What if Bulgaria won the second Balkan war?

How could they have won? They had a good chance of winning before Romania and the Ottomans gang-banged them. The Bulgarians had refused to give silistria to Romania after the end of the First Balkan war, if they'd given this up then the Romanians probably would've stayed neutral or maybe even offered some support in exchange for it. The Ottomans might be dissuaded from joining against them if they collapse either the Greeks or Serbians and could even join on the Bulgarian's side to get some of Greece's Aegean islands.

How would this affect WW1? If the Ottomans still go Central powers then would Bulgaria go entente? The main reason they joined the central powers was for the territory they lost to the Balkan league which they wouldn't have lost if they won, they'd be much more willing to join the entente if they were offered Ottoman land which in turn would make Greece and Serbia go central powers, the Romanians would be 50/50 for either as both sides would hold land they want, although they would likely lean more towards the central powers if the Bulgarian lines collapse early in the war in order to get silistria and other land Bulgaria took from them.
 
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The best way to win the Second Balkan War is not to fight it. Romania and the Ottoman Empire joining the war is inevitable. Contrary to your assertion, Romania had been given Silistra, but it was not enough for them. Nothing would be enough, since the whole point of Romania's intervention was to keep Romania as the top power on the Balkans and this required Bulgaria to not defeat Greece and Serbia. The Ottomans meanwhile would never miss an opportunity to regain most of eastern Thrace along with their old capital Edirne
 
How could they have won? They had a good chance of winning before Romania and the Ottomans gang-banged them. The Bulgarians had refused to give silistria to Romania after the end of the First Balkan war, if they'd given this up then the Romanians probably would've stayed neutral or maybe even offered some support in exchange for it. The Ottomans might be dissuaded from joining against them if they collapse either the Greeks or Serbians and could even join on the Bulgarian's side to get some of Greece's Aegean islands.

How would this affect WW1? If the Ottomans still go Central powers then would Bulgaria go entente? The main reason they joined the central powers was for the territory they lost to the Balkan league which they wouldn't have lost if they won, they'd be much more willing to join the entente if they were offered Ottoman land which in turn would make Greece and Serbia go central powers, the Romanians would be 50/50 for either as both sides would hold land they want, although they would likely lean more towards the central powers if the Bulgarian lines collapse early in the war in order to get silistria and other land Bulgaria took from them.

Bulgaria can not really win against an alliance warfare in their position or they have to turn pro-Russia immediately and offer whatever suits them, who in return pressure Romania to enter the war. The risk is an earlier WWI with Romania joining the Central Powers.

And Ottomans joining Central Powers is not going to make Bulgaria join the Entente. This leaves the South East open to Ottoman attacks. Bulgaria really manoeuvred diplomatically to avoid such risky conflicts. Hence why Bulgaria joined the Central Powers as well and only after the Ottomans joined.
 
And Ottomans joining Central Powers is not going to make Bulgaria join the Entente. This leaves the South East open to Ottoman attacks. Bulgaria really manoeuvred diplomatically to avoid such risky conflicts. Hence why Bulgaria joined the Central Powers as well and only after the Ottomans joined.
With what troops? Bulgaria entering on the side on the Entente would have been catastrophic for the Ottoman Empire, especially during the Gallipoli operation. This is why they they were circles in Bulgaria which pushed for this course and why the Ottomans had to surrender territory to Bulgaria to get them to join.

Of course this in OTL. If there was no Second Balkan War, the situation would be even more desperate for the Ottomans.
 
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