When Naomi Osaka became the first tennis player representing Japan to win the US Open in September 2018, it was not her superb performance on court but her tear-filled “apology” after the game that caught the attention of the media and the public. While the U.S. media mostly focused on her opponent Serena Williams missing her 24th grand slam title and the controversial ruling by the judge, Japanese media emphasized that Osaka “apologized” to American fans for the outcome rather than openly embracing her hard-earned victory. Specifically, it was her words “I’m sorry it had to end like this,” uttered in English and translated into Japanese by the Japanese media, that caused a heated public debate in the days that followed. Some media initially translated her words as 勝ってごめんなさい [Sorry that I won] which instantly became a target of social media criticisms, with many claiming that the word “sorry” in English does not necessarily mean that the person is apologizing. Despite such criticism, most of the mainstream media in Japan kept using various words of apology to fit the “Osaka is very Japanese” narrative they were trying to spread, demonstrating that interlocutors can manipulate levels of apology when translation is involved. Previous research has found that apologies can vary significantly due to cultural differences (Maddux, Kim, Okumura & Brett, 2012; Oi, 2015). In East Asia in particular, levels of apology expressed by political leaders have often been at the centre of diplomatic attention, as was the case in Japanese Prime Minister Abe’s statement commemorating the 70th anniversary of the end of World War II, which was translated into multiple languages and scrutinized around the world (Matsushita & Schäffner, 2018). Against this backdrop, the present study examines how apologies by numerous newsmakers in the past decade have been translated by using a corpus of interpreter-mediated press conferences held in Japan. Although the corpus itself, which utilizes approximately 400 hours of videotaped press conferences held at the Japan National Press Club since 2009, is still under development, initial findings revealed that interpreters tend to adjust apologies by changing their intensity when interpreting, especially where politically sensitive topics are concerned. The present study analyses cases of both “overplay” and “downplay” by the interpreters by applying the concept of risk management (Pym, 2015; Matsushita, 2016). Using the risk management categories identified in Pym and Matsushita (2018), it illustrates how cultural differences in expressions of apology often prevent literal translation, leaving room for manipulation during the interpreting process to avoid, mitigate, transfer, or take risk.