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Despite Asian Americans’ general success in socioeconomic attainments and acculturation, it hardly translates into their political representation. They are politically most underrepresented and least likely to hold elected office among all racial groups. This paper addresses this phenomenon by studying Asian American political candidates’ and organizers’ experiences when running for office. Through 96 in-depth interviews with Asian American candidates and political organizers in Houston, Texas, I found out that they are trapped by what I called the “Asian American unelectable paradox.” They are consistently confronted with forever foreigner discourse from non-Asian American voters who distrust Asian American candidates and do not believe they will represent the American interests. The experiences of racism prompt them to think Asian American voters should unite and support Asian American candidates as a group. However, the racial lumping of Asian Americans creates a group of heterogeneous Asian American voters that do not always prioritize their Asian American identity. These candidates and organizers thus believe Asian American candidates could hardly mobilize any votes based on their racial status, and they are unelectable among both Asian American and non-Asian American voters. To overcome the Asian American unelectable paradox, these candidates and organizers would deracialize the campaigns, removing the Asian identifier and passing as White candidates, or they would spend extra effort proving their Americanness. This article debunks the literature on the assimilation of Asian Americans and illustrates how the racialization of Asian Americans manifesting in electoral politics reinforces their marginalization in the formal political process.