@ladytp replied to your post
But why does common thinking seem to assume – without any real reason besides blind hope – that Flint and Madi’s war would have succeeded in overthrowing British yoke, abolishing slavery and freeing those millions of future generations from the fate worse than death? Would a crew of pirates and runaway slaves really have defeated the British Empire, the most powerful in the world with unlimited resources at hand?
Because there were other successful rebellions against the British Crown in the same area in the same century. Because the American Revolution succeeded with scarcely more resources than the pirates and slaves could have mustered. The short answer is yes, and the long answer is even if they didn’t succeed, it’s important that someone would have tried, because it would have given others the notion that a rebellion could succeed in the future. The fact that the pirates of Nassau managed to annoy the British into offering the pardons in the first place is, as Flint rightly noted, a sign that England thought there was a possibility they could win, because you don’t pardon people you can successfully put down by other means that will scare other dissenters into backing down.
I mean, also, it was framed within the text as being viable enough to be a threat. Not only is there the economic disruption that a concerted fleet of pirates could enact upon trade in the Caribbean, but very specifically the threat was that with Maroon help, Flint could do what he was speculating and get 1 in 4 newly freed slaves to join their rebellion. The threat of that alone was enough to get the Spanish in Havana to join in; that’s the stick Rogers used to motivate them. None of the imperial powers in the Caribbean could withstand a slave rebellion, especially not one backed by a naval fleet disrupting trade.
And to back up what @flintsredhair says, the other part of the threat they posed was that they stood ready to expose the lie that the British empire was all powerful. Flint knows they’re not, because he was there when they lost Nassau the first time. Madi knows they’re not, because her island even exists in the first place and she’s free. The biggest enemy Flint and Madi faced (and the enemy that eventually defeated them) was fear of Britain’s inevitability. The assumption was that of course Britain would win eventually, so what was the point of fighting now. Institutional inertia is absolutely an enemy and every single time people in the show came close to showing that, they got shot down.
Also on a metanarrative level: there’s no tragedy to that ending if the war is a futile delusion. The stakes at the end have to mirror each other or there’s no narrative weight to what happens. On Flint and Madi’s side, you have darkness and loss now for the hope of freedom later. On Silver’s (and Max and Jack and Julius) side, you have the guarantee of freedom now and the equal guarantee of darkness and loss later. It’s ambiguous, sure, on if Flint and Madi would succeed. But I don’t think it’s ambiguous within the text they they could have succeeded.