John Malone has structured TripAdvisor Inc. like he’s ready to make a deal. Malone, chairman of Liberty Interactive Corp. as well as several sister companies whose names start with Liberty, is known for engineering complex and lucrative financial arrangements. In August, he did a tax-free spinoff of Liberty Interactive’s controlling interest in TripAdvisor, a $9.7 billion website where users write reviews for vacation resorts. That transaction may soon lead to another.

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