In 1968 he joined the Boston Globe. During his career with the newspaper, he served as its Washington correspondent and reported on ten Presidential campaigns. The Boys on the Bus, Timothy Crouse's account of the 1972 United States presidential campaign, included Oliphant as one of the prominent journalists among "the boys" covering the campaign.
In March 2005, Oliphant suffered a brain aneurysm. His account of the experience and his recovery appeared in The Globe on June 5, 2005,[3] At the end of 2005, he was one of 32 Globe staff members who accepted a retirement buyout package from the New York Times Company, owner of The Globe.[4]
In April 2007, Oliphant became involved in controversy arising from some vulgar remarks that talk radio host Don Imus made regarding African American players on the Rutgers Universitywomen's basketball team. On April 9, 2007, Oliphant was a guest on the Imus' morning radio show in the midst of the developing controversy. Imus had apologized for his comment before that show, and Oliphant explained his decision to appear on the show to the New York Times, saying "He said he screwed up and he was sorry."[7] On that evening's NewsHour with Jim Lehrer, Oliphant was critical of Imus' remarks, calling them "inexcusably horrible", but said "I don't think he should be fired."[8]
Oliphant, after declaring solidarity with Imus, announced that he would no longer appear on television or radio until Imus was reinstated to both his radio show and the MSNBC simulcast.[citation needed]