On at least four occasions, MSNBC’s Chris Matthews mocked Sarah Palin for how he felt she’d do if she were ever on the hit television game show Jeopardy!.

In a delicious example of instant karma, the self-proclaimed brainiac got his chance to show America how smart he was in a special “Power Players” version of the show Monday, but came up quite short finishing dead last with the paltry sum of only $2,300 (video follows with transcribed highlights and commentary):

For those that missed it, Matthews was matched up against CNN’s Lizzie O’Leary and former Obama White House press secretary Robert Gibbs.

Quite comically, the MSNBC anchor’s first gaffe came when he couldn’t even correctly request an answer to a question.

“Let’s go back to, what is ‘Crossword Clues E?’ I mean, I’m sorry, let’s go $200 for the category ‘Crossword Clues E.’”

Matthews appeared to have his Joe Biden thinking cap on.

Host Alex Trebek finally read the answer, “At ____, soldier! Four letters.”