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This paper explores distributed smart grid attack strategies to destabilize power system components using variable structure system theory. Here, an opponent is able to remotely control multiple circuit breakers within a power system, say through data corruption or communication network attack, to destabilize target synchronous generators through application of state-dependent breaker switching. In contrast to attack via a single breaker, the multi-switch case provides additional degrees of freedom that can lead to stealthier and wide-scale cascading failures. We provide a dynamical systems context for formulating distributed multi-switch strategies and execute such attacks on the New England 10-generator 39-bus test system.