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So far, every Straw Hat has encountered a Shichibukai:

First being Mihawk - Baratie Arc

Second being Crocodile - Arabasta Arc

Third being Gecko Moria - Thriller Bark

Fourth Kuma - Thriller Bark

Fifth Boa Hancock - Amazon Lily

Sixth Blackbeard - Pre-Skypiea/Impel Down

Seventh Jinbei - Impel Down/Whitebeard War

but they have not encountered the last Shichibukai, Doflamingo Doquixote. How do you think their meeting will play out, considering his and their history with his Human Auctioning House? Will he be another Crocodile, where he will beat Luffy several times before succumbing? Or will oda smack us in the crotch and reveal him to be a potential ally? (I won't like this if this is Oda's choice. I find Doflamingo to be a huge ass)