Biggest possible Poland

Well, if you go the Poland-Lithuania route, and have them defeat the Russians before they get too powerful... well, Russia. Plus a considerable amount of eastern Europe. It would take time though. Sweden would prove to be a true enemy once Russia is taken care of, not to mention any surviving Khanates, if this is at the right time.

Oh, and sie Deutch
 
Well, if Poland goes Orthodox rather than Catholic, Poland can _become_ Russia. I'd say the biggest plausible that still has a _Polish_ identity would be the Commonwealth with perhaps some more of the Ukraine added (a Polish-Lithuanian-Cossack commonwealth?) including the Tatar bits and perhaps a personal union with Hungary (often dynastic links there OTL) plus east Prussia. Much larger to the east and we get too many Orthodox for stability, and doing an "end run" around the southern edge of the Slav-populated areas to get to Siberia ahead of the Russians seems a bit unlikely for various reasons.

Bruce
 
Throwing realism out the window and giving the Poles rather wankish luck...

One route is Poland-Lithuania-Hungary, which can potentially be achieved in the fifteenth century. Such a state could conceivably end up uniting all the non-Russian Slavs. Could it survive the rising star of the Ottomans?

Another route is Poland-Lithuania-Muscovy, which is of debatable stability. I honestly can't see any situation where a union of the PLC and Muscovy is maintained for any length of time--religious and cultural differences will combine with distances and foreign pressures (Sweden) to break it up. But if it should persist, then you basically have Russia, but with the capitol in Warsaw starting in the seventeenth century.

Then there's Poland-Lithuania-Sweden. Either Sweden stays Catholic or the PLC goes Lutheran. If such a union can persist to the nineteenth century, you can have it take part in colonialism in Africa.
 
For me a Poland-Hungary with Silesia and Galicia-Volhynia would be quite stable..but big...I think it could turn into a Eastern European "France".
 
Well, it would be a nice wank, but let's not go into ASB territory.

Problem with PLC is that eastern parts of the Commonwealth were to put it simply, empty - when compared to Western Europe. There is a reason why they were called "Wild Fields".

As for the Western border - people in the current Western Poland were almost always overwhelmingly German. Unless they are "Polonised" - which actually happened in many cases, but not in overwhelming numbers and not in areas where Germans were majority* - they will become a source of instability/discontent/irredentism/whatever come the age of Nationalism.

I have a hard time wrapping my head around idea that Poland takes the role of Russia through union with Muscovy. Such Commonwealth would be Poland in a name only - with nobility/ruling class adopting Polish language and mannerism (Golden Freedoms, sabres and moustache anyone?) with the rest of Russian/Rusyn/Ukrainian peasants speaking their own languages with their own culture and mostly Orthodox.

*Believe it or not, but many Poles have German-sounding names. At the uni I had Szmidt (Schmidt), Sznajder (Schneider) and Szwajgier (Schweiger). That is due to Medieval policy in Kingdom of Poland of importing German settlers to cultivate empty lands.
 
I think that Commonwealth that somehow avoids the worst crises of 17th. century and manages to reform itself, may end with all it had then + part of Pomerania, East Prussia, whole Livonia after successful another northern war against Sweden, and perhaps Crimea by sometime in 1700.
 
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