Rothstein worked in food service on a passenger train while between semesters at university. The experience of being the lowest-ranked employee while interacting with a variety of people from different backgrounds influenced the development of Rothstein's character such that he screened job applicants and clerkship candidates for life experiences that taught them the value of hard work and character. Asked about it in an interview with Canada's CPAC public affairs station, Rothstein stated: "As lawyers, and as judges, we tend to live in a pretty enclosed world. Most people in the world are out there slogging out very, very difficult physical work - sometimes dangerous work. The experience that I had working in the dining car made me realize that there was a different life out there and that as a lawyer I was going to be lucky that I wasn't going to have to work outside, and in inclement weather, or perhaps in dangerous situations, or for that matter in the dining car. In those days we weren't allowed to sit down, if there was even one customer in the dining car, we had to stand all day with short breaks, and I want to make sure that my law clerks or the people I'm working with have some idea about what that life is about."Upon graduating from the University of Manitoba and passing his bar exams, Rothstein went to work for the firm of Thorvaldson, Eggerston, Saunders and Mauro. Rothstein specialized in transportation law and taught for several years at the University of Manitoba. In 1992, Brian Mulroney appointed him to the Federal Court Trial Division and in 1999 was elevated to the Federal Court of Appeal in Ottawa. In 2006, he was Stephen Harper's appointment to the Supreme Court and became the first justice to have his appointment publicly scrutinized when he appeared before a parliamentary committee.