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This article discusses Henry VII's reaction to Charles VIII's 1494 invasion of Italy and conquest of Naples, and it examines the complex negotiations leading up to Henry's July 1496 entry into the Holy League of Venice, which had been formed seventeen months earlier to force the French from Italy. The article challenges the standard view that Henry was not concerned about the French conquest of Naples because he thought Italy too distant from England, and it refutes the idea of some historians that Henry encouraged Charles to invade. It also questions the view that Henry joined the Holy League only as a means to strengthen his political ties with leading European powers better to secure his dynasty, and only after he was exempted from the League's military and financial obligations. This article shows that Henry had a perceptive understanding of Italian affairs, and that he wanted a unified League that could counterbalance French power and deter another French invasion of Italy. [ABSTRACT FROM AUTHOR]