A good example is Waterloo – Napoleon Bonaparte really could have won, and it was very close. He wouldn’t have needed completely different circumstances, just a few different decisions over the previous few days. There was no inevitability to his defeat. But if he had won, what then? Would he have been able to reach a settlement and place a Bonaparte dynasty on the throne of France for a century, or had Europe changed since his heyday, and would the allies have rallied, raised another army and crushed him a few months later? Probably the latter. This is the answer to a lot of counterfactuals – if the Ottoman Turks hadn’t captured Constantinople in 1453, they’d have captured it in 1454. But on the other hand, suppose Lenin had died in a bank robbery in the early 1900s. There would have been chaos and revolution, but Bolshevism would be an obscure sect, filed next to People’s Will, and Russia might have gone down a much less bloody path.

Source: Inevitability in technology — Benedict Evans