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Section 23-2 of the Korean antitrust law (the Monopoly Regulation and Fair Trade Act), a provision that prohibits specially related persons from raking in unfair advantages, was enacted to limit the private interests of family members of conglomerate presidents. This provision stipulates four types of conduct including tunneling in corporate law. However, the clause has semantic ambiguities that leave open the interpretation of its objects, scope, and application to specific cases. Since the new clause was put into effect, Korean Fair Trade Commission (hereafter “KFTC”) has mainly enforced against the violation of subparagraph 1 type, conducting transactions under terms that are substantially favorable to the terms that have been applied or judged to be applicable to normal transactions. Recently, KFTC has been actively investigating and sanctioning against the violation of subparagraph 4 types, conducting transactions without reasonably considering factors like transaction parties’ business ability, financial status, credit rating, technical skills, price, terms of the contract, or without comparing these factors against those of other enterprises. However, short of any precedents, applying subparagraph 4 of section 23-2 remains a challenge. This article reviewed legal issues and suggested a proper way to construe the phrase of reasonable consideration, substantial size, and unfair profits. First, lack of reasonable consideration is a necessary condition for a transaction to be considered a violation of the given clause. The term reasonable consideration is an abstract and open notion encompassing business ability, financial status, credit rating, technical skills, price, and terms of the contract. The act of comparing these factors with those of other enterprisers is typically seen as conforming to the reasonable consideration requirement. The Presidential Decree additionally requires relevant transactions to conform to a proper selection process. Yet, any company that belongs to an enterprise group can evade the stricture, not only regarding reasonable consideration but also with the proper selection process. In addition, reasonable consideration is not confined to procedural standards. Thus, given that a reasonable and substantial transaction was made, even if the procedural requirements are not fully met, a transaction can be seen as satisfying the reasonable consideration prerequisite. By extension, transactions should meet the substantial size requirement before it is considered a violation of the clause. However, what qualifies as a substantial size is hard to measure or fix. Relevant markets, a devolving entity’s turnover, the other party’s turnover, and competitors should be comprehensively considered to establish a variety of standards to guide the court. In the future, courts should specify the standard and scope of reasonable consideration, substantial size, and unfair profits that will play a key role in deciding what qualifies as a violation and the strength of evidence. Once these principles are established, the legislator’s intent to prevent specially related persons from gaining unfair advantages would be better reflected in the enforcement of the law. Consistently enforcing these rules will enhance the predictability of the application, and in turn, guide business entities better.