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