Speculation: Greatest City or Nation that Never Was

I would say Lucca. Important Roman city in a well placed position, was the capital of Tuscia in Lombard age, had an important Christian relic (Volto Santo), was one of the first cities of the West to cultivate silk and create silk clothes of high quality, and able bankers, not counting the presence of characters (Castruccio Castracani, Paolo Guinigi) which if more successfull would have projected the city to become dominant in Tuscany. It was the only city which resisted to Florence after all. Just think how obscenely rich could have become if retaining permanently Carrara and its marble caves. Or if Luni rather than declining would have been absorbed by the same Lucca, becoming its harbour. And lastly if ruling definitely over the small but really fertile Garfagnana. And was a city able to reinvent and prosper in different ages - the rule of Elisa Buonaparte even if brief rejuvenated the city.
 
Paraguay. Before the disastrous war against Brazil and Argentina (1864-1870), it was the richest and most technologically advanced country in South America. In the war, it lost a quarter of its territory and up to 70% of its population and never recovered.
 
I would say Lucca. Important Roman city in a well placed position, was the capital of Tuscia in Lombard age, had an important Christian relic (Volto Santo), was one of the first cities of the West to cultivate silk and create silk clothes of high quality, and able bankers, not counting the presence of characters (Castruccio Castracani, Paolo Guinigi) which if more successfull would have projected the city to become dominant in Tuscany. It was the only city which resisted to Florence after all. Just think how obscenely rich could have become if retaining permanently Carrara and its marble caves. Or if Luni rather than declining would have been absorbed by the same Lucca, becoming its harbour. And lastly if ruling definitely over the small but really fertile Garfagnana. And was a city able to reinvent and prosper in different ages - the rule of Elisa Buonaparte even if brief rejuvenated the city.
Ppssible POD: in the aftermath of the Battle of Montaperti Firenze is indeed destroyed like some had proposed, then Lucca, bolstered by Florentine guelph exiles, takes up its role as the leading guelph city and later on as the most important Tuscan city.
Along the same lines I would love to see a Pisa wank, with a reverse Battle of Meloria leading to Genoa being crushed and Pisa establishing a Thyrrenian empire over Corsica and Sardinia.

Edit: just saw that the thread is quite old, sorry for posting on it.
 
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Paraguay. Before the disastrous war against Brazil and Argentina (1864-1870), it was the richest and most technologically advanced country in South America. In the war, it lost a quarter of its territory and up to 70% of its population and never recovered.
Not really... Paraguay definitely had some merits (a huge literacy rate for a Latin American country), but to say it was rich and advanced is a hyperbole, Paraguay was an agrarian society and its landlocked position stalled many prospects of development (hence the whole Platine clusterfuck) and with a strict isolationist economical policy left Paraguay as a pretty backward place.

Not judging no one here, but most of this Point of View here (Brazil) comes from revisionists that came with a ridiculous narrative of the Triple Alliance as agents of the British Empire to destroy the brave defiant Paraguayan power (Paraguay started the war, but it's our fault for some reason), even though Brazil has cut relations with the UK at the time.
 
Any Balkanic state - Bulgaria, Serbia, Bosnia, Croatia - had the chance to become quite great. Heck, if they had managed to push back the Ottomans, we'd know the Balkan Peninsula as the Haemic/Hemic Peninsula today.
 
In my opinion, the Inca could have been great had they managed to resist the initial Spanish conquest (which is not unthinkable). Our POD is that the Spanish arrive before 1493 and Huayna Capac's conquests of the Altiplano and Atacama (which led to the Inca being massively overstretched, leading to decentralized military command for the north which IMO was one of the primary causes of their civil war down the road).

So basically the Spanish discover the Americas sooner and encounter the Inca in their prime, fresh off their victory of wiping out their only meaningful rivals but also before they do anything stupid. Because it's impossible to predict what would happen in any meaningful sense, let's assume the Spanish do manage to conquer the bay of Guayaquil but are unable to conquer Cajamarca in a ground invasion - in this scenario, the Inca make better use of their tactic of pummeling the Spanish in mountain valleys from geographical vantage points and are able to cause a stalemate to the point where the Spanish do not disrespect the Incan attempts to initiate trade.

At some point the Inca have to establish themselves as equals in the minds of the Spanish, so let's go out on a limb and say that there are farsighted Incan leaders who manage to secure trade deals for European weapons and naval vessels. The weapons are important for obvious reasons, to not be reliant on Spanish good will to survive. But the ships are even more crucial. It allows them to contact other nations, at the bare minimum the Portuguese and ideally either France or Britain - hopefully one of the three would be willing to trade with the Inca and/or offer security guarantees against Spain. Regardless, the Inca will need to be penned in on all sides by the Spanish (and the Amazon, where they were notoriously bad at fighting and entirely uninterested in) in order to establish a non-expansionist culture.

The ships are also important because the Inca do actually have prior knowledge of a land across the Pacific due to their contact with the Polynesians. It's entirely possible that they can pioneer a Pacific route to Indonesia if there are leaders who understand the value in doing so, and their objective after that would be to develop a stayover port, where they could host cargo ships from Asia as well as export some of their vast reserves of precious metals and gems in the Andes.

If you end up with a mercantilist Inca Empire in control of its own resources, they can cruise into the modern age in relative luxury, and there are many directions they could go from there.

The Inca could become a sort of second home for Protestantism, since they want to stick it to the Spanish and are powerful enough so that if Austria, France, or Poland decides that they've had enough of this Luther guy, the Protestant movement could survive there,
 
Zanzibar: A perfectly placed city for a trade hegemony, yet it truly was dealt an awful hand through history. Give it more time and trade influence across to Indian bringing in migrants, it could then be a very large city by the modern area straddling the islands and onto the coastline.

Palmyra: In a no Islam scenario or one where the Umayyads choose it as their capital instead of Dimshaq, becomes the capital and most populous city in Syria, especially with canals and a continued economic boom in Baghdad or Cteshipon.

Baghdad: With certain criteria, going back to the Abbasid period, could be the largest city in the Arab world instead of Qahirah. Ways for this to occur, briefly:

-No moving of the capital to Samarra in the late Abbasid era.

-No Zanj, Khawarij, etc.... rebellions to destroy its vital countryside. This would entail the slowing of the slave trade to the Batihah Sawad, which contributed to the mass poverty leading to Baghdad's economic failure in the 1000s AD.

-No Mihna, or inquisition. This was the fire that started the end of the Abbasid period and of the caliphate.

-Keep the Abbasid court religiously neutral but publically Sunni. Simply put, keep the vicious and greedy Mu'Tazila from the reigns of power in Baghdad, which caused the fall of the Abbasid caliphate (the Abbasid was essentially a Mu'Tazilite state as opposed to a Sunni one).

All these points butterfly the Mongol siege, as we assume the Caliph is not idiotic enough to assist the Mongols in taking Alamut from the Hashashin and putting forward no resistance at the walls of Baghdad or more importantly in the south in the defense of Basra.

Vijaynagara: A state with huge potential and with a city likewise. It could've become a trade juggernaut, but was snuffed in the cradle by the Bahamani, who also could fit this criteria from its fort at Bidar.

New Orleans: Speaks for itself, once the largest and most diverse city in the southern US.

Novgorod: The typical.

Etc... I could go all day.
 
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France if it remains west/Atlantic facing and avoids sluggush demographic growth could become a huge force to be reckoned with and the "China of Europe".
Even today I would argue that the country is far from having attainted its full potential. Marseille could become Europe's southern gateway, geography is on its side but policies aren't.

Some for the British Isles too:
-Catholic Emancipation enacted at the same time as the Act of Union. In effect a "fully united" kingdom. Ireland could end up with 20M+ inhabitants by the 21st century. Britain will be different, a more equal and more united nation with a clear Anglo-Celtic identity. Dublin may have 5M inhabitants and be a clear rival to London.
-No relative economic decline post WW2. Glasgow, Teesside and parts of the North avoid deindustrialisation. Combine this with a likely even more prosperous City and the UK may be up to 30% richer than today per capita.
-Bristol: The City went into relative decline from the 19th century onwards. There's no reason why it couldnt have rivalled Liverpool.
-London Southbank: Only just starting to come out of its torpor.
 
London for me is the "could have been the greatest city in the world" with respect to what could have been, but to most people who do not know this London is the greatest along with New York anyway.

For me, it is down to three historical reasons and one current reason:

Firstly: In 1698 the Old Palace of White hall was destroyed due to fire. Plans to rebuild it never came to materialization.

Secondly: In 1666 most of the old fortress of londinium was destroyed in the great fire and there were plans to rebuild it but that also never came to materialization.

Thirdly: Over the centuries many buildings have been sadly destroyed.

Regards
 
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With a bit of bias, Vilnius/Wilno/Vilna.

Even after losing up to half of it's population in the plagues of the 18th century and just as much during the Deluge, Vilnius was still one of the biggest cities of Poland-Lithuania and later in the western regions of the Russian Empire in the 19th century. It was also a major center of culture and trade and, during the first decades of Tsarist times, housed an Imperial university. It was also built on a strategic location, quite literally between Poland/Germany and the Russian heartland (heck, one of the first railways in the Russian Empire was laid through the city), excellent for commerce, trade and culture.

Sadly, it was extremely neglected after the 1830 and 1863 uprisings and then had 80% of it's population either sent to concentration camps or repatriated to Poland during World War II... I know Lithuania is generally a super unlucky nation when it comes to history (only more unlucky in it's AH.com treatment), but with slightly better odds, Vilnius could have easily been a >million sized multinational cultural capital of Northeast Europe.
 
Ajuran sultanate, with its capital in Mogadishu which numbered between 50-100 thousand depending on the source which was one of the great trading centres in the Indian Ocean , the sultanate was a rich trading nation that had trading partners from the Swahili States to India and China and many states inbetween them, was very rich and strong, with the ability to hold of the Portuguese from conquering Mogadishu in 2 long drawn out wars, if it wasn't for the Portuguese monopolising trade within the Indian Ocean, this would have led to the Somalians urbanising more, since it was due to the Portuguese pushing them out of the ocean that lead to the southern Somali clans to turn to a nomadic life style due to the loss of trading income.
 
My country, Brazil.
We had and still have all the perfect resources for a huge empire. Minerals, lots of farmland, huge territory, a river system tempting of modernization and devleopment when it comes to transport, lots of able-bodied men and women if we have to fight, sea access easily leading to Europe and North America in the north and Africa in the east, a large (yet only recently-discovered) oil shale, and more.
It's depressing that the only thing that has held us for so long is a corrupt, tax-evading elite coupled with an uneducated, politically careless people.
 
My country, Brazil.
We had and still have all the perfect resources for a huge empire. Minerals, lots of farmland, huge territory, a river system tempting of modernization and devleopment when it comes to transport, lots of able-bodied men and women if we have to fight, sea access easily leading to Europe and North America in the north and Africa in the east, a large (yet only recently-discovered) oil shale, and more.
It's depressing that the only thing that has held us for so long is a corrupt, tax-evading elite coupled with an uneducated, politically careless people.
We have "lol no coal" though, so industrialization would be very hard, coupled with the whole scars of colonization it would a tough call to be a great power, even with all the stuff we have underground.
 
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