WATCH: CNN Guest Rips Trump Over Weekend's 'Deer in the Headlights' Performance This Weekend

Donald Trump has had things rigged for him pretty much his entire life. He grew up wealthy, attending private schools and the University of Pennsylvania. Right out of college, he stepped into a cushy job and eventually inherited his father's business empire. 

The former President tends to avoid places where he might be booed and typically only attends sporting events if they're in 'safe' places. Which made his decision to speak at the Libertarian convention a little bit curious. During an appearance on CNN, Democratic strategist Maria Cardona discussed how Trump handled the situation. 

Host Jim Acosta noted, "[The campaign] is very careful about keeping him away from this stuff. And this just sort of blew up in his face."

Cardona then jumped in, "That’s what’s so surprising for a campaign team this time around that is very focused on making sure that he doesn’t get this kind of reaction, and I think there’s going to be some hell to pay within the campaign staff. He looked discombobulated, he looked redder than usual, sweaty, deer in the headlights because this is not the kind of reaction that he normally gets."

Watch the clip here

The former Clinton adviser also noted that the Trump campaign should have realized that this wasn't a good idea, saying, "Donald Trump’s agenda and his policies are the furthest thing from Libertarian that you can get."