Board Thread:Timeline Discussions/@comment-35708317-20180909134222/@comment-2236231-20180909142506

From wikipedia;

Hitler and Franco met only once at Hendaye, France on 23 October 1940 to fix the details of an alliance. By this time, the advantages had become less clear for either side. Franco asked for too much from Hitler. In exchange for entering the war alongside the alliance of Germany and Italy, Franco, among many things, demanded heavy fortification of the Canary Islands as well as large quantities of grain, fuel, armed vehicles, military aircraft and other armaments. In response to Franco's nearly impossible demands, Hitler threatened Franco with a possible annexation of Spanish territory by Vichy France. At the end of the day, no agreement was reached. A few days later in Germany, Hitler would famously tell Mussolini, "I prefer to have three or four of my own teeth pulled out than to speak to that man again!" It is subject to historical debate whether Franco overplayed his hand by demanding too much from Hitler for Spanish entry into the war, or if he deliberately stymied the German dictator by setting the price for his alliance unrealistically high, knowing that Hitler would refuse his demands and thus save Spain from entering another devastating war.

Spain relied upon oil supplies from the United States, and the US had agreed to listen to British recommendations on this. As a result, the Spanish were told that supplies would be restricted, albeit with a ten-week reserve. Lacking a strong navy, any Spanish intervention would rely, inevitably, upon German ability to supply oil. Some of Germany's own activity relied upon captured French oil reserves, so additional needs from Spain were unhelpful. From the German point of view, Vichy's active reaction to British and Free French attacks (Destruction of the French Fleet at Mers-el-Kebir and Dakar) had been encouraging, so perhaps Spanish intervention was less vital. Also, in order to keep Vichy "on-side", the proposed territorial changes in Morocco became a potential embarrassment and were diluted. As a consequence of this, neither side would make sufficient compromises and after nine hours, the talks failed.

In December 1940, Hitler contacted Franco again via a letter sent by the German ambassador to Spain and returned to the issue of Gibraltar. Hitler attempted to force Franco's hand with a blunt request for the passage of several divisions of German troops through Spain to attack Gibraltar. Franco refused, citing the danger that the United Kingdom still presented to Spain and the Spanish colonies. In his return letter, Franco told Hitler that he wanted to wait until Britain "was on the point of collapse". In a second diplomatic letter, Hitler got tougher and offered grain and military supplies to Spain as an inducement. By this time, however, Italian troops were being routed by the British in Cyrenaica and Italian East Africa, and the Royal Navy had displayed its freedom of action in Italian waters and neutralised the Vichy French fleet at Mers-el-Kébir in French Algeria. The UK was clearly not finished. Franco responded "that the fact has left the circumstances of October far behind" and "the Protocol then agreed must now be considered outmoded".

According to Franco's own autobiography, he also met privately once with Italian leader Benito Mussolini in Bordighera, Italy on 12 February 1941 at Hitler's request. Hitler hoped that Mussolini could persuade Franco to enter the war. However, Mussolini was not interested in Franco's help due to the recent series of defeats his forces had suffered in North Africa and the Balkans.

Franco signed the Anti-Comintern Pact on 25 November 1941. In 1942, the planning of Operation Torch (American landings in North Africa) was considerably influenced by the apprehension that it might precipitate Spain to abandon neutrality and join the Axis, in which case the Straits of Gibraltar might be closed. In order to meet this contingency, it was decided by the Combined Chiefs of Staff to include a landing in Casablanca, in order to have an option of an overland route via Moroccan territory bypassing the Straits.

Despite being non-belligerent throughout the war, Franco's regime of open support to the Axis Powers led to a period of postwar isolation for Spain as trade with most countries ceased. U.S. President Franklin Roosevelt, who had assured Franco that Spain would not suffer consequences from the United Nations (a wartime term for those nations allied against Germany), died in April 1945. Roosevelt's successor, Harry S. Truman, as well as new Allied governments, were less friendly to Franco. A number of nations withdrew their ambassadors, and Spain was not admitted to the United Nations until 1955.

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From the above I gather that this might work;

Franco doesn't make all of those demands at once; rather with restraint enough terms are put forward to be acceptable to Hitler during thier only meeting in 1940 to establish an alliance. During the War and should it move in a course permitting demands not made then in the timeline will be made latter as requests of an ally.

There are other angles but I don't presently consider them as liley to have worked. But um that's from a lack of knowledge on my part regarding Spanish History.