If Hillary won there was no good outcome for him - either she’d fail, which would get blamed on him, or succeed, for which she’d take credit for being the uniter that he could never achieve.
Her “first woman” achievement would also irk him as that “first” relates to half the population, compared the demographic that gets tingles over his “first”.
And at best, he’d simply fade into irrelevance as Hillary took center stage, knowing that any critical comments he might hav could not be shared.
But with Trump winning and both Clintons on the outs, what could be better for him! He is no the defacto anti-Trump leader of the Democrats.
But a Trump victory means that most of his legacy will be undone and there is the possibility that some of his wrongdoings will be uncovered by the new Administration. It will interesting to learn what were in the secret side agreements to the Iran deal. Or the cover-ups in Fast and Furious and the IRS. Or where he was during Benghazi. Despite some personal glee Obama might take in a Hillary defeat, there is no doubt that a Hillary victory would have served him better.