sought to navigate a clean line through the acrimonious confusion surrounding the death penalty. The public broadly endorses the penalty-by about sixty-five per cent in most polls-but many capital cases are beset by doubt, mitigating circumstances, or evidence of the condemned’s remorse or redemption. California has a particularly thorough appellate process, and the result, on death row at San Quentin, is agonizing stasis: six hundred and twenty-nine men, the nation’s largest assembly of the condemned, now sit for an average of more than twenty-two years before their sentence is carried out.

Vernell Crittendon would seem to have been the ideal proxy for a citizenry that wished to see justice done but did not want to look too closely at its slow, and then suddenly swift, final workings. Yet Crittendon’s studied professionalism about executions that occur (or, mysteriously, don’t) behind stone walls late at night was greatly complicated by his role-largely unknown to the media or to inmates-in actually carrying them out. Though Crittendon was a mere lieutenant, he essentially ran the show-“the conductor of the orchestra” for executions, as one of the wardens he served under put it. Another warden says, “He trained everyone, he did everything, he choreographed it all.” Crittendon would often answer reporters’ procedural inquiries by saying, “I’ll have to check with the warden”-although he knew exactly what was going on because he had arranged it so, and was, in effect, serving as the spokesman for himself. “As long as you keep enough fire and smoke going,” he told me, “they don’t pay attention to the man behind the curtain.”

Crittendon wrote much of the prison’s lethal-injection manual, known as Procedure 770. At the weekly “special event” meetings in the warden’s office, he set the schedule for practice sessions by the execution team, for the inmate’s psychological evaluations, even for the tracing of the inmate’s veins to establish where the two I.V.s should go. The execution team itself was not in his purview, but he helped coördinate the prison’s Tactical and Investigative Services units, and selected and supervised a thirty-five-person Internal Security team who worked the night of an execution, evaluating them afterward for post-traumatic stress (a fairly common problem). Together with the prison’s litigation coördinator, he dealt with the state attorney general’s office about the progress of last-minute appeals. And he solicitously escorted the victims’ families to and from the prison-even as the officers he’d stationed outside the chamber were prepared to remove them if they caused a disturbance.

Crittendon would visit the condemned man at least once a week in the final months, studying him, under cover of bringing his mail and inquiring about his needs. As the prisoner was transferred from death row to a secluded cell under twenty-four-hour observation and, finally, to the deathwatch cell, he was weaned from the custody of officers he knew well to those he got to know briefly, to those, on the final evening, he didn’t know and never would. Crittendon took pains to insure that the emotional atmosphere around the condemned was gradually muffled as well, as if an institutional rheostat were being dimmed. “I tell everyone to keep your voice low, don’t laugh, and avoid all confrontation,” he said, adding that the soothing tone was “directed to the deserved outcome of getting the inmate to walk into the chamber without a struggle, hop up on the chair, lie still, and take the ultimate punishment.” Yet, he observed, “If they tell you pretty blondes in short miniskirts are going to put you to death, you’re still going to feel stress when you hear those keys jingling. When I’d take the condemned to the death-watch cell that evening, I’d see it hit them. All of a sudden, they’d walk with little steps, like when you tell a child, ‘Go to your room.’”

CRITTENDON LEARNED THE fate of Michael Morales the next day at 5:30 P.M., two hours before the rescheduled execution was to occur, when the warden told him that the prison would not be able, by the midnight deadline, to find a court-approved medical practitioner willing to inject Morales with an overdose of barbiturates. (Since that day, there has been a statewide stay of executions; in May, the California Department of Corrections and Rehabilitation, or C.D.C.R., announced that it would build a new lethal-injection chamber at San Quentin, and that it would overhaul staff training and tweak the chemical mixture to address Judge Fogel’s concerns.) After Crittendon told his staff, he went to the visiting room, where Morales was meeting with three of his lawyers. Crittendon approached their Plexiglas booth, turned to face Morales, and said, “I have been instructed to inform you that the warden is standing down from the execution.”

The lawyers stood in confusion. “What does that mean?” one lawyer asked, three times.

“He knows what that means,” Crittendon finally replied, indicating Morales with his chin. Then he turned away.

David Senior, one of the lawyers, recalls that Crittendon faced him rather than Morales, and says, “Vernell delivered the information in such a way-hands behind him, nose to a crack in the Plexiglas-that you could read zero personal feelings in it.”

When I told Crittendon that Senior had been struck by his detachment at the moment of reprieve, he said, sharply, “The moment I showed emotion, his attorneys would use it for their agenda, and my staff, who were also watching, would interpret that and they would allow their emotions to be seen, and then we are an embarrassment to the State of California.”

Every conversation between a guard and an inmate is circumscribed by tactical concerns. (You never give an inmate bad news when he’s not secured in his cell, or on a weekend, when fewer staff are on duty, and you never confide anything intimate; to be guilty of “overfamiliarity”-of a sympathy or engagement that prevents you from enforcing the rules-is an unforgivable lapse.) Still, Crittendon couldn’t help revisiting that exchange. Had Morales understood from the angling of the spokesman’s body that he was trying to speak only to him, to convey a kind of solidarity? Did he grasp the constraints the spokesman was under? “I was not able to have the kind of interaction with a human being I’d like,” Crittendon said. “I’d have wanted to sit down next to him, with no barrier between us.”

The morning after an execution, Crittendon was always at his desk by nine-right back at it, when some on the execution team would take a permitted five-day leave. Crittendon was such a “tower of strength,” as a former warden, Jeanne Wood-ford, puts it, that his colleagues were convinced that he both approved of capital punishment and shrugged off its impact. Yet immediately after an execution he would always linger until everyone had left and then sit in his truck in the deserted parking lot, thinking.

On the morning after the reprieve of Michael Morales, the prisoner was held in a stainless-steel shower stall on death row while guards returned his belongings to his regular cell. He was visited by Eric Messick, Crittendon’s deputy, who knew that he would have to answer questions about Morales’s state of mind. Messick, who is as direct and artless as Crittendon is strategic, asked Morales how he was doing.

“A lot better than yesterday,” Morales said.

“So now you’re just like the rest of us,” Messick said. Morales looked up quizzically, and Messick said, “Now you don’t know when you’re going to die, either.”

Morales thought that over, smiling a little, then said, “Yeah, but this is not finished.” Still, he was touched by the visit, saying later, “They’re usually very concerned that you’re doing fine before they kill you-not after they don’t kill you.”

WHEN YOU PASS through the sally port at San Quentin, you feel as if you’d walked into an old Warner Bros. prison movie, the kind where Jimmy Cagney rattles his cage. Built in 1852, during the Gold Rush, this barrow of crumbling granite on the former Bay of Skulls has held Black Bart, Caryl Chessman, Sirhan Sirhan, Charles Manson, and Richard (the Night Stalker) Ramirez, among many others, and the ferocity of their hatreds seems to linger in the air.

Steven Ornoski, who was warden during the Morales matter, calls it “the worst prison in the California system: it’s old, filthy, noisy, poorly laid out, and understaffed. I told people I’d been dropped on the Titanic-after it had hit the iceberg.” When a federal health-care receiver visited San Quentin last spring, he found that its emergency room had lacked gauze and sutures for four months.

From 2004 to 2006, San Quentin was run by a bewildering procession of nine wardens and might well have been closed, had there been somewhere for its occupants to go. California’s thirty-three prisons hold a hundred and seventy-three thousand inmates, twice as many as they were built for. Nineteen thousand inmates now sleep in hallways and gyms, and Governor Arnold Schwarzenegger recently classified the prisons as being in a state of emergency. The system’s faulty health care has been blamed for one inmate death per week, and a state law requiring that prisoners be brought to a ninth-grade reading level by the time they’re paroled is basically ignored. Sixty-six percent of California’s released inmates return to prison within three years, twice the national average, but rehabilitation programs are nearly nonexistent: most prisoners are never introduced to anything more remedial than a barbell.

On this conveyor belt to nowhere, San Quentin is the only California prison with both accredited high-school and college programs; four hundred and fifty pass-holding volunteers from the Bay Area regularly instruct its inmates in everything from Hooked on Phonics to yoga. In a deeply conservative environment-the vast majority of the thousand guards who work in the prison grumble about “Camp San Quentin” and “hug a thug” mollycoddling-the flourishing of these programs is almost unaccountable.

They owe their survival, in large part, to Vernell Crittendon. As wardens cycled through, Crittendon became the institution’s memory, conscience, and consigliere; the duties he took on included everything from organizing inmate walkathons for charity to running the prison museum. “Vernell seemed to know everyone in the whole United States,” Jill Brown, a recent warden, said, “and which exact person to go to to help the prison-from who to call at the Mexican consulate to who to contact among Louis Farrakhan’s people if there was an issue in our Muslim community. He was Mr. San Quentin.”

Crittendon led many lives at the prison. Early in his career, he became widely known and feared as a member of the prison’s “goon squad”-a buccaneering unit that beat down prisoners to gain compliance. But in the years after he was promoted to the administrative staff, in 1988, he began to trade upon that reputation in order to rehabilitate the men whose heads he had so often pummelled. It was a delicate balancing act; nearly every time he made a decision, either the guards or the inmates would complain that he was favoring the other side. Even as he publicly lauded the prison’s punitive strictures, he privately began to encourage a multiracial group of inmate leaders to quit “the game”: he’d ask about their families, allow them to make off-hours phone calls to their children, introduce them to reporters as “our success stories,” even organize memorial services for their cellmates. Felix Lucero, a lifer, said, “You always want to feel you can be rehabilitated, that you’re not an animal, and Crittendon makes you feel that way. He treated me like we were sort of…friends.”

Crittendon helped oversee inmate self-help programs like No More Tears and the Vietnam Veterans Group, and was an adviser to many others. Every other Friday, as the centerpiece of a program called Real Choices, which tries to set wayward urban kids on responsible paths, he would escort a group of ten-to-eighteen-year-olds into the prison to meet lifers, who tried to talk-or shout-some sense into them. Crittendon, who is married to a nurse and has a fifteen-year-old son, inaugurated Real Choices in 2001, but, characteristically, he encouraged the inmates to speak of the program as their own creation. Once, he had hoped to become warden himself, but as warden after warden fell to internal politics within the C.D.C.R. he came to understand the uses of stealth. When he publicly declared that the Crips gang co-founder Stanley Tookie Williams-one of the prison’s most famous inmates-was a con man whose later good works were intended solely to avoid execution, he lost the trust of many inmates he’d so carefully cultivated. The Williams matter nags at Crittendon still.

Crittendon’s approval, on the other hand, can open doors. Of the fifteen lifers he originally used in Real Choices, four have been paroled, an unusually high percentage. Crittendon had written to the Board of Parole Hearings on those inmates’ behalf because each met his five criteria: being responsible while at San Quentin; pursuing an education; serving as a volunteer; having a solid support system on the outside; and believing in God or a higher power. He asked Jerry Dean Stipe, a bearded Vietnam veteran known as Wolf, to be a co-founder of Real Choices-yet he didn’t write a letter for Stipe, he told me, “because he was an atheist.” Crittendon said, “Without a belief in something larger than yourself, you backslide. I don’t help the men to be a nice guy or to make them into nice guys. The inmate’s going to benefit from being rehabilitated, but it’s really about protecting the decent people out in society who he’d victimize.”

I SPOKE TO CRITTENDON over a number of months. Whenever I joined him at one of the Denny’s or Chevy’s restaurants where he suggested we meet, he always sat in the back, facing the door. Before venturing an observation, he invariably paused, making rapid calculations about message, diction, tone of voice, and the likelihood of being misinterpreted. It was of a piece with how he never attended guards’ barbecues, never let anyone get in back of him or see him off duty. “I can’t be effective with each camp in the prison if they know everything about me,” he said. “Vernell’s world is a lot neater and more controlled that way.”

Crittendon’s ability to shift among lingoes and affects is a common prison adaptation. But his speed is astonishing: he’s like an actor who glides offstage in a tuxedo, pops his head out in an Indian headdress, and then shambles from the wings in a bear suit. When he was accompanying two clergymen out of the prison last year, Crittendon mentioned that a middle-aged lifer they’d met had been the first juvenile in San Francisco to be sentenced as an adult. “He has not even had the luxury of-the privilege of-knowing a woman,” Crittendon told them. While amending his word choice, he deepened his timbre, so that what began as a salacious aside sounded, by “knowing a woman,” almost Biblical. Yet Crittendon’s ingratiating reserve helped prevent him from becoming just another guard. “Our training is not designed to broaden an officer’s mind,” Mike Jimenez, the president of the state’s correctional officers’ union, says, with regret. “Everyone wants to be seen as the meanest, craziest officer, because then no one screws with you. It’s dog psychology.”

One of Crittendon’s many duties was conducting on-the-job training on such topics as “Gangs,” “Drugs,” and “Application of Restraint Gear.” One morning last summer, Crittendon was giving a “Use of Force” class for twenty officers in a trailer behind the prison. “O.K., you’re in reception and an arriving criminal refuses to give you a DNA sample,” he said. He hopped to the side and played the inmate, strutting and pimp-rolling: “You ain’t stickin’ nothin’ in this mouth, nohow.” Then he shifted back. “You say, ‘O.K., Jack, you can either give us a DNA sample from your mouth or we’ll collect it as it leaks out of your nose.’” There were appreciative chuckles. “What gives you the right to say that? Because you are gaining compliance with a lawful order. But if some knucklehead says”-side step-“‘I ain’t gettin’ out the shower yet, dawg, I gots soap on me,’ can you use force? No, because you do not have a lawful order requiring you to effect the removal.” He smiled, slowly. “When I came here, in the seventies, that inmate would have been touching every fixed position, every wall, post, and floor, all the way to Ad Seg”-Administrative Segregation, more commonly known as the Hole.

Crittendon arrived at San Quentin in 1977, at age twenty-three, having worked previously as a police cadet and a security guard in San Francisco. San Quentin at the time was a maximum-security prison, housing the most violent criminals. (It’s now a medium-security facility.) In the early eighties, the prison reported three felonies a day, bloody incidents with spears and match bombs and blow darts and zip guns, not to mention routine “gassings”-cups of fermented urine and feces hurled in a guard’s face. San Quentin recruited Crittendon as part of a belated effort to integrate a heavily white officer corps that gave the prison the feel of a plantation. Crittendon saw a prison run by “the Europeans”-“white guys who were not going to give the others a piece of the pie.” Though his own father had deserted his family when Crittendon was twelve, and though he would eventually come to see himself as a role model for black inmates who had grown up in similar circumstances, he soon found himself reluctantly beating up black prisoners-and only black prisoners-on white lieutenants’ orders. Even today, the prison both reflects and accentuates the broader racial divide: blacks are six times more likely to be incarcerated than whites, and once at San Quentin (and most prisons) they are housed with other blacks, on the theory that segregation reduces racial tension. The golden rule at the prison, according to an officer named Jeff Evans, is “You hang with your own.”

In his class, Crittendon, who while on duty shot more than twenty men, none fatally, began explaining the complex algorithm that permits the use of deadly force: essentially, an imminent threat of death or severe injury. “Now, this is the scary part-God willing it doesn’t happen,” he said. “Say this C.O.”-correctional officer-“comes back on the block and his son just got killed by some criminal and he pulls out a nine-millimetre and starts firing into the cells-boom! boom! boom!-taking the inmates out.” Crittendon was pointing an imaginary pistol at the officers, mowing them down. “What do you do?”

“Wait till he runs out of bullets,” someone said, and everyone cracked up.

Crittendon threw his head back to guffaw, but instantly stopped. “That was a joke,” he said. “You do have to shoot him, because otherwise the inmates’ families will sue you. You have that responsibility.”

ONE AFTERNOON, a female San Quentin employee approached Crittendon as he was guiding some visitors around the prison museum and asked him to show her the execution chamber. In 1967, the chamber was shut down at the beginning of a series of constitutional challenges to the death penalty; since 1992, when it reopened, it has been in regular use, starting with the death by gas of Robert Alton Harris, who had shot and killed two teenage boys and then eaten their Jack in the Box hamburgers.

“Sure,” Crittendon said to the woman. “Let’s go.”

“Oh, neato! What’s it like?”

“It’s a gas!” Cackling, he led her just south of the prison’s main entrance and unlocked an iron gateway to a narrow courtyard. It was here, early on April 21, 1992, that witnesses assembled to observe the Harris execution. Crittendon, who had been placed in charge of the prison’s programs by Warden Daniel Vasquez four years earlier, was by then the prison’s spokesman, and Vasquez had told him how to publicize the event: “Don’t personalize it, don’t dramatize it, don’t embarrass the Department of Corrections, don’t embarrass me, don’t embarrass yourself.”

Crittendon also had significant responsibility for discharging the execution, and he recalls having “a whole sense of anticipation as the plan I had helped to create was unfolding.” That final evening, he oversaw Harris’s last meal: “He’d asked for pizza, and I directed that it be Tombstone Pizza-”

Tombstone? “I have a sick side of me, I guess-my own little personality thing,” Crittendon said. “He put a whole piece in his mouth and he says, ‘Critter, you want some?’ But it wouldn’t have been appropriate.”

Crittendon had created a meticulous timetable, but it fell apart as the courts issued four separate stays, the last called in when Harris was already strapped in the chair. As the Supreme Court was preparing to vacate the final stay, Vasquez, under heavy pressure from the attorney general’s office, told Crittendon to get the witnesses back as soon as he gave the word. “He gave the word at 6 A.M., and by 6:05 all the witnesses were entering the chamber,” Crittendon says. Vasquez recalls, “There was a haste, an urgency to get it all done that to this day is a source of shame to me.”

As the final witnesses passed through the courtyard Crittendon made a gesture that two witnesses remember as an excited fist pump. One describes Crittendon’s gesture as “distinctly celebratory”; another, Michael Kroll, says, “Crittendon raised his fist in the air three times, as if his team had just scored a touchdown. To win, for him, was to get this done.”

Crittendon said he doesn’t recall making any gesture of overt triumph and that he could have been giving a “move ’em on up” signal to a driver who had witnesses waiting in a van. When I reminded him that the witnesses had already assembled in the courtyard, he said that he might have been beckoning to the “extraction team” to stand ready to remove Harris’s brother if he caused a disturbance, as Crittendon had heard he might. In the event, Harris’s brother watched in silence as the condemned man gasped and convulsed and turned blue before being pronounced dead, ten minutes later. (In 1994, U.S. District Court Judge Marilyn Patel banned gas as the state’s preferred method of capital punishment, declaring it cruel and unusual. After some notorious executions, including two in Florida in the nineteen-nineties in which the electrocuted man’s head burst into flames, thirty-seven of the thirty-eight death-penalty states use lethal injection as the primary method; only Nebraska still relies on electrocution.)

Now, after unlocking a door in the prison wall, Crittendon gave a ringmaster’s flourish: “The execution chamber.” We stepped into an airless room dominated by a squat green apparatus that resembled a bathysphere. The woman employee circled it, peering at the iron doors, the thick windows, and the flat green chair within. As Crittendon watched her, his face took on a stoical, almost sorrowful cast. “The inmate who did that welding, in 1937, Alfred Wells,” he remarked, “was back inside six years later for three murders, and he died right here in the chamber he built. ‘I fought the law and the law won’-bada bing, bada bam.”

“When’s the next one?” the woman asked. Crittendon explained the stay, and when she asked his opinion of the death penalty he parried coolly, “There are those who raise the argument-as is their absolute right-that you should not have state-sanctioned killing, even though the public supports it. One will see how it all plays out.”

Executioners seek to maintain their detachment, but they often begin to feel empathy or depression. John Robert Radclive said that visions of the prisoners he hanged between 1892 and 1910 “haunt me and taunt me until I am nearly crazy,” and Amos Squire, the doctor at Sing Sing who between 1914 and 1925 sat beside the condemned during a hundred and thirty-eight electrocutions, wrote that he finally quit when, after signalling for the procedure to commence, he began to feel “a sudden, terrifying urge to rush forward and take hold of the man in the chair, while the current was on.”

Crittendon’s mother, Louise, always scrutinized him after an execution; she felt that each killing hardened her son a bit, but, she told me, “it didn’t take root in him.” Yet Crittendon told me that he has come to believe that lethal injection is inhumane-to the executioner. “You are eye to eye with the inmate as you have skin-to-skin touch, smelling his body odor, feeling his breath, and this is someone who has been in your care at the institution, usually without being violent, for at least fifteen years,” he said. “So transference occurs. I’m the only person who was there for all eleven of the lethal injections, and every single one of them I cannot forget-I close my eyes and I can see and hear it.”

ON DECEMBER 12, 2005, the night of Stanley Tookie Williams’s scheduled execution, a crowd began gathering early outside San Quentin’s East Gate and soon numbered about a thousand. Williams, widely known for building one of the country’s most notorious street gangs, had become even more famous for his prison transformation: he was the most prominent cause célèbre for death-penalty abolitionists since Caryl Chessman, the charming serial rapist and author who, after twelve years in San Quentin, went to the gas chamber in 1960. Williams had been visited by such celebrities as Snoop Dogg and Jamie Foxx (who played Williams in a television movie, “Redemption”), and the crowd outside that night included Jesse Jackson and Joan Baez, who sang “Swing Low, Sweet Chariot.”

At 7:20 P.M., Vernell Crittendon approached the deathwatch cell with mail and a pitcher of water. Williams, a barrel-chested man with gray cornrows, was seated on his mattress as if it were a throne. He had declined a last meal, a sedative, and the chance to vouchsafe his last words to the warden. The two men, born just days apart to absconding fathers and stern, religious mothers, stared at each other through the bars. Even then, Williams believed that the courts or the governor would intervene. “I brought the mail,” Crittendon said at last.

“Fine. Send it to Barbara,” Williams said, referring to Barbara Becnel, a community-services activist and his most loyal supporter. He would not take the water or speak again. A week earlier, Williams had told Crittendon, “I don’t even want to talk to you-you’re one of the people trying to get me executed.” He had asked a captain to stop Crittendon from bringing his mail, and told the warden that he didn’t want the spokesman present during discussions about the schedule.

In the years after Williams came to San Quentin, in 1981, convicted of four murders, Crittendon said that he would chat with him about black pride. “I’d play the race card,” he recalls, “saying, ‘How come that white officer can go down to talk to that skinhead, and you see me as an enemy-and yet we’re brothers, and your whole thing is black pride?’” The talks can’t have been very convivial, as Williams not only hated cops, whites, and almost everyone-as he demonstrated by repeatedly attacking other prisoners-but had no use for Crittendon, whom he referred to as an “Uncle Tom” and “Mr. Lickspittle.”

But beginning in 1993, after what he described as a gradual spiritual awakening, Williams stopped fighting and began to apologize for his past. An autodidact with a fondness for words such as “braggadocio” and “anent,” he went on to co-write, with Barbara Becnel, nine children’s books decrying the gangster life style. Becnel says, “Vernell was very helpful at first. Stan was in the Hole and couldn’t get phone calls, and Vernell would maneuver and break the rules and allow us to speak on the phone.”

Crittendon says he secretly hoped that Becnel would help him to persuade Williams to renounce the Crips and name his accomplices in the murders-crimes that Williams insisted he didn’t commit-and to do it on television. (Becnel and Crittendon agree that he never broached any of those topics with her.) As Crittendon recalls it, in the mid-nineties Williams finally responded to the last of a series of invitations Crittendon made to him to unburden himself on Larry King’s program: “A man don’t rat,” Williams said. “And I’m a man.” Crittendon says that he realized then that Williams was just a hustler who would never quit the game. “If I could have got him, that would have been great! Not for Vernell,” he quickly clarified, “but for public safety.”

However, in notes that Williams typed before meeting one of his lawyers in 2005, he scorned the idea that he and Crittendon had once had a promising relationship, noting that in twenty-four years in San Quentin “there was never a reason for him and I to speak at length.” Becnel believes the turning point for Crittendon occurred in 2000, when Williams, who had helped broker a gang truce in Los Angeles over the telephone (and would later broker another truce in Newark), was nominated for the Nobel Peace Prize. Peter Fleming, Jr., one of Williams’s lawyers, told me, “The clear sense I had with Vernell was ‘This convicted murderer’s getting all this attention-why am I not getting it?’”

Certainly Crittendon took the case personally. Beginning in 2004, after Williams’s appeals had been exhausted, Crittendon waged a largely clandestine media campaign against the inmate. (He first sought and received approval for his efforts to “correct public misimpressions” from the state attorney general’s office and the C.D.C.R. spokesman in Sacramento, who himself acted as liaison to the governor’s office, which would have to rule on Williams’s petition for clemency.) Crittendon’s démarche was usually accomplished through quiet suggestion: Rita Cosby, who conducted the last television interview with Williams on her MSNBC talk show, says, “Vernell’s appraisal caused me to be more skeptical, and gave me some questions to ask Tookie: was he still involved in organizing gang activity behind bars?”

A month before Williams’s scheduled execution, Crittendon gave an interview to the Associated Press in which he said of Williams, “I just don’t know that his heart is changed,” and suggested that Williams was still orchestrating gangland activities. This was an unprecedented attack for a prison spokesman to make. “To turn public opinion in favor of executing Tookie Williams was not just weird-Tookie simply minded his own business-it was wrong,” the former warden Daniel Vasquez told me. “Vernell may have gotten addicted to his own image of what he could do.”

Crittendon’s observations carried weight because he represented a government authority and because reporters liked and trusted him. But those observations seem to have derived more from the spokesman’s animus than from the inmate’s misconduct. Crittendon had told the A.P. that Williams’s prison bank account was suspiciously large, but there was only sixteen hundred and eighty-two dollars in it. Crittendon had found it troubling that Williams was not counselling his son, Stanley IV, a former gang member in prison for murder, but he acknowledged to me that he checked Williams’s mail only in the final month or so-and hadn’t read Williams’s autobiography, in which he details his extensive correspondence with and counselling of his son-“so I can’t say for sure he wasn’t writing his son.” When asked whether he now considered his campaign unusual or unwarranted, Crittendon said it “was approved through the department” and “an appropriate response to the questions that were asked by the media.” Yet he also eventually acknowledged that Williams hadn’t actually been orchestrating gangland crimes. The spokesman’s problem, then, was that Williams’s ongoing defiance of Crittendon-and the system that Crittendon had come to embody-made him a living symbol of the Crip life style.

At eight-thirty that night, Crittendon slipped off to the staff rest room in the prison’s abandoned schoolhouse, as he always did on the eve of an execution, to change into his black suit and then sit and think about the condemned man. Crittendon often began to empathize-but not this time. “I was thinking how the gang Stanley created had destroyed the African-American community,” he recalls, “how you can shoot someone on the corner in broad daylight and no one who sees it will say anything, because they fear the Crips.”

At midnight, Crittendon took up his customary post in the death chamber, facing the window at the foot of the green chair, “directly across from Williams’s head, so that I could look right up his nostrils. It was part of my duties to watch, because if we have a blowout and a vein starts spurting blood I have to escort the witnesses out.” As thirty-nine witnesses looked on in increasingly tense silence, a nurse repeatedly tried to establish the standard backup I.V. in the convict’s left arm as Williams seethed and finally made an impatient remark. When the nurse exited, after twelve minutes, the second I.V. still wasn’t in, but Warden Ornoski, not realizing this and having found the delay excruciating, said, “Proceed.” The chemicals began to flow into Williams’s right arm.

“I always wanted to be able to see the moment when the life had left the person,” Crittendon said. “Stanley went motionless pretty quickly, consistent with what you’d expect. Whereas with Manny Babbitt”-a murderer executed in 1999-“you could see a tightening in his throat, little shivers and twitches when he felt it coming on.” Crittendon demonstrated, jerking his head rapidly to the side and grimacing. “Stephen Wayne Anderson”-a prison escapee and murderer who was executed in 2002-“was looking around and saying ‘I love you! I love you!’ to his loved ones, then he laid his head back and to the side, and I could see, Oh, he’s gone. But you’re under such scrutiny there’s not time for emotions. The sniper, when he fires off that shot, there’s not time to think, I just took a human life. No, he’s got to sight on another target before someone fires at him.”

Barbara Becnel, who felt that she had just seen a prolonged “torture-murder,” whispered a suggestion to two of the other witnesses, and as they left the chamber they cried, in unison, “The State of California just killed an innocent man!” Shirley Neal, a Williams supporter, happened to look at Crittendon at that moment, and she recalls that “he looked shocked and frightened.” Crittendon says that he was merely surprised by the outburst, and that no personal reflections entered into it. Indeed, he says that his efforts to discredit the condemned man were unrelated to the failure of their relationship: “My goal was never to reach and change Stanley. He was just a tool for me to have an impact. If you pick up a cup and it’s all dirty, do you worry about why it’s all dirty, or do you pick up another cup and quench your thirst? I put the dirty cup down and quenched my thirst.”

ONE MORNING IN JUNE OF 2006, Crittendon introduced me to Lonnie Morris, a lean black lifer he has known for more than a quarter century. It was the day before Morris and a handful of other star inmates would be the subjects of a two-part series on “Larry King Live,” taped in the prison’s courtyard. “You’ve got to educate tomorrow, man,” Crittendon told Morris. “The public lives in generalities and paranoia, where you’re the bogeyman.”

Just before the taping, Crittendon gathered the inmates in the chapel for a briefing. He predicted, accurately, the topics that King would raise-including drugs and violence-and explained that the inmates didn’t have to address them. “This is not about you,” Crittendon said. “It’s about the millions of incarcerated men you represent-speak for them.” The inmates stayed tenaciously on message. When King asked “What about rape dangers, male to male?” Morris said, “Honestly, you’re going to find in prison the same thing you find in society,” and then began talking about the Real Choices program.

Many of the guards were upset that Crittendon had given murderers a national platform, and that the inmates were being taped in front of a memorial to eleven San Quentin employees killed in the line of duty. The next day, as it happened, Crittendon was the master of ceremonies at the rededication of the memorial, and he made sure he was seen scolding Morris for shaking my hand “on the day for honoring our dead.” “Vernell wears a lot of hats,” Morris told me, wryly. “If he’s walking through with the warden, wearing his ‘safety and security of the institution’ hat, I’ll just keep stepping by.”

That same month, a new warden, Robert Ayers, Jr., took over at San Quentin, and his prison policy emphasized safety and order rather than rehabilitation. Crittendon decided to retire in December, four months short of thirty years; his deputy, Eric Messick, replaced him as the prison’s spokesman, but the innumerable other duties that Crittendon had assumed over the years were absorbed-or sloughed off-by the system. His role in executions will be divided among a number of officers, who will be guided not by a protean expert in avoiding embarrassment but by written procedures. Two weeks after Crittendon retired, Ayers banned visitors from the cellblocks, long a staple of Crittendon’s tours; he has since won praise from officers-and aroused concern in inmates-by putting an end to all Crittendon-style shortcuts and unilateralism. Ayers declined to talk about Crittendon or his legacy, but observed, “If you just pick which rules you want to follow, the prison is a very capricious place.”

IN MARCH, VERNELL CRITTENDON visited San Francisco’s Tenderloin Community School to give a Real Choices briefing to a group of fourth and fifth graders, many of whom he would soon take on a tour of the prison. Crittendon, who by then was three months retired and contemplating an eventual run for the Contra Costa County Board of Supervisors, was wearing a black San Quentin polo shirt, a black San Quentin warmup jacket, and a ring with a tiny image of San Quentin that an inmate had made for him in metal shop. But the twenty kids he met with in a basement classroom were not intimidated by the visible tokens of incarceration. And when Crittendon tried to impress them with the importance of choosing their friends wisely, catcalls filled the air. “We’ll wait for these gentlemen to finish,” he said evenly.

Crittendon had brought two ex-cons with him. One of them, Michael Tomlinson, a drug dealer turned pastor who was wearing a jogging suit that covered white-supremacist tattoos, took the floor and said, “There’s no tough guys in the room-you’re not tough.”

“You ain’t tough,” a boy named Tyrell, who had long cornrows and was slouched in his chair, replied.

“There’s no one so tough the Man can’t beat him down,” Tomlinson said, and the bleak authority in his voice silenced the room.

Afterward, heading out, Crittendon found himself in the school’s vestibule, and remarked, “Just like a prison-the sally port.” We went across the street to a Peet’s coffeehouse, where he said that the kids wouldn’t listen to him, a policeman, and that his real role was to introduce the ex-cons. “The principal would never say, ‘Come on in, Michael T., drug taker and drug dealer, killer of blacks, and talk to our kids.’ I vouch for Michael, now that he’s a pastor-but I never want to forget that he’s a bad guy.” Crittendon likes to say that he doesn’t judge someone by a single bad deed, but neither does he judge someone by ten years of good deeds. “The best analogy I can think of-and this is definitely the way I thought about Stanley Williams-is the circus,” he said. “You know how you see a five-foot-eight balding man with a potbelly walk into the lion’s cage and snap his whip, and the lion rolls over and grovels in the dirt? You put that lion back in the jungle, and if that same man walks down a bushy path he becomes lion lunch. I will always be friendly to former inmates, but I won’t be friends.”

The conversation turned again to the executions. He’d been thinking about Manny Babbitt’s, in 1999. “That always stood out in my mind,” he said. “A war hero who saved a guy’s life in Vietnam by diving on a grenade, an African-American, and it appeared that his crime centered on post-traumatic-stress syndrome-he sexually assaulted and murdered this woman, then tied a toe tag on her body, like they did in Vietnam. When I spoke with Manny in the deathwatch cell, he stood at attention three inches from the bars and always said, ‘Sir, yes sir!’ His brother had turned him in with the caveat that the detectives would help him and not seek the death penalty, and here I was standing with his brother, watching him be executed.” Crittendon stirred his espresso. “My dad’s brother was in Vietnam, and he came back with a lot of psychological problems, and he-he ended his life early by his own hand. It connected with my life experience. I didn’t go around saying, ‘Poor Manny,’ but it was what I was thinking. You’ve got to make sense of this thing.”

Did he ever?

“I left it in God’s hands. There must be a purpose in the Lord putting me where He did, even though I would never have chosen for my legacy ‘He put to death people who grew up in terrible, deprived circumstances and didn’t have much chance.’ When I move in black communities, the very first thing people say to me is ‘You really handled your business well up there on TV-you were impartial.’ So I’ve shown we can do it. I was the face and the voice of a major organization. I broke down Europeans’ stereo-types-the articulate black man. Maybe,” he said, slowly, “maybe it’s not that these lives were just sacrificed but that there was a greater good to my being able to serve as a role model on those very public occasions. But there’s all these layers on top of layers,” he continued. “Because if they were to tell me tomorrow, ‘Vernell, there will be no more executions in the state of California,’ Vernell would not be sad.”

TAD FRIEND is a staff writer at The New Yorker, where he writes the magazine’s “Letter from California.” He is at work on a family memoir.

Coda

This story held my attention because I like sorting through ambiguity, and Vernell Crittendon is extremely complicated. So are the people he dealt with. During my reporting I attended some of the college classes taught inside the prison, and one evening, during a break, I spoke with Louis Branch, Jr., a courtly-seeming black man. Branch had a history of sex crimes and was serving a life sentence, but he was a diligent student. When I asked him about Crittendon-who, concerned about Branch being near young, trusting female volunteers, had unsuccessfully sought to persuade the program’s director to bar him from the classroom-the inmate picked up his pen. “Vernell Crittendon is very active in giving us a plethora of chances to improve ourselves,” he said, as he wrote on a piece of foolscap. “That’s the success side. The failure side is the philosophy of revenge. Why not challenge Tookie’s compassion, challenge him to live up to Vernell’s philosophy of restorative justice, of giving back? What would we have to lose? Our hate, our violence. That’s all.” He showed me the sentence he’d written: “Vernell Crittendon is a prisoner of the penal system, as we all are.” Several months later, Branch was committed to the prison’s Adjustment Center for allegedly trying to overpower a nurse. He subsequently earned more time in solitary for trying to seize a guard through the slot in his cell door.