Ted Cruz had his chance to derail Obamacare. Now it’s up to Internet trolls.

At least that’s the plan of Dustin Stockton, a top Tea Party strategist who sent out word Friday morning that he is organizing what he has termed “The Great American Troll-Off”—a chance for Tea Partiers to win cash prizes for tweaking the federal government.

The plan was launched in response to a program from the federal government that allows the curious—or the mischievous—to have questions about the new health-care law answered via live chat from trained experts through the healthcare.gov website.

“Apparently President Obama thought that it was a good idea to hire people to answer questions about Obamacare on live chat, seriously,” Stockton writes on his website. He then instructs readers to go over to the live chat at healthcare.gov and “document your live chat with a government agent.” Those who post the transcript on his site will be eligible for cash prizes, with $100 each going to the “funniest” transcript, the “most shocking response from the government,” and the “best use of trolling.”

“I don’t like Obamacare,” said Stockton, plainly. “So for me, it’s a win-win. If they are able to withstand the pressure and a lot of people get their questions answered, great. And if they can’t handle the pressure, it hurts Obamacare. “

The Tea Partiers’ hope is that the live agents get flummoxed and say something embarrassing, or at least that they give conflicting answers to the same question.

“If they are not in a position to answer the question in a consistent manner, then it does hurt Obamacare,” Stockman continued. “If they are giving misleading answers, we will expose it. And maybe we will get some headlines out of some of the answers. Something like—‘Even Obamacare Experts Don’t Know What Is Happening With Obamacare.’”

A “troll” on the Internet describes the type of commenter on web pages or chat forum who says something incendiary in order to get a reaction from fellow readers. As an editor at About.com put it, “Named for the wicked troll creatures of children's tales, trolling is purposely sowing hatred, bigotry, racism, misogyny, or just simple bickering between others. Trolls themselves are emotionally-immature users who thrive in any environment where they are allowed to make public comments, like blog sites, news sites, discussion forums, and game chat.”

For those who self-identify as such, Stockton believes they can be beneficial to the cause of derailing what looks to the Tea Party like a government takeover of the health-care system.

“You’ve conquered entire Facebook pages and gotten semi-celebrities to bite on Twitter, but are you ready to troll the biggest target of them all?” he writes. “If you said yes then get ready because it’s you versus the government and this time there are prizes to be won!”

In an interview, Stockton downplayed his troll-hopes, saying that he used the term more to get attention for the endeavor, and as a former call center employee himself at one point, he said he did not want anybody who answered questions at the health-care website to get in any kind of trouble.

“Unless it is really outrageous, I don’t want to get anybody fired. The poor call center guy, he is not responsible for Obamacare. The big thing I am trying to do is to get as many chat logs as I can to complete the universe of information.”

Stockton had his own go at the healthcare.gov help desk yesterday, and posted the exchange on his website. Oddly enough, he said that he actually found the exercise useful in a non-trolly kind of way. He asked if there would be criminal penalties for refusing to sign up or to pay a fine, and was told that there would not be, only that future tax refunds could be withheld. He asked about privacy concerns, and said he was impressed by the depth of the answer, even if he didn’t quite believe it.

“I was impressed,” he said. “I think if they are able to withstand the barrage on the Internet, new tools like this should be used to communicate policy changes. Whether I agree with the policy or not, this is the transparency we should be striving for.”