The Sixth Amendment guarantees the right of a defendant to be represented by counsel, most importantly to have effective assistance of counsel. Evolving for nearly a century, the current state of the Sixth Amendment is a result of a historic and longstanding relationship that the Court has maintained with the Sixth Amendment resembling a tug-of-war of sorts, a back and forth that is arguably still going strong. Throughout this history the Court has refined what rights the Sixth Amendment entails as well as to what extent these rights should be provided. In accordance with Argersinger v. Hamlin, regarding the deprivation of liberty, indigents must be provided counsel if any form of jail time could result from a criminal proceeding. It will be argued that the Court has left open the possibility for future cases to arise in regards to the deprivation of property and importantly, it will be argued based on the evolution of the Sixth Amendment that such cases will lead the Court to extend this right to indigents facing penalties in the form of a fine.