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|Portrayed by||Harry Hamlin|
|First appearance||The Flood|
|Occupation||Cutler, Gleason, and Chaough partner|
|Residence||New York City, NY|
Jim Cutler is a partner at the (once) rival firm, Cutler, Gleason, and Chaough and a senior partner at the merged Sterling Cooper and Partners. He is the equivalent of Roger Sterling in his former firm CGC and Peggy describes him as "just like Roger (Sterling) but with bad breath." Cutler is often conversant and mild-mannered which belies his impatience and tendency for childlike escapades.
On one account, he brought his doctor to the newly merged SCDP-CGC office to give everyone a shot of "super vitamins" for their working over the weekend for Chevrolet. Instead making everyone productive, the booster shot only made Jim Cutler and Stan Rizzo hyperactive, and Don phasing in and out of consciousness. He has also brought Frank Gleason's daughter Wendy to the office on that working weekend and was later seen peeping on Stan and Wendy having sex.
He was part of the CGC team that was supposed to present to Chevrolet, and was vocally opposed to the merger of SCDP and CGC unless it gets them the account. In A Tale of Two Cities, it appears as if Cutler is still opposed to the merging of the firms, feeling resentment for having less control in the office, disrespected by Michael Ginsberg and annoyed by Bob Benson's constant meddling. He then assigns Bob Benson to Chevrolet as open defiance against Don and Roger. Ted having noticed this sat him down and said that he was dividing the firm into pieces, leading to a scene where Ted and Jim gathered the partners to propose a new name for the merged firms, Sterling Cooper and Partners, removing any partner name from CGC as a sign of goodwill and cooperation.
In season 7, episode 7, during a telephone conversation with Ted, Jim mentioned flying over Dresden in World War II, implying he was involved in the February, 1945, firebombing raids conducted by 722 heavy bombers of the British Royal Air Force (RAF) and 527 of the United States Army Air Forces (USAAF).