When I consume coverage of politics, I often hear sports metaphors. I figured "Hail Mary" would be a popular phrase applied to Trump at this point in the campaign. In football, Hail Mary is a desperate pass. Certainly not a play with a high success rate. Political pundits seem to use the phrase to refer to political strategy--an act of desperation, a sort of last-ditch attempt to change the impending outcome in a contest. Here's a sample of results from my Google search of "Trump Hail Mary" (links to the articles are in the titles):
"Trump’s Breitbart Hail Mary is the sign of a flailing campaign, but it also represents a dying wing of the GOP" - Salon.com
"Trump's Mexican Hail Mary" - Commentary Magazine
"Donald Trump's Hail Mary: A Meeting With House And Senate Republicans" - Talking Points Memo
"The Hail Mary Gamble of Voting for Trump" - Washington Post
"#NeverTrump Has a Hail Mary Plan to Block Trump" - Mother Jones
(First sentence is: "Donald Trump’s critics said his hastily arranged visit to Mexico was an act of desperation, a Hail Mary pass, the sign of an erratic campaign.")
"Trump might already be out of time" - Politico
(Final sentence of the story is: "But with Trump pulling in just 1 percent of African-American voters in Pennsylvania, many political observers view the sinking candidate — and his Hail Mary attempt — as the one with little left to lose.")
There are a few results that come up with a Google search of "Hillary Clinton Hail Mary," but there are more results for the search "Hillary Clinton run out the clock."
Hillary Clinton’s run-out-the-clock strategy - Politico
"Election Update: It’s Too Soon For Clinton To Run Out The Clock" - Five Thirty Eight
"Is Clinton running out the clock?" - Washington Examiner
(This story is from January 2015 -- she's been running out the clock for a long time, eh?!)
Still a few months remaining in the campaign, so I suspect there will be more Hail Marys and clock management to come. Also be on the lookout for fumbles.