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Whoever said ‘the first cut is the deepest’ clearly had never had their life ended by a mystical being from the Dark Dimension.
As far as cuts went, number 23 had been a real whopper. It would have gone right through him if he hadn’t fallen between two rocks which stopped the incoming blade shortly before complete separation.
If he had still been counting, the one that had split his body into two neat halves would have been a hot contender for the top spot, purely for aesthetic reasons.
Around count 27, when a pile of meteors cracked his skull, Stephen was wondering how long it would take Dormammu to develop an understanding of time. Or when he would eventually grasp what Stephen was trying to do here. How hard could it be to understand what he meant when he said “I come to bargain”?
At a hazy 63, the one where his body was vaporised into subatomic particles, he began to wish it wouldn’t take the rather comical representation of an over-inflated ego 100 additional attempts to realise how ridiculous it was to try the same thing over and over again, expecting a different outcome. Stephen gave him kudos for creativity for that one, though.
He had been hopeful at first, when Dormammu had quickly caught on to the concept of déjà vu, recognising it as something new. He had severely underestimated, though, how little those beings in power are into any kind of change. They are more from the status quo fan club. Not prone to challenging their perceptions, adapting, and learning anything new.
They also had no concept of failure. Which, by number 229, when a myriad of daggers punctuated his body, was becoming ever so slightly annoying.
It wasn’t a secret, nor did it bother Stephen terribly, that people tended to think of him as irritating. Now this very treat was going to save the world. In a quiet moment much later he might even appreciate the irony of it.
His plan was based on the firm believe that he could out-stubborn anyone. How well that would work on a being of seemingly infinite power and resources, well, there hadn’t been much time to concentrate on the finer details, had there.
If it worked out, all of this would be a mere blink in the eye of the Earth’s population. He himself wouldn’t be that lucky. From his limited experience regarding time loops he knew he would remember all of it. As the one wielding the Eye of Agamotto Stephen held all of time in his hands. Except his own.
Regarding the expected pain he had taken a calculated risk. Since Dormammu had no concept of time Stephen had hoped he wouldn’t derive any pleasure from prolonged torture, but rather choose means of getting rid of him like you would handle an annoying insect. His body then would go into shock quickly, and they would jump back to him landing in front of the furiously hovering head.
Although, in all honestly, the repetition could be seen as torturous. And people would be surprised how long a second can actually be before the body and mind shuts off while you are blown to smithereens.
Shamballa - my ass. Way before the 600s his new mantra had become ‘Stephen, you moron’. Getting chopped into parts by a giant egg slicer ten times in a row can really put a dent in your day.
After the umpteenth time of burning him to a crisp Stephen started to suspect Dormammu was trying to bore him into admitting defeat.
“What do you want?”
Stephen cocked his eyebrow. “You are kidding me. We have been over this a thousand times. Literally.”
And with all his remaining valour he repeated: “Dormammu, I’ve come to bargain.”
The Ancient One had been right when she picked up on his motivation. It had been his fear of failure which had made him thrive to become the best doctor, but had also held him back from taking risks. But you only learn if you allow yourselves to make mistakes.
In the end Stephen beat Dormammu because he had an understanding the other one lacked: you can win by losing again, and again, and again.