It started because the President's wife was crazy. Or rather, the whole plot was enabled by the utterly bizarre direction the president's wife's paranoia had gone in. Obviously, any woman who was willing to marry that gluttonous pig of a man had to be at least a little crazy, but there's a certain amount of respect that one could give a woman who was willing to do that, after all, she was obviously, sincerely dedicated to her gold digging. And to some people, that was excusable. But no, this woman was crazy for other reasons, such as her utter obsession with the phrase 'what do we do if...'
So it really, it starts like this.
Cloud's rear end hit the ground in a graceless sprawl and he cursed mentally. He'd had more than enough practice with this kind of landing than he ever wanted, but he still never seemed to get any better at it. Dusting the dirt off his pants, vest and entire left arm, he checked that the surroundings were the same as usual. They were. He was exactly where he had been sixty eight years in the future, and the landscape was essentially identical even if the individual tufts of shrubbery around him were not.
The time loop thing that he had somehow found himself trapped in had been pretty cool the first time he'd gone back in time. And the second as well. Now though…the novelty had worn off.
The first time he looped, he had done everything right. He killed Sephiroth, Hojo, and the Shinra executives save for Reeve, stopped Nibelheim's burning, and made a massive thermite reaction with Jenova in the middle (on his third life, he added rocket fuel and dynamite just for kicks). The reactors were all safely decommissioned and dismantled after he, Tseng and Reeve took over the crumbling corporation. They built a truly massive array of wind turbines and solar panels in their place. He had made sure Zack and Aerith met and got married, and he himself married Tifa- once- (and made sure not to encourage anything whatsoever in the next time, or any time after that). In his third life, he lived long enough to see Nanaki's environmental initiative buy out the pitiful remains of Shinra's science and weapons departments from them specifically to turn its buildings into greenhouses.
When he fell into his fourth life, he started getting suspicious. Aerith was not amused by his subsequent harassment and eventually filed a restraining order with Tseng. Not that that stopped him from breaking into the church to visit her whenever he felt like it.
By the time he died for the fourth time and tripped headlong into his fifth life, he was pretty sure there was nothing better that he could possibly do for the world. After a quick, expletive filled, one sided shouting match at the ground, he decided to do everything he didn't think was supposed to happen. He saved Sephiroth, told him about Hojo's lies and cackled in the background as the Silver General decapitated the scientist in the middle of the cafeteria. He even made an effort to be slightly disappointed that the crazy scientist had died. He had tried to convince Sephiroth to spare him just to be contrary.
He conspired with both the newly nicknamed 'Sephie,' Reno, and Vincent to drive President Shinra insane by 'haunting' the man and his family with 'Hojo's ghost.' He created a new fashion of legwarmers and fluffy slippers with Aerith's help, and got Tifa's help in braiding all of Nanaki's fur. All of it. He cremated Jenova and got Cid to build a ship to launch the ashes into the sun. No matter how contrary he wanted to be, that alien was still on his kill list. And just to piss of the ancients (or the lifestream or Gaia or whoever was the one responsible for this time loop mess), he made it a point to be the worst human being he was capable of being. He was as disreputable as possible, drank himself to almost-death despite the mako, twice, deliberately tried to dig up the WEAPONs for sparring practice, and gambled on every single chocobo race he could, mostly to the effect of winning huge piles of money that he didn't actually spend. He argued with everyone about everything, sulked, lied, brooded, played very well at having a bipolar disorder, and generally succeeded at ticking off or confusing the hell out of everyone he met. On his 'thirty-eighth' birthday which was actual his two-hundred and eighty-ninth, he off-ed himself just because he was pretty sure he was supposed to live, and there really wasn't a point to that anymore. All in all, it was a rather therapeutic life.
The only thing that changed when he started over in his sixth life was that he landed rather painfully on his head.
So in the beginning of his sixth life, Cloud threw a minor hissy fit that destroyed the top of Mt Nibel before he skipped off, avoiding Midgar and Jenova entirely. He ended up in Cosmo Canyon where he started producing Nanaki and Cid's wind turbine designs. When Shinra came calling, he told them as politely as possible, with a giant sword in hand, to back off or there would be consequences.
Consequences were had.
Eventually his company bought out Shinra.
After he captured Sephiroth, browbeat the remainder of SOLDIER corps into working for him and subsequently took over the world, he took some time off to visit a pitifully small island off the coast of Wutai. He figured that if the Planet was still looping him for doing something wrong, the Planet could well take care of the problem itself. He gleefully threw both Jenova and a drugged-into-a-literal-coma Sephiroth into the bubbling, molten soup. Reno, who accompanied him, had cocked his head to the side and said "you know, people tell stories about flinging fair-haired maidens into volcanoes to appease the gods." He then spent two entire weeks giggling about the 'virgin sacrifice' of Sephiroth. Given that he had thrown a sentient being - who he had, in a past life, been on relatively good terms with - into a volcano, Cloud wasn't sure if he should have been more concerned about his lack of compassion or not.
In his seventh life, Cloud threw his hands in the air and became a beach bum in Costa del Sol. That lasted only three years until he tripped into the past while trying to get a margarita.
In his eighth life, he upgraded from a beach-bum, to a beach-bum-anti-Shinra-cult-leader. He managed to convert just under five million people to the theory of 'If you ignore anything hard enough, it will eventually go away.' He liberally applied that theory to everything Shinra did, sold, said and wanted. Eventually, he was dragged into a council to help draft a constitution for the new country that Costa del Sol was forming. They didn't even bother sending an announcement to Midgar before they simply demolished the Corel reactor. He got pulled out of that life only a few decades later, but counted it as a win solely because it had taken only a year until he had acquired a decent tan. (This was opposed to the two and a half years it had taken in his sixth life. It turned out that Mako healing made it all too easy to fluctuate between 'burned redder than a lobster' and 'about as pasty white as Vincent' with absolutely no in-between.) On the down side, Sephiroth went insane anyway and burned down Costa del Sol when an entire beach full of people refused to hail Jenova as their queen.
Cloud's ninth life started as an attempt at doing things right again. It had been a few centuries since he'd done anything like it, so he figured that he had taken a long enough break. It was almost immediately interrupted by Reno recruiting him to the Turks after he caught Cloud breaking into Shinra's giant storeroom of the science department's filed-in-triplicate paperwork.
Fascinated, he accepted the recruitment and spent the better part of a decade as Reno's not-sidekick, not-partner-in-crime, definitely-not-covering-for-him-Tseng-I'm-innocent-really partner. He ended up pushing a lot of paperwork and running for a lot of what passed for coffee, but it was more fun than he'd ever had while working for Shinra. And if he learned the dirty little secrets of everyone in Shinra, as well as the millions of loopholes that he could exploit, well, it was a well earned perk of the job.
He took particular joy in making sure that every attempt Hojo made at getting Sephiroth to go to Nibleheim was somehow diverted by 'incomplete paperwork' or if that didn't pan out, simply making the paperwork, emails, phs messages, and memos mysteriously vanish. He took perverse pleasure in writing up the paperwork to admit the dear Professor to Shinra's Psych Ward after the man broke down. The best part about that was that it was entirely legitimate- the man had cracked and screamed his demands, along with bits and pieces of 'intellectual private property of Shinra Electric Company' regarding Jenova and Reunion, in an incomprehensible jumble of rage. In the middle of the loading bay. In front of two entire platoons of infantrymen, seven third-class soldiers, four second-class soldiers and Director Lazard, who 'just happened' to be visiting at the time.
And then, as icing on the cake, Sephiroth, Reeve and Tseng collectively overrode President Shinra's whining and had Jenova desiccated, salted and burned.
After that it took relatively little prompting- read: Sephiroth's glare- to get the president to look into the validity and logic of every other project Hojo had ever touched.
Within five years, Midgar was down to two functional reactors while actual research was conducted on the nature of Mako and its effect on various forms of life, both short-term and long-term, and in varying concentrations. Not that it would matter if it was harmless. The president was quite fond of wind turbines, as they required infinitely less maintenance than the volatile reactors did, and therefore cost less money.
By the time the Cloud started to feel the itching-burning 'about to be flung backwards through the time-stream' sensation again, he was ninety seven years old, still looked eighteen, and was cackling madly much to Vincent's chagrin. This time, he was going back with a plan.
And so, it begins like this.