US Air Date: 08/10/2007

Writer: Matt Miller

Director: Jason Ensler

A precious painting of water lilies changes hands several times, but in each transaction someone is murdered. Sarah, Casey and Chuck review photos of the dead art dealers to see if Chuck knows anything. Chuck flashes – someone named La Ciudad will be after the painting at an art auction tomorrow night.

Casey rents Chuck a tux for the auction, telling him he'll be fine as long as he knows how to tango. Sarah helps Chuck craft his cover identity: Charles Carmichael is a semi-retired software millionaire. This was how Chuck saw his future during his sophomore year in college, right before Bryce found stolen tests under his bed and alerted the administration. Casey tends bar undercover. Chuck gets drunk and is recognised by a friend from college, Allan Watterman, who actually is a semi-retired software millionaire. He makes Chuck feel bad about his life, until Chuck flashes on Allan's offshore accounts filled with insider trading spoils.

Chuck inspects the water lily painting, flashing on the frame. He's accosted by the beautiful and exotic Malena, who offers him champagne and challenges him to tango. Chuck goes for it, though he asks Malena to dance lead because he's only learned the female part. Casey spots who he thinks is La Ciudad; he and Sarah fight the man but it turns out he's really an MI6 agent who's also after La Ciudad. Seeing a scar on Malena's neck while they dance, Chuck realises that she's the real La Ciudad. Malena escapes and later tracks Chuck to Buy More, where she and Sarah have a rooftop fight with knives and brass knuckles. Sarah wins.