Discontinuous dynamical systems and multiagent systems are encountered in numerous engineering applications. This dissertation develops stability and dissipativity of nonlinear dynamical systems with discontinuous right-hand sides, optimality of discontinuous feed-back controllers for Filippov dynamical systems, almost consensus protocols for multiagent systems with innaccurate sensor measurements, and adaptive estimation algorithms using multiagent network identifiers. In particular, we present stability results for discontinuous dynamical systems using nonsmooth Lyapunov theory. Then, we develop a constructive feedback control law for discontinuous dynamical systems based on the existence of a nonsmooth control Lyapunov function de fined in the sense of generalized Clarke gradients and set-valued Lie derivatives. Furthermore, we develop dissipativity notions and extended Kalman-Yakubovich-Popov conditions and apply these results to develop feedback interconnection stability results for discontinuous systems. In addition, we derive guaranteed gain, sector, and disk margins for nonlinear optimal and inverse optimal discontinuous feedback regulators that minimize a nonlinear-nonquadratic performance functional for Filippov dynamical systems. Then, we provide connections between dissipativity and optimality of nonlinear discontinuous controllers for Filippov dynamical systems. Furthermore, we address the consensus problem for a group of agent robots with uncertain interagent measurement data, and show that the agents reach an almost consensus state and converge to a set centered at the centroid of agents initial locations. Finally, we develop an adaptive estimation framework predicated on multiagent network identifiers with undirected and directed graph topologies that identifies the system state and plant parameters online.