This study reviewed the trends and characteristics of media merger and acquisition cases in Taiwan, finding that the current related regulations are not implemented appropriately. Comparing the evolution of different drafts of the anti-media monopolization law, this study concludes that the latest draft remains too focused on traditional media and may be unable to effectively regulate online media. Moreover, rigid restrictions on mergers and acquisitions may discourage innovation and overseas competition. Rather than prohibiting mergers between media and banking or media and any other industries, having effective fit and proper ownership tests is the key regulatory factor. A draft that includes such measures alongside regulations to protect media workers’ rights, independent news rooms, and diversified financial sources of media productions can make significant strides toward resolving the media monopolization dilemma and safeguarding diversity of speech while preserving opportunities for media innovation.