As a political organized/party leader Obama was largely unsuccessfully. He was great at running himself for the Presidency, but the party in general was left in much worse shape. First he tossed Dean's 50 states strategy and elevated mediocre leader such as Kaine for chair, then pretty much ceded control to the Clintonites. What I find particularly puzzling is the President being fine with his own party chair (DWS) fighting him over one of his signature policy decisions (Iran deal).
Yeah that's probably Obama's biggest mistake in terms of politics: he let the Clinton faction run the Democratic party into the ground.