Since its release in October 2018, Red Dead Redemption 2 has generated considerable controversy. Redemption 2, Rockstar Games’ highly popular video game set in a sprawling open world that resembles America’s southern and western states at the turn of the twentieth century, has attracted criticism from players who have disliked the perceived political messages the game presents. With numerous interactions with people of color, Native Americans, and feminist (suffragette) characters, the game prompts players to engage with the ongoing effects of colonialism, sexism, and racism, as well as the rising problems of an industrial and financial capitalist society. As such, the game’s depiction of Gilded Age and Progressive Era politics has resulted in a large amount of online criticism from a group of traditionally white, male, right-wing players. This article argues that Redemption 2 utilizes the Progressive Era as a vehicle to capture and speak to the current political climate, and that it is the game’s dual relationship with the past and the present that has aroused animosity from part of the game’s audience. Ultimately, it demonstrates how contemporary mainstream progressive politics can be interpreted within and projected upon the politics of the Progressive Era.