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CHAPTER 1 I’ll Free You, My Love

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The signal that the jailbreak could go ahead was a telegram. It arrived on the afternoon of Friday, 11 September 1970, while Dr Timothy Leary was exercising in the prison yard. He was called into the control office and handed a slip of yellow paper that read:

BELOVED—OPERATION TOMORROW

DOCTORS FEEL BEST NOT TO WAIT

TOTALLY OPTIMISTIC ABOUT SUCCESS

AND NEW LIFE DON’T WORRY I’LL BE

BRAVE WON’T BE DOWN TO VISIT

SUNDAY BUT WE’LL BE TOGETHER

SOON I AWAIT YOU I LOVE YOU

CONTACT ME AT THREE TREE

RECOVERY CENTER.

YOUR MATE

The sergeant who had handed him the telegram had done so with a look of sympathy. The message was from Tim’s wife Rosemary, and inmates always reacted badly to cancelled visits. Tim nodded and kept his face blank.

The telegram confirmed that arrangements for the necessary cars, drivers, safe houses and fake identity papers were complete, and that the ‘operation’ could go ahead the following night. The ‘three trees’ mentioned at the end of the telegram referred to the rendezvous. This was a group of trees, joined at the root, which stood a few hundred yards outside the penitentiary. If Tim could get himself outside the prison and reach the three trees, he would find a car waiting to take him to freedom. The symbolism was ideal, for Leary had Irish blood, and a group of three trees, always in fruit, was a symbol of unstoppable life in ancient Irish myths.

The stakes were high. If he did not reach the trees, there was little hope that he would ever be a free man. Leary had just been informed that he would be flown to Poughkeepsie in New York State the following week, where he would face further charges relating to the raid on his house in Millbrook nearly five years earlier. The likelihood of receiving more jail time was strong. This would destroy any hope that he had of escape, for this extra time would almost certainly trigger a transfer to a higher security prison. If he were to break out, it had to be Saturday or never. But that Friday the sky was a brilliant blue. His plan needed a foggy night in order to succeed. Without fog, there would be times during the escape that he would be silhouetted in the sights of the gun trucks and the armed guards. Without fog, only a miracle could prevent him from being shot.

He spent the following afternoon in the television room, watching the Stanford-Arkansas football game, and returned to his cell for the 4 p.m. head count. At 4.30 the whistle blew to signify the end of the count, and he waited for his cellmate to go to the food hall. Tim declined to join him, saying that he had eaten on the early line. The moment that his cellmate left, he got to work.1

He opened his locker. He removed the white laces from his sneakers and replaced them with dark ones. Then he sat down in front of the locker, a newspaper across his lap, and painted out the white stripes on his shoes and handball gloves with black dye. There was a sudden jangle of keys outside his cell door, and he quickly stuffed the shoes back in the locker. His heart was pounding as he sat motionless, listening to the guard move slowly away. By the time that it was safe to retrieve the shoes and return to work, he was sweating. He was rushing now, and his hands got covered in the dye. He wiped them on his handball gloves and shoved them back in the locker with the sneakers. Then he moved to the sink, where he began to scrub the black paint off his hands with a wire brush. He used his towel to mop the spilled paint off the floor in front of the locker. Finally, he hid the stained towel under his mattress.

There could be no going back now that his escape preparations were under way. He would not be able to explain why he had painted out the white on his gloves and shoes. He had crossed the line. He returned to his bunk and wrote what, at first glance, appears to have been an extraordinarily self-righteous farewell note to the guards. ‘In the name of the Father and the Mother and the Holy Ghost,’ it read, ‘Oh, Guards—I leave now for freedom. I pray that you will free yourselves. To hold man captive is a crime against humanity and a sin against God. Oh, Guards, you are criminals and sinners. Cut it loose. Be Free. Amen.’ Those who knew Leary well could recognize his sense of humour at work here, but everyone else could be forgiven for seeing only the arrogance and ego that so annoyed his enemies.

Tim then had to wait until after the next count, at 8.30, before he could make his move. Outside the sky was darkening and the weather was becoming cloudy. But there is a big difference between cloud and fog.

The thought of escape had been present when he was first imprisoned seven months earlier. During her very first visit, Rosemary had looked at Tim and made him a promise: ‘I’ll free you, my love.’

This was at Chino, a maximum security prison used as a holding centre for new prisoners. It was where convicts were evaluated and assigned to the most suitable prison to serve their time. It was here that Tim learnt about his potential future homes within the California prison system. Tehachapi, San Quentin and Folsom were all considered escape-proof. So was Vacaville, which was where the mentally disturbed were usually sent. It had a reputation for unpredictable maniacs and sudden violence, but it was not as feared as Soledad. Soledad was nicknamed ‘Gladiator School’, and was notorious for homosexual rape. The only options from which escape seemed possible were the forestry camps in the mountains, and the California Men’s Colony at San Luis Obispo. This was a minimum-to-medium security jail for professional and elite prisoners. But it seemed unlikely that he would be sent to either of these two facilities. These were options for quiet, uncontroversial prisoners, and, according to President Nixon, Timothy Leary was ‘the most dangerous man in America’.2

A factor in the choice of jail that he would be sent to was his status amongst the younger prisoners. The penitentiaries of California were notoriously brutal and violent. This was evident to Leary on his first night, when a burning mattress fell past his bars. It was accompanied by screams and shouts from convicts who were attempting to burn the jail to the ground while they were still locked inside.

New prisoners had to be quick to show allegiance to a particular clique or racial group, for a lone prisoner with no protection was seen as weak and vulnerable. When Leary arrived he was a hated figure in much of America. As one inmate told him, ‘If I had teenage kids and they were into drugs and I thought that you encouraged them, I’d have no hesitation in shooting you in cold blood.’ 3 This was a common attitude from the guards as well as many of the older cons. These were men who were on the wrong side of the generation gap, who often felt powerless to protect their children from the horrors of drugs and drug culture. And if there was one man who could be held responsible for the tsunami of drug use that swept the nation in the last years of the 1960s, it was Dr Timothy Leary.

Yet Leary was an untouchable figure in the prison system. This became apparent shortly after his arrival, when he intervened to stop the beating of a convict believed to be a snitch. Tim called for the guards, who rescued the man before he was seriously hurt. In doing so, he broke the cardinal rule of the jail—that of minding your own business. This should have earned him a beating, but the attack never came. Leary was protected by his status amongst the younger inmates. He was a living legend to prisoners in their early twenties and below, and especially to all those who had been involved in the drug culture. Drug use within the prison system was a long way removed from the idealistic, pacifist ideals of the flower children during the ‘Summer of Love’. Inmates would take whatever pills they could get, and those with a taste for amphetamines were unpredictable, violent and genuinely scary. It was immediately evident to the guards that, if he wished, Leary could wield his influence and cause a great deal of trouble, and a potential agitator is something that prison officers need to take very seriously.

So a move to the low-security penitentiary at San Luis Obispo, the California Men’s Colony West, did make some sense. The inmates here were older, white-collar prisoners, and the jail was regarded by many as a ‘country club’. The amount of time inmates were confined to their cells was kept to a minimum, and well-behaved prisoners were granted privileges such as contact with visitors or personal gardens. The convicts were aware that they had it good and that they had a lot to lose if they strayed from the conformist path, so they generally resigned themselves to doing their time peacefully. In case anyone was harbouring seditious plans, a semi-official ‘snitch’ system was in place involving certain prisoners reporting the inmates’ gossip to the officers in return for privileges. It was an ideal place to neutralise any potential Leary had for rocking the boat. And he was, after all, a 49-year-old academic and not some hardened street punk.

But was he an escape risk? San Luis Obispo was a low-security prison that did not usually take prisoners with long stretches to serve, as this placed them in a high-risk category. Tim had already been sentenced to a potential 20 years inside, and, for a man a few months short of his fiftieth birthday, this was a life sentence in all but name. It appeared that it would take something close to a miracle to put Tim in a low-security prison but, as Leary once explained, he was ‘in the miracle game’.

On his third day at Chino he was sent for the mandatory psychological assessment and presented with a set of tests. A significant part of these, he was shocked to realise, had been written by himself, 14 years earlier, when he had been one of America’s leading psychologists. They were known in psychological circles as ‘The Leary’. As he scanned the questions he knew exactly what personality traits they were assessing and measuring. He was able to answer each question in such a way that he would appear as close to a model prisoner as it is possible to get. The completed tests clearly showed, to the surprise of anyone who had read the newspapers during the previous decade, that Dr Timothy Leary was docile, conformist and meek. He was, the paperwork insisted, in no way an escape risk, and no one was prepared to argue with the paperwork. So the decision was made: Tim would be sent to San Luis Obispo.

The escape began at about ten to nine on the evening of Saturday, 12 September 1970. Tim put on his dark blue prison jacket and placed all his letters and treasured possessions in the pocket. He put on the blackened sneakers, left his farewell note in his locker and stepped out of his cell into the hallway.

Directly in front of him, at the end of the facing corridor, was the door to an internal prison yard. This was a square of grass enclosed on all sides by four cellblock corridors. It was also where a single tree grew, which seemed close enough to the corridor to enable getting onto the roof by climbing the tree and jumping across from its highest branches.

As he walked towards the door, a couple of convicts stood in the corridor and watched him pass. Tim had no choice but to walk past the prison yard door and round into another corridor, before turning back on himself and making another pass. The two cons were still watching. He walked past them again and headed into another cellblock. He was starting to act suspiciously now, he knew, but he had no option but to keep moving. He walked past them once again, and this time, once he had doubled back, they had gone.

He strode up to the door. As he was about to open it, he glanced into the adjacent cellblock where three more inmates were talking. One of them, a known snitch named Metcalf,4 looked up and glanced at him at the very moment he was about to reach for the door handle. Tim stopped himself and Metcalf seemed suspicious. Tim walked past and, after doubling back once more, found that when he reached the door again all three of the inmates were looking at him. There was no way that he was going to be able to get through that door unnoticed. He walked on.

There was another entrance to the yard, on the opposite side, but it was risky. He would have to walk across the floodlit square to reach the tree, and no one ever went in the yard after dark, not even the guards. But what choice did he have? He walked through this second door, into the light, and strode quickly and quietly across the yard, praying that no one glanced out of the windows of any of the four surrounding corridors. When he reached the tree he discovered that it was directly in front of the window facing Metcalf. There was no way he could climb up without being spotted. He ducked down and sat on the steps by the door, feeling very exposed, listening to the talk of the convicts a few feet away What was he to do? He knew that he couldn’t stay where he was for long. He would have to climb the tree and make a break for it. It would take Metcalf a few minutes to raise the alarm, so while climbing the tree offered only a small hope of success it was the only option that he had at that moment. He stood up, grabbed a branch and pulled himself up.

With impeccable timing, as Tim’s body appeared in front of the window, he saw Metcalf turn and face away from him. Tim shot up the tree and, within seconds, he had dropped down onto the slanted tiled roof of the cellblock. From here he could look down and see the guards lounging in the custody office. He removed his sneakers and padded barefoot along the corridor roof and across the cellblock, trying not to run into the television aerials that were nearly invisible in the dark. He could see into the neighbouring cellblocks and knew that their lights must be illuminating him up against the dark sky, but he was too elated to care. He reached the end of the cellblock and found his final obstacle: a telephone wire.

California Men’s Colony West was originally an old army base on the central Californian coast, just north of San Luis Obispo. It had been converted into a prison 16 years earlier, and consisted of rows of two-storey wooden barracks that had been connected by roofed-in walkways. It was, and is, considered a model prison, geared towards community work and rehabilitation, and at the time it did not suffer from the chronic overpopulation that has come to characterise the Californian prison system. There were flower beds and lawns, and uninterrupted views to the hills of the Pacific coast. There were no gun towers or walls, but gun trucks guarded the corners of the compound. Anyone attempting to climb the fence could be shot before they reached the top.

The jail offered regular, unmonitored contact visits, and Tim could spend hours with Rosemary every weekend. They could walk together through the gardens. This allowed Rosemary to pass LSD to her husband. It also allowed them to plan an escape.

Rosemary had organised a team of people who were prepared to get Tim out of America. There had been many obstacles to overcome. Once out of the prison, they would have to avoid the roadblocks that would appear across central California as soon as his absence was noticed. Tim would need to be moved to a safe house, and there were the matters of disguises and fake paperwork, and of finding a way to leave the country unnoticed. There was also the matter of the finance needed to fund the entire operation. It was not a simple task, but Rosemary was intelligent and determined, and Tim had legions of supporters who were more than willing to help. Assistance like this was a luxury that Tim did not have in his part of the operation. It was his job to find a way to get himself outside the jail without being shot.

Many options were considered while Rosemary made arrangements and the months passed. Tim studied the movement and timings of the guards and the gun trucks. He discreetly made enquiries amongst the few cons he felt he could trust. The simplest idea was to wait until the winter, when the thick sea fogs rolled in. Then he could simply climb the fence at the back of the compound under cover of the fog, and pray that he could slip unnoticed past the guards who patrolled the open land. But real, thick fogs were unpredictable, making it difficult to synchronise the escape with Rosemary’s preparations. It would also mean waiting until the middle of winter, which he had no intention of doing. Besides, he thought he had found another way: an escape route that could just work. There was a telephone wire that ran for 40 feet from the roof of the cellblock, across an internal road, and ended at a telephone pole that was on the far side of the fence. For weeks he studied it out of the corner of his gaze, wary of being caught looking too intently at any part of his route. He found that the best way to study it was during the yoga practice he performed daily in the yard, stretching his body into positions in which his half-closed eyes could look beyond the fence into the freedom beyond. He began playing handball in order to improve his physical fitness. And he waited for the signal from outside.

Tim crouched at the edge of the cellblock roof, looking down at the 20-foot drop below the cable. The height was crucial to his plans, as the cable was higher than the floodlights. This meant that on a reasonably foggy night he could pull himself across without being spotted by the guards or snipers watching the fence. But it also meant that it would take a lot of courage to launch himself away from the security of the roof, with nothing but faith and a thin wire between him and the ground below. He had been able to study this cable out of the window while sitting on the toilet, and felt sure that it could hold his weight. He would now put that belief to the test.

He put his sneakers and handball gloves on. Lying down on the edge of the roof with his head hanging over the drop, he clutched the wire in both hands and hooked his legs over it. Was it foggy enough? It was not a perfectly clear night, but there was more visibility than he would have liked. But there was nothing he could do about that, and from the moment he stepped out of his cellblock, turning back had not been an option. It was now time to risk everything. A fall could kill him, and if he was seen from this point on he would be shot on the spot. He tensed both hands and pulled himself away from the roof and out into the void beyond.

He had thought that the crossing would be short: a series of long, smooth pulls that would take no more than a couple of minutes. Instead, he found that a second telephone cable was suspended from the first, and the hoops that attached it every 10 inches or so got caught in his hands and feet. Swinging wildly, he struggled for every inch. After about 50 pulls he was exhausted, and physically couldn’t move any further. He was still no more than a third of the way across, hanging over the patrol road a good 20 yards from the fence. Leary hung on to the wire for dear life, sweating, panting and hurting, the 20-foot drop below seeming like an abyss. He was too old for this, he realised. It was just a month before his fiftieth birthday and his body simply wasn’t up to it. Why hadn’t he given up smoking, or worked out more? Was this why no one had ever escaped this way? Perhaps the wire had been placed there as a trap, as a joke by guards who were laughing at him even now through the scopes of their rifles? He glanced down and saw inmates sitting around in the TV room. Then he was lit up in a sudden glare of light.

A patrol car had appeared around the corner. He could see the blue of his denim sleeve turning yellow in the headlights. Slowly the car came towards him along the tarmac road. It passed underneath him. He looked down and could see the guard extinguishing a cigarette in the ashtray.

The car kept moving. He hadn’t been seen.

Then, from somewhere deep inside him, there erupted an enormous surge of energy. He was no longer thinking rationally, but his body was working, his arms and legs moving desperately. He was fixated on the fence. If he was shot, then he wanted to fall on the other side of the fence. At some point he was aware of his glasses falling away, but his limbs kept moving. ‘I wanted Errol Flynn,’ he later wrote, ‘and came out Harold Lloyd.’5 Then his fingertips touched the wood of the telephone pole. He grabbed the metal stakes at the top of the pole with both hands, before letting go of his legs and swinging down and around to the far side of the wood. It was a move he had practised many times on the end of his bunk. He half climbed, half slid down the pole and lay in the grass, still and panting, watching the lights of the prison that now lay behind the fence. The camp was quiet.

Then he spotted his spectacles glinting in the grass, lying just a few inches from the free side of the fence. He retrieved them and adjusted them on his nose with what he called his ‘funny professorial gesture’. For a moment he had regained the Errol Flynn-like composure that was an integral part of his mental rehearsals of this escape. Then he completely lost it again as he turned to walk quietly down the bank away from the fence, slipped on a stone and tumbled down amongst an avalanche of rocks.

He ran though the dark, listening out for patrols, following a route from memory that Rosemary had described to him. Walls of illuminated prison windows watched him disappear across the open land, run alongside a dry creek bed and follow a small ditch past the main prison gate. He ran past the sign that announced ‘California Men’s Colony—West Facility’, and found the railroad tracks alongside Highway 1.

Awareness of his new freedom hit home as he ran at full speed along the highway, stopping only to hide in bushes when headlamps signalled the approach of a passing car. This short sprint triggered an ecstatic, almost animalistic feeling. Despite his difficulty on the telephone wire, he was in good shape for a 49-year-old man. He was six feet tall, with a bouncy way of walking that made him seem taller and physically more imposing than he really was, and his slender build was more characteristic of a tennis coach than an academic. At the time of his arrest his hair was starting to turn grey, which accentuated the classical aspect of his features. But while his face was aristocratic, his mannerisms were restless and American, and his eyes and smile had an unmistakably Irish charm. It was this subtle Irish glimmer that overrode the American and classical aspects of his appearance and became the prominent characteristic in the memories of those who knew him. His reckless Irish streak could also be relied on to override the other elements of his personality at pivotal times in his life.

Moments later, he reached the three trees.

I Have America Surrounded

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