Numbskull Negotiator

"Flying Dutchman: You give me back the sock and I'll give you three wishes Patrick: Make it five. Flying Dutchman: Four. Patrick: Three, take it or leave it."

- SpongeBob

Negotiating is an art and science that, if done well, can stop wars, ensure bargain prices at auctions, and make all kinds of deals in general go in your favor.

If done by… someone not cut out for it, things can backfire horribly for the negotiator, often in incredibly hilarious ways depending on the deal in question. The character does not need to be stupid all around, just terrible at negotiating.

Advertising

 * A car commercial advertising that stated they were selling their cars at a non-negotiable price had a customer that was this. His starting offer was the price that the dealership was offering, and seemed to be willing to negotiate, the salesman probably could have worked him up higher than what the advertised price was. To make it even worse he was proud of himself of how well he did.

Western Animation

 * The police negotiator in Fun with Veal South Park, he gives the boys a lot of weapons in a hostage situation for a baby cow.
 * Amy in Futurama when she gets a car, possibly because her wealthy parents are paying for it (and thus didn't really care).
 * In the SpongeBob episode Squeaky Boots, Mr. Krabs suckers Spongebob into bidding for a pair of typical boots he got stuck with. Spongebob offers a bid, Mr. Krab tries to accept, and then Spongebob adds onto the bid, this goes on till Mr. Krabs forcefully stops Spongebob from bidding to prevent himself from getting "a heart attack".
 * In The Amazing World of Gumball episode The Origins we see Gumball's Bumbling Dad negotiate. Unsurprisingly, he fits this description.

Real Life

 * Purposely invoked by the Polk administration before the Mexican-American War. Polk sent someone to give the Mexicans a negotiation offer they'd clearly refuse, gave the diplomat in question a fancy title when they were of little importance, and they basically botched the job that had little chance of succeeding anyway since Mexico's current leader had little interest in negotiating anything, especially after the Alamo. Of course, this was part of Polk's goal of provoking the Mexicans into giving the U.S. an excuse to go to war with them.