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Suppose I have Squee, Goblin Nabob on the battlefield. Does the legend rule apply if I then play Squee, The Immortal?

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No.

The following is the "legend rule":

704.5j If a player controls two or more legendary permanents with the same name, that player chooses one of them, and the rest are put into their owners’ graveyards. This is called the “legend rule.”

There's nothing concerning controlling two or more legendary permanents with similar names.

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