The Labour Party has had a troubled relationship with constitutional questions. Its desire to restructure power relations and empower citizens has always run up against the need to use the power of the state to achieve its social and economic objectives. Although the constitutional reforms of the Blair years were genuinely radical in intent, the party left office accused of hoarding power and alienating citizens still further from the democratic process. As Jeremy Corbyn embarks on another quest to reinvigorate party politics and renew British democracy, this chapter seeks to understand what went wrong before. It identifies four obstacles to meaningful reform and concludes that a Citizens’ Convention on political reform offers the best chance of avoiding them in future. This would demonstrate that Labour recognises that it has been part of the problem and show that it is now willing to devolve decision-making on the biggest questions of all to citizens.