Jeb Bush bowed out of the race for the 2016 Republican presidential nomination on Saturday night, putting to an end one of America’s most prominent political dynasties and, frankly, one of the saddest campaigns in recent memory. Below, a look back at seven of the most awkward moments from Jeb’s bid for the White House.

Jeb!
Perhaps we should’ve seen it coming. In what appeared to be an ill-fated attempt to distance himself from the baggage that comes with the family name, the former Florida governor’s official campaign logo effectively replaced “Bush” with an exclamation point. It was quickly, and widely, mocked....

Baby Hitler
A month later, Bush established himself as the leading pro-time-travel-in-order-to-kill-an-evil-dictator candidate in the 2016 presidential race, saying he would gladly travel back in time in order to kill baby Adolf Hitler, given the opportunity....

‘Please clap’
At a town hall event in New Hampshire earlier this month, the former Florida governor and Republican presidential hopeful asked attendees to “please clap” after his call for the next commander in chief “to be a lot quieter” was met with silence.