Dumbest strategic decision that each country participating in WWII could have made, but didn't?

Say, since everyone is saying that the worst thing Finland could do would be fully committing forces to Leningrad... Why? I don't get it. Would helping the Germans out with the siege really weaken them that much in other areas?

The attack would have been very costly to the Finnish military and the whole nation, which in the following years was in terms of supply dependent on Germany anyway. More death and loss of materiel than IOTL all around, in conditions where the Finnish supply situation was precarious as it was. And even if Finland would have managed to take Leningrad, it would have shared a direct responsibility of the civilians in the city, something the Finnish leadership wanted very much to avoid - history would have seen Helsinki as directly responsible when the Nazis would have killed millions one way or the other and Finland could not have done anything about it, even if it would have wanted to. We need to remember the scale of things here: the city of Leningrad had about as many living souls in it as the entire Finnish nation did.

Like wiking says, there was always the possibility that the USSR would rebound even with Leningrad lost, and if that happened, Stalin (or whoever was in charge then) would have aimed to murder Finland with extreme prejudice. The country would have definitely been joined to the USSR after the war, we likely would have seen hundreds of thousands more Finns dead due to the Soviet retribution, and today Finland, if it existed as a relevant entity, would have a large Russian minority if not an outright majority.

And then there is the "victory" option... With hindsight, we know that even if a Finnish assault on Leningrad would have led to the Nazis winning the war, the general outcome would have been worse than IOTL for everyone involved, Finland included. The positives of any irredentist wet dreams about a Greater Finland necessarily pale in comparison.

Quite simply, with hindsight, the best outcome of WWII for Finland was retaining independence and as much of the prewar territory as possible, while avoiding death and destruction, and that the Allies in the end win the war. The OTL is pretty close to the optimal realistic outcome of the war for the Finnish nation, the loss of the 1920 borders notwithstanding. In the entire war, Finland lost roughly 100 000 soldiers and 2000 civilians. Those civilian losses are mind-bogglingly low for a nation stuck between Stalin and Hitler. The closest comparison among combatant nations in WWII is, I believe, Australia. Also in terms of economic losses Finland still comes ahead in comparison to most other minor Nazi allies, even if we factor in the heavy war reparations to the USSR. For this thread in general, we can say that the outcome of WWII for Finland means that the Finnish leaders did not really do any major strategic blunders. Things could have easily been much, much worse.
 
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snip ... Op. Pike effects... snip

You're not taking into account the very real (and IMHO quite probable) possibility that, upon becoming PM and losing France, Churchill strikes a deal with Stalin before the latter had a chance to launch an invasion of Iran and/or Turkey.

Winston Churchill said:
If Hitler invaded Hell, I would make at least a favourable reference to the devil in the House of Commons.
 
Romania could have tried to retreat to the Carpathian line instead of switching to the Allies. It might have worked, but it would have caused great bloodshed throughout Romania, but spared a lot of what went down on Hungary instead (especially in Budapest)
 
For this thread in general, we can say that the outcome of WWII for Finland means that the Finnish leaders did not really do any major strategic blunders. Things could have easily been much, much worse.
Wouldn't for Finland though staying neutral be better? How much room was there for Helsinki to play this way?
 
Wouldn't for Finland though staying neutral be better? How much room was there for Helsinki to play this way?

The problem with neutrality was being alone while surrounded with aggressive totalitarian nations that are potential enemies, ones invading and annexing nations left and right. A Finland that did not ally with Germany would have been seen as potentially hostile by both sides and treated as such. It was also de facto blockaded by the Soviets and the Germans in 1940-41. In 1940, facing a renewed Soviet invasion alone was seen as a very real outcome of neutrality. The lesser fear was merely national-level starvation due to the poor harvest and the de facto blockade.

Finland was not Sweden, unfortunately. Its ability to stay neutral was much more limited. In 1940, only the Germans could give ironclad promises of direly needed weapons, food, fuels, etc. They could also deliver them directly through the Baltic. Under the circumstances, it was an offer that was very hard to refuse.
 
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Deleted member 1487

You're not taking into account the very real (and IMHO quite probable) possibility that, upon becoming PM and losing France, Churchill strikes a deal with Stalin before the latter had a chance to launch an invasion of Iran and/or Turkey.
I don't think you're remembering that Churchil and Stalin did not care for one another, plus they'd already be at war.
 
Anything involving Winston Churchill without the calming hand of General Alan Brooke. Brooke was offered overall command of the Mediteranean and Middle East in 1942 if he had left Britain there would have been no one to moderate Churchill which could have led to an invasion of the Baltic coast in rocket powered Panjandrums or an invasion of Germany via China.

Dill had been doing a fair job of working around Churchill. Which was one reason Churchill worked to get him replaced & kicked upstairs to the US. Brooke seems to have been more in sync with Churchill on strategy. That is fighting on the periphery & focusing on the Mediterranean.

Dill favoured a early return to NW Europe & was actively planning for it when replaced as CIGS.
 
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The UK and France commit airstrikes against the Soviet Union as well as support Finland in the Winter War. That would have made things...complicated.

The Great Mistake (by Onkel Willie) is based on this POD.
 
Germany : Invading Spain to take Gibraltar. Peninsular War 2.0 with both sides of Spaniards uniting with British support (again).

Vichy France : Joining the Axis as a full-blown member.
Well, this one MIGHT work not too badly if the Axis is massively lucky (ie. Britain bows out and Germany never fights the US).
 
Dill had been doing a fair job of working around Churchill. Which was one reason Churchill worked to get him replaced & kicked upstairs to the US. Brooke seems to have been more in sync with Churchill on strategy. That is fighting on the periphery & focusing on the Mediterranean.
Dill favoured a early return to NW Europe & was actively planning for it when replaced as CIGS.

Yet, Dill was a resounding success in the US, indeed some on this side of the pond thought 'he'd gone native'!
 
For Australia it would be the rumoured Brisbane Line, where the entire north of the continent would be abandoned in the event of a Japanese invasion.

In actual fact there was no such plan, although the CGS had been instructed to prioritise the defence of Sydney and Newcastle with Darwin as a secondary priority as the bulk of Australian forces were overseas.
 
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