This article addresses the issue of contractual freedom. Using a comparative analysis between the Italian Civil Law system and the UK common law system, it analyzes the problem of the possibility for Court jurisdiction to intervene in front of inequality of collective bargaining power. The possibility to interfere with contractual freedom is also seen when the intervening party is not a judge, but one of the independent regulatory authorities. To prove this research the results are applied to a specific kind of contract, called Payment protection insurance (PPI), also known as credit protection insurance, which is an insurance product that enables consumers to guarantee credit repayment if the borrower dies, becomes ill or disabled, loses his/her job, or faces other circumstances that may prevent earning an income to repay the debt. Indeed, this type of contract results in an unequal bargaining.