I propose to look at how, over the last two decades, American’s views of Russian President Vladimir Putin have changed. I plan to look at archives from the Washington Post and Wall Street Journal, identifying the long-term trends as well as turning points. When Putin first came into power, America saw him as someone they could work with, a continuation of the tentative new democracy in Russia. George W. Bush famously met with Putin and “[got] a sense of his soul.” Seventeen years after Putin came into office, his commitment to Russian democracy is questionable as he prepares to run for his fourth term as president in 2018. His relationship with the US is rockier than ever, with congressional investigations into Russian meddling in the 2016 elections now underway. I want to look at how the news media has covered this shift and whether I can find key moments in that shift.