In my opinion, he did have a fee simple interest in the property for the short interval between the time he acquired the property as high bidder and subsequent assignee and the time he transferred it to the LLC.  It doesn't matter how long that period was because the deciding factor would be that he had some kind of interest - and that would be fee simple absolute - that he transferred to the LLC.  If not, then the transfer to the LLC would be null and void and very definitely a problem in the chain of title in either case. 

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