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The War of the League of Cambrai was fought from 1508-1516 by...basically everyone who had any interest in Italy at the time (which was most of Europe). It was a mess:

  • It's been described by one period expert as "the least comprehensible war I’ve ever studied."
  • Here on the stack, it's been mentioned that "most factions within the war were at one time allies and at others enemies."
  • The list of belligerents on the Wikipedia page has to do some amusing contortions to correctly represent what side each country was on at any given time.

You get the idea.

The aforementioned Wikipedia article does a respectable job of covering when various states switched sides in the war, but is a little light on why. What was it that caused this war, in particular, to be so messy and confusing?

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    Are you surprised that rulers were flip-flopping?
    – user69715
    Commented Oct 6, 2017 at 17:34
  • @user69715: But they did so much more than was usually the case. So it was kind of "surprising."
    – Tom Au
    Commented Oct 7, 2017 at 6:44

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There were three major players in Italy: 1) France 2) Spain/Holy Roman Empire (HRE) (treat them as one unit since one man, Charles V, ruled both, and 3) Venice, the "local bully."

The first stage of the war started when the other Italian states asked two large, outside powers, France and Spain/HRE to help them against Venice. That's why it was the League of Cambrai. In the second stage of the war, France was seen as the bully, and first the Papal states, then Spain/HRE allied with Venice against France. Henry VIII"s England also joined the anti-French alliance.

In the final stage, Venice decided that Spain/HRE was the greater bully, and defected to the side of France, its former enemy. This was the way things stood when the war ended in 1516.

Venice was vindicated over a decade later, Rome was sacked by HRE troops in 1527, which induced the Papal States, and even Henry VIII to side with France against Spain/HRE.

But all this illustrated a rule that every boy learns on the playground: "You don't want to be the odd man out in a three way fight." At times, each of the three main parties was the "odd man out," and each strove hard not to be. The description from Machiavelli as "the least comprehensible war I’ve ever studied," refers to domestic and political issues in which he specialized. But it may best be understood in the context of a schoolyard brawl.

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    This is kinda what I came up with it when I looked into it. Basically, the Pope and buddies started the whole war to stop someone (Venice) from conquering Italy. So if anyone else, as a result of the war, got to a point where they could conquer Italy, that entire crew would then be against them. Kind of like how England's foreign policy for centuries was "Don't let anyone conquer Europe", and that had them situationally allied with or against France.
    – T.E.D. ♦
    Commented Oct 9, 2017 at 21:34

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