Now Lewandowski serves as the campaign manager for Donald Trump's campaign, putting him on the other end of the argument as taxpayers in cities and towns across the country pick up the hundreds of thousands of dollars in additional costs for the mega-rallies of the GOP front-runner.
For instance, at Trump's rally in Long Island on Wednesday, the county of Nassau paid at least $300,000 in security expenses, according to Police Commissioner Thomas Krumpter.
In his home town of Windham, Obama's presidential campaign racked up $5,490 worth of expenses for the town for ten firefighters, five police officers and one dispatcher.
Lewandowski, then the state director of the Koch-backed Americans for Prosperity, recorded his own robo-call, demanding that the town be reimbursed. He also solicited the town council to take up the issue.
The town, which has an annual budget of about $15 million, spent more than half of its August 27, 2012 meeting - one of only three that month - on the issue.
"As both a financial watchdog and a resident of Windham, I believe that no taxpayer resources including time, personnel or monies, should be used to support campaign activities for any candidate for public office," Lewandowski wrote in a statement at the time.
Lewandowski's close friend, and chair of the town's legislative body, Bruce Breton, led the effort among the five members.
"It was kind of a big issue," Breton said in an interview Thursday.
Kathleen DiFruscia, also a selectman on the board at the time, was opposed to the effort. "It was intense for a short period of time," she said.
She also said it was a purely political move on Lewandowski's move.
Of course, Trump's campaign isn't the only one where cities pick up campaign costs.
Chief Gerald Lewis, head of the police department in Windham at the time, said the town had not billed any other candidates that campaigned there and additional costs had been "absorbed via overtime," according to minutes of the meeting. Most presidential candidates stop in Windham, a town of 13,000 in a critical primary state. One speaker at the town meeting noted that the unwritten, no-pay policy dated back to President Gerald Ford's visit in 1975.
Lewandowski lost that effort. The board voted 3 - 2, opposing sending the President Obama an invoice. And despite suggestions to do so, the board never drafted written policy for candidate-incurred taxpayer-funded expenses.
NBC News reached out to the Trump campaign for comment but has received no response.
This story first appeared on NBCNews.com.