Captain Jack Harkness knew pain. He knew dull, endless aches and sharp, excruciating agony. He knew pain that felt it would never stop, and pain that felt like it would succeed where nothing before had, and finally kill him.

Yes, Captain Jack Harkness knew pain, and he knew better than most that the worst type of pain wasn't physical. It was missing someone so much you thought your heart would physically break in two, it was wanting to curl up in a ball and sob for hours because of the betrayal,  and the sheer pain. And more than that; it was the complete and utter loss of hope.

Captain Jack Harkness knew pain, but what he didn't know was why this branch of physical torture hurt quite so much.
He had been tortured before, multiple times, and hell, once or twice he'd even done the torturing. He'd been killed numerous times, too: a  stray javelin, gunshots, poison, gas, WW1, WW2, illness, you name it. He had even killed himself a few times - the sixties were really not his best years. And for all those deaths, even one of his most recent ones, betrayed by the people he called his family, nothing had hurt this much.

He was alone, which was unusual, and hungry, which was much less so. He waited for two days for the gnawing pain in his stomach to fade before dying a slow painful death of starvation. As much as Jack hated him, he had to admit that the Master was clever. Leaving him to starve without any access to anything that could provide the relief and instant reset of death. He curled up on the cold, hard floor, and fell asleep.

Jack woke with a gasp. There was an excruciating pain in his stomach, and when he opened his eyes he could see a large spike stretching at least two metres in front of him. He lookef down,to see it sticking through his stomach, and swore. A familiar pre-recorded voice came from behind him.
"Jacky boy, if you get off that thing soon enough, I'll leave you alone for seven days" the recording shut off.
"Shit" he said again.

He first tried to pull himself upwards, but barely budged a few centimetres before he lost too much blood and felt his life slipping away from him, staining the white floor crimson. He tried that at least fifty more times throughout the day, before realizing that he wasn't going anywhere - each death he slipped back to the starting position.
It took two more slow, painful deaths to come up with a plan, and he started to push himself down to the base, barely resisting the urge to scream in agony. That took another day, and another handful of deaths, and then he still had to use all his strength to try to tip over the spike. He didn't have enough of it, despite the resets, he had become emicated and feeble. Plan b, he started shifting the spike over to the wall - many more deaths and another day. He pushed against the wall as hard as he could and the spike toppled, crushing him under it, and he died of the impact.
When he came round, it was still long arduous work to pull himself up, and he bit right through his lip trying to stifle the screams, filling his mouth with the coppery taste of blood. He gagged and choked on his own hot red blood, unable to swallow or spit, and instead passing out on the cold, hard floor, sliding off the end of the spike, and losing his grasp on life.

He awoke cradling his stomach, and true to his word, the master left him alone for a week - alone with no food or water. The master retured on the seventh day, when he was close to his third death of dehydration. Mouth and eyes dry, barely able to see, crying out for water as his body yearned for moisture. He shot him without the usual preamble, giving him instant blessed relief which didn't last for long.

When Jack came round, he was in a glass case, and for the first time in months he could see the doctor.
He was weak, haggard, showing his 900 years, but he still looked better than Jack felt.
Inside his little prison, he couldn't hear anything, but he could see that the doctor and Tish were discussing something. Probably him, judging by the glances they cast in his direction. His feet were cold, so he looked down.
Water was bubbling up from a grate, slowly, but surely. He heard a voice, replaying inside the box from the master's speech outside. One spine chilling sentence.
"You wanted water."

Of all the deaths Jack had ever experienced, drowning was probably one of the worst, but he remained calm as the water washed over his head and he died, as peacefully as possible given the circumstances.
When he came back, gasping for air, there was none. He was still underwater and this time he panicked, scrabbling at the walls and trying to keep his head about the water for as long as possible and letting out a hoarse scream when he went under. The third time, and the water was already at the top, there was no escape, but that didn't stop him from trying- kicking and hitting at the walls and ceiling, as he drowned again and again and again.
On the eleventh time, he gave up, and watched the Doctor's horrified expression as the life left his body.
He came round and he could breathe again, left soaking wet at the bottom of the cage. He doubled over, retching and shivering and shaking and crying,  until with a loud gunshot, the case shattered and he died.

Over the next eight months he experienced every type of torture imaginable. Electrocution;  dissection while conscious; branding; crucifixion;  hanging;  poison;  gas; a memory cube; being burned alive; even rape.
That was another of the worst, tied down and gagged with barbed wire. It was the destroyal of one of his favorite things, something safe, something good, something he loved.

Throughout all that, he remained unbroken. Damaged, yes, but still unbroken, until it happened.

Jack was sitting in his cell when it happened. The master came in and he tensed up, but he just put a projection on a screen and left.
That was when his heart broke.
It started off with basic CCTV footage of a street, and then he saw him. A familiar man in a well fitting suit. His face was scarred and his eyes were filled with sadness. A tochlophane flew out from a deserted building.
"Are you authorised to be here."
"Nah, but I'm looking for someone, so if you could piss off?"
"What is your name?"
"Jones, Ianto Jones, undesirable number two, and I'm looking for Captain Jack Harkness"
"Say Goodbye"
"Yeah, I will. Jack, I love you,  don't blame yourself....."
He broke off with a scream as he crumpled to the ground, dead, and Jack echoed his anguished yell.
Tears stung Jack's eyes, his throat ached from screaming, and he couldn't breathe from crying so hard. His heart felt like it had been shattered and someone was stamping on the pieces. Jack gave up hope, he was completely and utterly broken.

Captain Jack Harkness knew pain, but he didn't know it could be quite this bad

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