John Oliver Is Betting His Emmy Award

When it comes to outlandish propositions, HBO talk show host John Oliver has an offer for Donald Trump that the Republican nominee probably shouldn't refuse. On Sunday night's episode of Last Week Tonight, Oliver made a hilariously convoluted bet with Trump that pokes fun to both the latter's lack of success with awards shows and his seeming incapability to accept defeat. In a segment on his Oct. 23 show, Oliver said he'd give Trump his Emmy if he admits defeat, a proposition that perfectly illustrates the absurdity of the former reality TV star's refusal to admit he's really ever wrong.

Referencing Trump's claim that the Emmy Awards were rigged against him when he didn't win for The Apprentice (repeated most recently at the final presidential debate by Hillary Clinton), Oliver offered an on-air wager to The Donald. The sarcastic bet Oliver made has some wild stipulations that, in Oliver's words, will allow Trump "to claim that he won something." Oliver said he'd bet that Trump won, meaning that Trump would bet on his own defeat — but that if Trump "wins" the bet (by losing the election), Oliver will give Trump one of his Emmys — presumably, the one he won in September for Outstanding Variety Series. It's not as if the British funnyman, who's won five Emmys (two of which he won for Last Week Tonight this year) will miss it much.

In characteristic fashion, Oliver explained exactly why an Emmy is so important to Trump:

It's a woman, it's gold, and it's proportionate to his tiny hands. It's basically Trump's ideal mate.

Oliver went on to joke that Trump appears to be "medically incapable of accepting that he's a loser," and therefore, his wager is necessary for the American people to get the closure we so desperately need with this traumatic and much-too-long horror film that has been the 2016 election season.

This is, of course, not the first time Oliver has directly addressed the Republican nominee on live television. In August, Oliver famously begged Trump to drop out of the race following the departure of his former campaign manager Paul Manafort. Oliver's pseudo-satirical proposal, like this more recent one regarding the Emmy, jokingly offered up a positive spin for Trump: if he were to have dropped out then, with 11 weeks until the election, he could have executed the biggest "gotcha!" in world history by proving just how capable Trump was of influencing the public without actually becoming president. With only two weeks until the election, this equally-absurd prospect seems somehow more humane and rational than for Trump to actually continue his scorched earth march towards the election on Nov. 8.