We had a very good chance. Sanders was grabbing the support of disenfranchised GOP voters that didn't like the insanity of their party, independents, and progressives. Sanders, with Warren, simply needed to attack the establishment. Warren barely done it, knowing she'd get massive flack from women and punishment from Hillary if she'd won, and Bernie was just too nice to attack the establishment president, even when Obama left a gaping opening in his armor to do it. He didn't want to confront the Black shield over pragmatic Obama.
So here's what the "chess master" Obama left on the board for us:
Rooks: Secretary of Defense has always been Republicans, and our policy is to keep the ME at war for oil interests. -1 rook. He stopped the Iran bullshyt leading to war, and kept Israel from taking the region +1. His FBI Director is a Republican who is strongly against police wearing cameras, even if they're killing Blacks, even of they're sleeping in cars, and they monitor everyone, not just Muslims -1 Knight. The media is solely in the pocket of the establishment, and keeps the GOP in the game by not asking them about the cost of their policies or attacks on women's biological rights, as well as calling any progressive agenda insane or short-sighted without deliberation -1 knight. The Knights are the most mobile, and could be used to affect change if used the right way.
Obama doesn't give a damn about unions, and he has strong "keep the faith, change will be very slow and painful" Black religious and White female support -1 bishop. Progressives and others who know we can get change with the right reforms and actually playing chess and doing it to win, as well as the country is actually liberal +1 bishop.
Obama is very likely going to get a conservative justice passed, even if it looks like the person has liberal principkes, but that justice will always be anti-union, and against getting money out of politics and can effectively render any progressive legislation not Constitutional if challenged for 10 years at least -1 Queen.
Half of the Democrats support Obama and doesn't care about the legislation he passes, just the optics of another great speech and his feigned victim hood when he's actually throwing games -4 pawns.
So we have a bishop, rook, 4 pawns, and the king (liberal principles that Democrats claim to serve), against the entire GOP really (someone else can analyze their side).