Over the past decade, the scope of debates in Saudi media outlets have narrowed significantly, with even relatively mildly critical statements relegated to anonymous Twitter accounts or exiled activists. These changes have been hard to observe outside the Kingdom, however, due to academic assumptions that media outlets have been effectively controlled by the Saudi state for seconds. This paper seeks to establish the agency of a particular class of media professionals—op-ed writers—in either resisting, cheerleading, or withdrawing from new discourses of legitimation promoted by now-Crown Prince Mohammed bin Salman. Across three newspapers with different orientations toward central political authorities in the Kingdom (Al-Watan, Al-Riyadh, and Okaz), close reading of op-eds reflecting on the role of columnists in Saudi society identifies a number of writers affiliated with all three papers who viewed themselves as providing critical feedback to state institutions, even while asserting their loyalty to the Saudi state and political system. However, the murder of critical columnist Jamal Khashoggi in October 2018 did not have a uniform effect on op-ed content, as we might expect if media production in Saudi Arabia is centrally controlled. Instead, op-ed writers of different orientations reacted in different ways: those who generally functioned as government “cheerleaders” even before the Khashoggi murder maintained or increased column space devoted to praise of Saudi leadership and officials, while those who tended to criticize government performance in the earlier period either ceased writing or turned to less political topics. These findings demonstrate the chilling effect of overt physical repression even in a constrained media landscape such as Saudi Arabia’s, while also pointing to the challenges individual writers face in navigating the Kingdom’s shifting redlines.