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Like many fringe candidates, Stewart is running to make a point.

“I call myself an IED,” he said. “An Increasingly Embarrassed Democrat.”

He considers himself a libertarian, and hopes to overturn President Obama's signature piece of legislation, the Affordable Care Act. Along with his check, he brought stacks of $2 bills; he handed them to passersby, asking them to \"tell two friends\" about his mission.

With a small group of supporters, he plans to spread his message to a select group of states: New Hampshire and South Carolina, for starters.

“California is what I really have my eye on,” he told ABC News. “I think I could win.”

Stewart arrived at 8:02am, shoved his way past reporters, & put down his $1k. The bills are props; he paid by check. pic.twitter.com/jJgeGdLfdJ

— Brad Mielke (@TheBradMielke) November 6, 2015

He’ll have a long way to go. Most states aren’t as accommodating to lesser-known White House hopefuls. Filing fees are often more expensive – South Carolina’s is $40,000, for instance – and candidates are required to produce thousands of signatures to support their bids.

In many states, the decision about whether to allow a name on a ballot rests with the secretary of state.

Lucky for people like Stewart, William Gardner is easily convinced.

“He said, ‘Oh yeah, let’s get going. Do you have a check?’” Stewart recalled.

Eyes wide, he compared it to his home state of Connecticut. “The process of filing for president in New Hampshire is easier than filing to run for school board,” Stewart said.

Meanwhile, O’Malley can take consolation in being the second Democrat to file for the Feb. 9 primary.

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