We address how Kanye West’s negative scandal would have an impact on the Yeezy Boost products’ price premium. The price premium is a good measure to track the consumers’ preference towards the brand. For the methodology, we use the difference-in-differences to see the change in the price premium when the repeated scandal and apology occur. Before using difference-in-differences, I used propensity score matching (PSM) to match each control group to treatment groups. We handled two big Kanye West scandals that happened in a short period of time and apologized for two previous controversies. These events are seen as shocks in difference-in-differences methods and cause a change in the price premium. The price premium after the apology has been shown to be relatively lower than before, and the second controversy has had a more negative price premium compared to the first controversy. It appears that the inappropriate apology at the wrong time worsens the brand image.