As President Barack Obama’s historic term in office winds to a close, his legacy remains unsettled, and so does his presence within hip-hop culture. When he emerged in the mid-2000s as a talented Illinois senator, Chicago rapper Common rapped on Jadakiss’ “Why” remix with eerie prescience, “Why is Bush acting like he trying to get Osama/Why don’t we impeach him and elect Obama?” Four years later, as Obama capped a historic run to the White House, he became a pop culture meme celebrated on Jeezy’s “My President is Black” and Nas’ “Black President.” But there was also an emerging leftist critique against the Democratic president– see Mr. Lif’s “What About Us” and dead prez’ “Politrikks” – and that criticism only increased as he battled with an implacable Republican Congress, failed to prosecute Wall Street executives responsible for the 2008 economic recession, struggled to extricate the country from wars in the Middle East, and tried to bring the country out of an economic recession.Only time will tell which image resonates the most: the pop icon from Jidenna’s “Long Live the Chief” who shifted the country towards steady but incremental progress, or the establishmentarian whose policies resulted in insubstantial trickle-down gains for the working class, leading African-Americans like Ice Cube to declare that “Everythang’s Corrupt.” The arrival of his Republican successor, real estate tycoon Donald Trump, only muddies the waters of how we’ll eventually perceive this historic figure. As YG raps on “FDT,” “[Trump] got me appreciating Obama way more.”