This study analyzes the contrarian investment strategy in GCC’s emerging market, specifically focusing on Kuwait’s tax-free economy between January 2008 and December 2022. Through an empirical investigation, we examine the impact of the January effect on contrarian returns. Our findings show that the contrarian strategy yields positive, risk-adjusted, and statistically significant returns across various periods, which demonstrates its effectiveness, even when excluding the returns of January. Additionally, our analysis provides robust support for the overreaction hypothesis in the Kuwaiti market, showing that contrarian returns persist for up to 4 years after the formation period. This study makes a significant theoretical contribution by exploring the underlying drivers of contrarian returns in a tax-free context, challenging traditional assumptions about the sources of these returns, and providing insights into investors’ behavioral dynamics in an emerging market setting.