Once colleagues and close friends who worked together to captures thieves and shared drinks on the roof after work, Nate Ford and Jim Sterling is a friendship gone sour after the death of Nate's son and the collapse of his old life. Since then Sterling became Chief Insurance Investigator for I.Y.S. When he and Nate meet again in the Two Horse Job he initially thinks that Nate wants his old job back, Nate goes along with this story but you can't fool Sterling for long. As he finds out more about Nate's new life he begins to pursue him and the team, at times even resorting to using his intimate knowledge of his former friend to capture him, such as knowing about a picture draw by Nate's dead son that Nate could never leave town without. It is also shown that Nate and Sterling have a shared Old-Fashioned/Lowball drinking glass, which they pass between each other (since their I.Y.S. days) to symbolize who has the upper hand.At the end of the Second David Job Sterling became President of I.Y.S. having been formerly promoted to Vice-President after the First David Job. In the Zanzibar Marketplace Sterling is forced for the first time to work with the team instead of against them. But it all turns out for the better for him as he is invited to join Interpol. At the end of the Maltese Falcon episode, when Agent Bob asked, of Nate, Who is this guy? that Sterling replied, honestly, I don't know. as Nate had become someone that Sterling no longer recognized.Later it is revealed that Sterling has a daughter who Nate never knew about. In the Queens Gambit Job he uses the team to help him rescue Olivia from her step-father who is raising her as a chess prodigy. Although to the team he pretends that he just needs them to steal a piece of nuclear technology, not admitting any personal connection.He is rumored to have spent three-to-five days in the trunk of a car to catch someone.Sterling is famous on the show for being the only person Nate and Co. cannot beat, every encounter they have with him ending some sort of draw. This relationship is symbolized in the opening chess game of the Queens Gambit between Sterling and Nate, in which at the end only the two kings remain.While no one on the team trusts Sterling, Eliot truly hates him. In the Zanzibar Marketplace the mere sound of Sterlings voice is enough to provoke Eliot into beating him up.