Steve Bannon, who rose to power as Breitbart News chairman and Donald Trump’s strategist on a wave of anti-Wall Street fury, spent much of the last decade-and-a-half using many of the complex financial mechanisms employed by the largest financial services firms as a board member and investor in penny-stock ventures.

Court filings and corporate records reviewed by POLITICO show that during this period, long after Bannon’s stint with Goldman Sachs in the 1980s, these penny-stock firms employed some of the complex corporate maneuvers favored by financial masters of the universe — trans-national acquisitions, reverse mergers and asset purchase agreements — though on a much smaller scale. Most of the companies failed to take off, often in the throes of legal troubles, in the years before Bannon emerged as a populist critic of financial wizardry run amok and failures to prosecute Wall Street executives.

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“It’s just sheer hypocrisy,” said Jaime Harrison, chairman of the South Carolina Democratic Party and a candidate for chairman of the Democratic National Committee, of Bannon’s recent stances. “It’s: ‘Do what I say, not what I do.’”

Bannon’s partner in a series of these ventures was a close friend and ongoing business associate with whom he shares a voting address in Florida. (Bannon registered at the address following news reports that he was previously registered to vote at a vacant property.)

Before Bannon shared a home address with the man, Andy Badolato, the pair partnered in a series of business ventures that included homeopathic nasal sprays, cosmetics and fragrances. The ventures came during an overlooked chapter of Bannon's career, in the years leading up to the last financial crisis, when Trump’s chief White House strategist dove into the world of penny stocks.

Badolato has been the defendant in numerous lawsuits related to his personal finances. Though he was never charged, Badolato was also implicated by the government in a stock manipulation scheme that grew out of one of Badolato’s ventures with Bannon and put two men in prison. Another one of Bannon’s colleagues in these ventures, Seattle attorney David Otto, was slapped in an SEC settlement with a six-figure fine and a five-year ban from participating in the offering of penny stocks for his alleged role in an unrelated stock fraud scheme.

Bannon, who declined to comment through a spokeswoman, emerged unscathed from the murky milieu of the pink sheets — where companies that do not make it onto major stock exchanges trade — climbing to conservative media mogul-dom and now the White House.

“The guy is smart and knows exactly what he is doing,” wrote entrepreneur Mark Cuban, a vocal critic of Donald Trump who has dealt with Bannon in the purchasing of film distribution rights and met with him in New York on Tuesday, in an email.

Bannon’s foray into the high-risk, high-reward world of penny stocks began around the turn of the millennium. The foray spanned multiple firms, and Bannon, as a veteran Wall Street and Hollywood dealmaker, would often serve as an advisor in his role as board member and shareholder, according to his associates in some of the ventures.

Todd Van Siclen, a former associate at Otto’s law firm who was involved in some of the ventures, said Bannon mostly stayed away from the day-to-day operations. “People such as Bannon, their role with those companies was more involved with review, consultation – as opposed to being hands on,” he said.

One of those ventures was Donna Messenger Corporation, a cosmetics business registered in 2003 in Delaware that included Bannon, Otto and Badolato on its board, according to corporate filings.

Another was SinoFresh, a maker of homeopathic nasal sprays. Ahead of a 2003 IPO, Badolato, a Sarasota-based entrepreneur, began providing SinoFresh with financial advice and Bannon and Otto joined its board, according to corporate records and legal filings in Florida. But their partnership with the company soon soured.

The company’s founder, Charles Fust, uncovered an alleged scheme by Badolato to rob him of a million shares of stock by putting it under the control of a corporation registered in Belize and controlled by a Costa Rica-based businessman named Jonathan Curshen.

Fust and his allies responded in early 2004 by attempting to remove Bannon and Otto from the company’s board, citing their ties to Badolato, according to an SEC filing. Bannon, Otto and two relatives of Badolato retaliated with a lawsuit alleging that Fust used company funds to purchase an engagement ring, among other misdeeds. Bannon and Otto were reinstated to the board, but a court-appointed independent expert found that the allegations against Fust were baseless.

The independent expert also found accounts of the disputed shares given by Badolato and Curshen – who ran a firm in Costa Rica that offered offshore financial services – unconvincing and riddled with inconsistencies, and awarded the shares to Fust, according to court records in Florida. SinoFresh was roiled by the dispute and performed poorly. Eventually its stock stopped trading altogether in 2011.

Bannon, Badolato and Otto moved on. In 2005, they formed a company called “Bio-Flavorance Technologies and Research Inc,” which owned rights to patents for the flavors and fragrance industry, according to its press release.

In January 2006, the company was acquired by Industrial Biotech Corporation, or IBOT, via an asset purchase agreement, and issued a press release. IBOT had been founded four months earlier, and was registered to the same Sarasota office suite that Bannon and his partners had listed as their address in the Bio-Flavorance filing. Following the acquisition, Badolato became chairman and president of IBOT. Otto and Van Siclen joined its board.

IBOT was soon rocked by scandal. In 2008, Curshen and a Florida-based stock promoter were arrested after attempting to enlist an undercover FBI agent posing as a stock broker in a scheme to manipulate IBOT’s stock. The fraud, called a pump-and-dump, involved artificially raising the price of IBOT’s stock by faking organic trading activity and bribing brokers to buy the stock for wealthy clients at inflated prices. Curshen and the stock promoter were convicted of fraud and sentenced to prison terms.

Generally, pump-and-dump schemes require the cooperation of whoever controls the trading shares of the company targeted. Badolato was never charged, but in court filings both the government and Curshen describe him as a co-conspirator and the primary beneficiary of the scheme.

Curshen has asserted in court that proceeds from the scheme were deposited into an account controlled by Badolato.

In a motion opposing a 2012 attempt by Curshen to vacate his guilty plea, lawyers for the Justice Department asserted, “Badolato controlled all of the free trading shares of IBOT. … [the Florida-based stock promoter] and Curshen agreed that they could help Badolato promote the IBOT stock in exchange for a sizable payment. Over the course of several meetings, Curshen, [the promoter], and Badolato negotiated the payment structure. They agreed that all three million IBOT shares would be sold by [Curshen’s firm]. Once the shares were sold, they would deduct the expenses incurred from selling the stock (i.e., bribes, promotional materials, mailers, etc.). Of the remainder Badolato would take half, and Curshen and [the promoter] would each take a quarter.”

Badolato declined to comment on any of his ventures through his lawyers. In a letter to POLITICO, the lawyers, Wil Florin and Thomas Roebig Jr., wrote, “Mr. Badolato as you know is a private figure. He has no interest in entering into a public discourse on any subject related to him . . . He is a single father and a well-liked and respected businessman in the Tampa area.”

The lawyers added, “Mr. Badolato, as you know, has never been convicted of a felony in any court.” Neither Badolato nor Bannon responded to questions about what relationship, if any, Bannon had to IBOT after the company purchased Bio-Flavorance.

Bannon, meanwhile, had on embarked another business venture with Otto. In 2006, he became chairman of a business called Veritas Solutions, which Otto had founded two years earlier. Veritas acquired SARS, a logistics firm, and Bannon became chairman of that company in October 2007. Also in 2007, SARS went public through a reverse merger by acquiring the multimedia design firm Mycom. That same year, it merged with a UK firm Andronics, which remotely monitored the levels of liquefied petroleum tanks, and the next year acquired Jinkhold Ltd., creating a firm called SARS Andronics, according to corporate filings with state, federal and UK regulators.

The company aimed to become a service provider to the gas industry, but SARS became embroiled in a legal dispute and then fizzled. In May 2008, a software vendor sued SARS, alleging it had breached its contract by hiring away a developer to steal its intellectual property, then hiding the move by employing the developer through another corporation and providing him with an email address under a false name. SARS countersued the vendor, and Bannon resigned from the company’s board that July. Ultimately SARS agreed to pay the vendor $90,000 in a 2011 settlement.

Otto said the company never took off, chalking the failure up to an “expectation of a relationship with BP that never materialized.”

In 2011, Otto agreed to pay more than $200,000 and he and Van Siclen accepted a five-year ban from offering penny stocks to settle allegations that they engaged in a pump-and-dump scheme by promoting fake products for a company called MitoPharm Corporation, according to a statement from the SEC. (There is no indication that Bannon or Badolato were involved with MitoPharm.) Otto and Van Siclen did not admit wrongdoing, and Otto said he settled because he did not want to continue paying a lawyer after racking up more than a million dollars in legal fees.

During his years working with Bannon, Otto said he saw no hints of the flame-throwing populist he would become. “He was certainly sophisticated and capable. He seemed like he understood the private equity, if you will, type business, the leveraged buyout business. He understood the financing business, the capital markets business and understood how difficult it was for early stage businesses,” Otto said. “We never got into any conversations about the systemic problems with Wall Street or the economic nationalism stuff.”

Badolato filed twice for chapter 7 and twice for chapter 13 personal bankruptcy between 2005 and 2014, according to federal court records. He has also become a local Tea Party activist in Sarasota. He has maintained his close relationship with Bannon, appearing on panels with him and contributing sporadically to Brietbart.com, where he has written on Trump’s odds in betting markets and the availability of Christmas decorations with overt Christian messages. He also partnered with Bannon in the production of political documentaries, helping to market Bannon’s 2011 film about Sarah Palin, then serving as an associate producer on “Occupy Unmasked” and “District of Corruption.” Most recently, Badolato worked as an associate producer on Clinton Cash, the Bannon-produced documentary based on Peter Schweizer’s investigations of the Clinton Foundation and released in July.

Bannon, meanwhile, has steadily climbed the ranks of outsider conservatives in recent years, projecting a radical populist worldview and building Breitbart into a media force to be reckoned with.

In 2010, he wrote, directed and produced “Generation Zero,” a documentary about the financial crisis that attributed it in part to large investment banks converting from partnerships to publicly traded companies, encouraging reckless behavior because the firms’ leaders were no longer personally liable for the actions of their business partners.

In 2013, he reportedly described himself as a “Leninist” at a book party on Capitol Hill, though he has said he does not recall the conversation. And in a 2014 lecture transcribed by Buzzfeed, Bannon, commenting on the financial crisis, condemned a system that allowed savvy elites to engage in complex financial machinations without any consequences for their misdeeds.

“It’s all the institutions of the accounting firms, the law firms, the investment banks, the consulting firms, the elite of the elite, the educated elite,” he said. “They understood what they were getting into … And they’ve never been held accountable.”