Biggest possible Lithuania?

I don't clearly recall when, but I do recall that there was a point the Polish-Lithuanian Commonwealth's king was very close to also inheriting the throne of Russia - kill off a few people to make it happen, somehow make the whole thing stable, and have a Lithuanian noble start a dynasty.
 
Depends. If you want to keep it strictly as Lithuania, have it push deeper into Russia, say, by making the Golden Horde disintegrate early enough that the Lithuanians can take advantage. A Lithuania that has adopted Orthodoxy and is essentially a Ruthenian principality with a Baltic ruling dynasty unifying Russia instead of Muscovy...

If the Polish-Lithuanian Commonwealth counts, just don't have Sigismund III Vasa refuse the Boyars' request to have Wladyslaw IV in Moscow in 1610, eventually uniting Russia, Poland and Lithuania under the House of Vasa.
EDIT: The Boyars demanded that Wladislaw rule in Moscow and convert to Orthodoxy... while that might be a step too far, simply preventing Sigismund from demanding that they agree to himself as Regent (while demanding that they convert to Catholicism) might be enough to get the religious issue to a more... negotiable state, which might have the knock-on effect of stabilizing things in modern Ukraine if such a settlement is applied there too.
 
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One major question is how big can Lithuania get without the ruling classes getting Polonized or Russified. Inheriting the throne at Cracow did the former in OTL, taking Moscow would likely cause the latter.
 
One major question is how big can Lithuania get without the ruling classes getting Polonized or Russified. Inheriting the throne at Cracow did the former in OTL, taking Moscow would likely cause the latter.
This is a good point. There's simply not enough ethnic "Lithuanians" to maintain a distinct Lithuanian identity, even as the ruling class...
Maybe an earlier Christianization, standardization of and literacy in the Lithuanian language to make it the "prestige language", and foster a sort of "Lithuanization" amongst the conquered or otherwise united lands could accomplish this?
 
This is a good point. There's simply not enough ethnic "Lithuanians" to maintain a distinct Lithuanian identity, even as the ruling class...
Maybe an earlier Christianization, standardization of and literacy in the Lithuanian language to make it the "prestige language", and foster a sort of "Lithuanization" amongst the conquered or otherwise united lands could accomplish this?
What about the Lithuanians converting not to Christianity but to Islam via the Golden Horde? Could that work as well?
 
If by biggest Lithuania you mean ethnically Lithuanian state then best POD to achieve it is 13th century Teutonic Order screw (successful Herkus Monte perhaps?). That would allow Lithuania to absorb areas of Prussia and Latvia, inhabited by fellow Balts, who could be assimilated by Lithuanians.
 
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