Third Month Mania: Round One Preview

The tournament to find Donald Trump's single greatest tweet begins.—what-is-the-greatest-donald-trump-tweet-of-all-time-
March is in full swing, and that means it’s time for Third Month Mania, The Daily Show’s answer to a certain bracket-based springtime sports competition. This year’s edition is one for the record books as Trevor and the team try to get to the bottom of one very important question: What is Donald Trump’s greatest tweet?

Before you call your bookie, take a gander at some of the key matchups as we near the end of the first round of voting:


Who can say which way this one will go? On the one hand: petty, baseless insults followed by (strangely) a compliment. On the other: a complete disregard for spelling.

It’s misogyny against misogyny as the Donald unwisely goes after not one but two female icons. But which tasteless and juvenile dig will reign supreme?


Good ol’ Trump’s never been one to go easy on politicians he dislikes, and both of these contenders show just how far he’ll take his grudges. It’s unlikely anyone else pays such close attention to Barney Frank’s nipples, or that any other modern president has ever called their enemies “dogs.”

Whether he’s in office or out, Barack Obama has certainly captured Trump’s imagination — not to mention his baseless paranoia. But those wiretapping claims are sure to face tough competition from Trump’s other equally outrageous (and racist) attack on his predecessor.


F. Scott Fitzgerald famously said, “The test of a first-rate intelligence is the ability to hold two opposed ideas in mind at the same time.” It’s certainly possible that Trump’s contradictory views on the Electoral College exemplify what Fitzgerald is talking about… or maybe they’re just conditional based on whether they benefit him at the time.

There’s so much to unpack here: the Donald’s signature germaphobia, his iconoclastic approach to spelling, his vague-yet-regressive views on women in the military. It’s anyone’s guess as to which tweet will win.


Donald Trump’s approach to the haters and losers is a masterful combination of disdain and reconciliation. On the one hand, he wishes them well and wants them to buy his neckties. On the other, he calls them “haters and losers.” If there’s a silver lining, it’s that one of these “losers” will emerge a winner this round.

So much mystery in such a small amount of text! Who’s the source of these tattoo rumors? Does the pope really settle his own hotel bill? Both tweets challenge the mind, but only one will be victorious.