|“||He's like Nate... Evil Nate.||”|
The two competed, with Nate generally coming out on top, which left some bad blood between them. Sterling likes to believe he and Nate were friends, but Nate disagrees. Some time after Nate left IYS, Sterling became their principal insurance investigator. After the The First David Job he was promoted to vice president of the company.
Since then, Sterling has a knack for popping up in the middle of Nate's jobs, each time determined to get the better of Nate. After the events of The Zanzibar Marketplace Job, he was recruited by Interpol, giving him more opportunity to follow the team. Despite the animosity between them, Sterling has a grudging respect for Nate, leading him to maneuver Nate into helping him in The Queen's Gambit Job.
Sterling is also the target of Eliot's anger.
Olivia Sterling is Sterling's daughter. Like her father, she is an avid chess player and can hold her own against Nate in a chess tournament. She was raised by her step-father while she was working as an informant on his illegal activities.
Sterling tricked the Leverage team into going after her stepfather, allowing them to believe he was just another mark. Sterling was however planning on screwing them over when Nate caught up with him. Olivia begged Nate to let him go, saying that he was just trying to protect her.
Sterling is first introduced in The Two-Horse Job, when his investigation of the mark's claim crossed the team's con. He immediately sets his sights on foiling the con, and on bringing Nate down.
- The 12-Step Job (in Nate's hallucination)
- The First David Job
- The Second David Job
- The Zanzibar Marketplace Job
- The Three Strikes Job
- The Maltese Falcon Job
- The Queen's Gambit Job
- The Frame-Up Job
- The Long Goodbye Job
- Languages Spoken: Chinese (Mandarin, as seen in the Two Horse Job).
- Languages Spoken/Understood: Arabic (as seen in The Queen's Gambit Job).
- Lip-reading (as seen in The Queen's Gambit Job).
- Chess (as seen in The Queen's Gambit Job).
- He is one of the only characters in the series to have their own theme music.
- The DVD commentary for The Maltese Falcon Job notes that since their I.Y.S. days, Nate and Sterling have had the practice of passing an old-fashioned glass back and forth, to symbolize who has the upper hand. It first appears in The First David Job, when they meet on the roof of I.Y.S. Headquarters, and again in The Second David Job in Sterling's office. Later, we see it in The Zanzibar Marketplace Job when Sterling lets Nate know he's aware Nate has returned to drinking. When Sterling confronts Nate in his apartment, the glass returns to Nate's hands. The glass makes its final appearance in The Long Goodbye Job.
- According to the same commentary on The Maltese Falcon Job, Nate and Sterling were once best friends, and had a regular drinking appointment on the roof of I.Y.S. Insurance.
- Rumored to have spent three to five days in the trunk of a car to catch someone.
- Did hide in the trunk of a car in "The Zanzibar Marketplace Job".
- Until "The First David Job", he had never met Parker.
- He seems more jaded than Nate, as he cynically states in The Two Horse Job: "We're insurance men, Nate. We don't care who's innocent or who's guilty. Just who pays."