Modern democracies rest on a foundation of values essential to their prosperity. Two of those values are freedom of speech and political equality. To many, these values appear to coexist effortlessly. However, what this thesis aims to expose are some of the problems that quickly arise when attempts to interpret the values fail. The thesis investigates a specific US Supreme Court ruling called Citizens United. The ruling enabled corporations and unions to use their own treasuries for unlimited independent political expenditures. Previous laws that prohibited such corporate and union expenditures were deemed unconstitutional by the Supreme Court for violating the First Amendment’s right to freedom of speech. The ruling also paved the way for another court ruling in the US called SpeechNow.org. Facilitated by the two court rulings the so called Super PACs and 501(c)(4) organizations could receive and spend unlimited money to expressly support or oppose political candidates and parties in American elections. With an analytical framework consisting of John Rawls’s theories the Veil of Ignorance and the Difference Principle a conclusion concerning Citizens United’s righteousness can be made. The thesis concludes that the Supreme Court based its ruling on a misinterpretation of the value of freedom of speech and that Citizens United resulted in greater political inequality in the US.