Sydney Prince

Sydney Prince is the main villainess from Chuck episode 3.04, "Chuck Versus Operation Awesome."

She was played by Angie Harmon, who appeared as the villainous Eve Goode in Glass House:  The Good Mother.

Sydney Prince is an evil operative from The Ring, who also headed a cell in Los Angeles. In the episode, the evil Sydney attempted to recruit Chuck's brother-in-law, Devon, after mistaking him as a spy. Through an earpiece she planted on Devon, Sydney ordered him to infiltrate an office building and kill a man inside the building, with the threat of blowing him up with the earpiece if he doesn't comply. The man was revealed as CIA agent Daniel Shaw, and knowing Sydney's plans, he shot himself and swallowed a capsule of amiodarone.

After Sydney enters pleased that Devon commited the deed, she removed his earpiece and gave him a Ring communications device. After she leaves, Devon (who thinks Chuck shot Shaw) revives Shaw with an adrenalin shot. Later in the episode, Sydney and her henchmen encountered Chuck at the Buy More store, which led to Sarah engaging in a fight with the villainess. Sydney later escapes, only for Chuck to hold her at gunpoint and force her to surrender. An unimpressed Sydney pulls out her phone as a decoy for a knife she had hidden behind her back, intending to kill Chuck. At that moment, Sydney is shot in the back by Shaw. As revealed in a later episode, Sydney is alive and in federal custody.