The 2016 election has not been kind to Jeb Bush. He might have started 2015 as the favorite to take the Republican nomination, but after polling terribly for months he could only manage a piddly 6th place in last week’s Iowa caucus, and his chances in the first primary in New Hampshire today aren’t much better. (The last time we checked, Five Thirty Eight puts his chance of winning at about 3%.) What’s made it worse is the fact that, in the age of new media, Bush is a terrible campaigner. Everything he does feels painfully forced—from his overly-enthusiastic Jeb!™ logo to his over-rehearsed debate quips—and awkwardness radiates off him like a teenager whose whole family just walked in on him jacking it.

As Jeb’s poll numbers slip, so do his spirits, and he now resembles a broken man, shuffling his way through the motions as he desperately prays for a miracle—or his PAC money to finally run out. Can he turn it around? Maybe. But until then it’s not going to be pretty. Here, are the 15 saddest Jeb moments we’ve had to witness so far. Keep checking back for updates between now and November—although we can only assume he'll be put out of his misery long before then.

July 16, 2015

Starred in this painfully unnecessary ode to modern technology.

July 16, 2015

As a result, was the star of maybe the most important political Vine of all time.

July 17, 2015

Released a video of himself struggling to put on a hoodie.

September 3, 2015

Gave a speech that was so boring a woman behind him actually fell asleep while he was talking.

September 15, 2015

Was waaaaay too pleased about the fact he made a joke in a debate that didn’t suck.

Note the achingly overenthusiastic low-five that followed it up. You can almost hear him internally screaming “nailed it!”

October 28. 2015

Attempted to strike a blow at Marco Rubio, his former protégé, about Rubio's voting record and missed spectacularly. .

November 9, 2015

This. (Spoiler alert: he didn't.)

November 9, 2015

Thought it would be a good idea to enthusiastically say he’d commit infanticide.

November 9. 2015

Became the butt of a million “baby hitler” jokes.

December 15, 2015

Seemed physically incapable of making the valid point that he, Florida’s first two-term Republican governor, is a better candidate for President than the former host of The Apprentice.

January 28, 2016

Forced himself to feign amusement at his own painfully low expectations.

January 29, 2016

Personally hugged a voter when they told him he might (note: might) swing their vote.

February 3, 2016

Begged an audience of supporters to “please clap.”

February 7, 2016

Wore shoes that were held together by tape.

February 9, 2016

Kicked out of his own campaign event.

Jeb was giving an impassioned speech at a Rotary Club in New Hampshire when his hosts kindly asked him to leave while he was still speaking. If you keep watching the video you'll see it was likely because Jeb was running behind schedule, but that didn't make the encounter any less awkward.