Last week, Mayor Muriel Bowserbailed on “emergency” rule-making that would have allowed the controversial company Digi Outdoor Media to keep 15 digital signs it had installed at eight prime downtown locations without necessary permits.

Such a play, had Bowser gone forward, would have thwarted D.C. Attorney General Karl Racine, who sued Digi Media last year and obtained a temporary injunction that halted further sign installation. A D.C. Superior Court judge will decide whether to impose a permanent injunction.

To protect an $18 million investment from Australian firm Blue Sky Private Equity Ltd., Digi now must persuade the D.C. Council to enact legislation that similarly would negate Racine’s enforcement efforts.

But the question remains: What was Bowser thinking in the first place?

As NBC4’s Harry Jaffe reported last week, the mayor had a draft rule ready to go that would have allowed Digi to keep the signs it had installed before the Department of Consumer and Regulatory Affairs imposed restrictions last August. Bowser’s move came on the heels of “emergency” legislation introduced in December, then withdrawn, by Councilmember Jack Evans, who similarly was willing to undermine Racine.

Feigning ignorance of “the details” of Racine’s lawsuit, Bowser told television reporters last week that she had authority to “change the rules” if she wanted to. But she changed her mind instead. “We cannot comment on ongoing litigation that relates to the head of Digi Media, who took investor dollars in a scheme to affix illegal signs throughout the District of Columbia,” Bowser spokesman Kevin Harris said last week.

That company head would be billboard industry veteran Don MacCord.

MacCord comes recommended by Evans, whom he has known for 20 years, and is represented by lawyer-lobbyist David Wilmot, a friend, neighbor, and golf partner of top Bowser aide Beverly Perry, whom the mayor calls her “boss.” In seeking to develop goodwill in D.C. political circles, MacCord and his associates have bundled campaign funds for Hillary Clinton along with Evans and developers with ties to Bowser, and contributed directly to D.C. Council members and candidates along with Wilmot, who is known in some circles as “The King.”

Loose Lips has been monitoring the digital sign drama for months, and can’t help wondering how Bowser went from the brink of foiling Racine on behalf of a company whose executive has ties into her office, to publicly calling out that executive for taking investor money and scheming to break the law. Even stranger, Bowser once sided with Racine, who is arguing in court that Digi Media’s signs violate the law.

It’s hard to say with the secretive Bowser administration, but when LL looked for answers, some troubling history emerged.

Digi wants to install 52 signs at 20 different locations, and projects $800 million in taxable revenue. But the signs and the company’s business approach have alienated civic groups and drawn fire from major advertising companies like Clear Channel and Outfront Media, which complain that Digi broke the rules by installing signs it knew were illegal.

Industry sources say Clear Channel and Outfront are not direct competitors with Digi. Whereas those companies specialize in outdoor digital billboards and signs, Digi relies on what it says is an exemption from outdoor sign restrictions because its signs are installed underneath building facade overhangs.

According to the trade publication Billboard Insider, Digi stands to make big money, as its signs are part of a flexible network that can generate two or three advertising “flips” per minute. But it’s taking a heavy risk, the online trade rag says. “Insider’s take: This case reminds Insider of the company in Atlanta which installed a 14-by-48 billboard inside a building to evade sign rules. A creative interpretation of the regulations, but Insider wouldn’t want to risk money on it.”

A review of court records from around the country suggest that MacCord’s investors, if not Bowser and Evans, have reason to reconsider that risk.

MacCord is a major player in the outdoor advertising industry, according to his biography on the Initiative for Global Development website. With 20-plus years of experience, he has an extensive network of local and national political contacts, has developed outdoor signage in New York, California, Arizona, and London, and has invested in emerging markets such as Tanzania and Chile, his bio states.

Over the last decade, he also has gone into debt collection, passed a bad check at a Las Vegas casino, incurred a state tax lien, been foreclosed upon, and breached a contract and a lease, according to court records from California, Maryland, Nevada, and Washington state. D.C. court records show that a 2015 judgment in California against MacCord, his ex-wife, and one of his companies in the amount of $119,577 has been transferred to D.C. for collection. It remains uncollected to this day, according to the D.C. attorney who is handling the matter.

For Bowser and any D.C. official thinking of changing the law on behalf of MacCord and Digi Media, a pair of cases in Washington state are particularly instructive.

According to a lawsuit filed in 2010 in King County Superior Court, MacCord had controlled a company called Fourpoints Communications, which needed capital to manage outdoor advertising structures primarily on land controlled by Native American tribes. In November 2007, the lawsuit states, Fourpoints entered into a securities purchase agreement with New York investors who invested $5.5 million with the company and put up an additional $6.5 million in loans based on MacCord’s industry experience and representations of his “unique abilities.”

According to a sworn declaration by one of the investors, MacCord also was presenting opportunities to invest in wall signs in Seattle, Pennsylvania, and D.C., again based on his industry experience and a business plan two-and-a-half years in the making.

As CEO of Fourpoints, the lawsuit states, MacCord began transferring units in violation of an operating agreement, forging waivers of a prohibition of such transfers, misappropriating hundreds of thousands of dollars for personal use and misleading investors in “a pattern of self-dealing and outright fraud which completely undermined Fourpoints’ business and comprised the most severe betrayal of trust by a fiduciary.”

In November 2010, members of the board of Fourpoints’ holding company fired MacCord and removed him from the board, the lawsuit states.

MacCord told LL last week that Fourpoints simply sued him after its business went bust in a crashing economy, and that he settled the case in 2012 without admission of wrongdoing.

But a related case filed in U.S. District Court for the Western District of Washington by a different investor accused MacCord of securities fraud and involved allegations related to his business activities in D.C.

In the spring of 2009, the federal lawsuit states, MacCord began telling the investor about his billboard business. He claimed to have more than 20 years in the sign business in D.C., and with his Bentley and a “grandiose estate in Preston,” MacCord exuded success, the federal lawsuit states.

That June, while still CEO of Fourpoints, MacCord told the investor the company was valued at $40 million. Through Wall to Wall Advertising, a company he controlled, MacCord sold the investor $2 million in securities in Fourpoints, which he represented as a profitable firm that was free of local regulatory authority because it operated on Native American lands, the suit states. In reality, Fourpoints’ signs were not immune from local land use regulations, and were shut off due to public backlash, according to the suit. Yet MacCord continued to claim revenue growth even as Fourpoints was losing money and in debt, the lawsuit states, until it was forced to liquidate its assets at a loss.

After the investor learned of MacCord’s alleged misrepresentations in the King County case, and it became clear that Fourpoints was going under, MacCord et. al. began promising to make the investor whole through MacCord’s businesses in D.C.—namely, Digi.

“After a year, [the investor] delivered a draft complaint to Defendants and they responded by entering successive tolling agreements for nearly two years while they repeatedly tried to close transactions to make [the investor] whole. Like all their promises before, each of these transactions never materialized…”

The federal lawsuit eventually settled too. The investor’s lawyer, Chip Goss of Bellevue, Washington, says he cannot discuss terms of the settlement because it is under seal. He is careful not to disparage MacCord or any of his partners, associates, or companies. But he describes a trip to D.C. last year during which he and his client met with MacCord, Wilmot, and a pair of real estate investors who were excited about the prospects of Digi Media’s sign installation. “[MacCord] escorted us around town to where the signs would be installed, and we met with landlords who were excited about the concept,” Goss says. “The real estate component was that Digi identified a loophole in the law, and once they exploited it, landlords would be clamoring to be involved.”

Time was of the essence, Goss says. “There was a recognition in the business model that the loophole probably was not going to last,” he says. “At one point, [MacCord] proposed putting up 66 digital signs in one weekend in anticipation of the loophole closing.”

Another factor was the politics of the District of Columbia, Goss recalls. “They said that there was a substantial political operation that could deliver for them. My understanding is that the signs could be grandfathered if the city tried to shut them down. There was no question MacCord was running around town with political players, working the system.”

Asked whether he had any contact with government authorities, Goss says he received a subpoena from the Securities Exchange Commission about a year ago for documents in the Fourpoints case and some that didn’t make it into the court record. He received a follow up inquiry from the SEC but he does not know what became of it.

The SEC has shown interest in MacCord’s D.C.-based venture as well. LL got his hands on a subpoena “In the matter of Digi Outdoor Media” that was delivered to Eagle Bank in June. Bank president Ron Paul says Eagle was not an investor in the Digi venture, though it is possible the bank could’ve made a loan or issued a letter of commitment. He was unaware of the subpoena and unaware of the status of any investigation.

An SEC official from San Francisco says the agency doesn’t comment on matters that have not resulted in a formal report.

Bowser, Evans, Wilmot, and Perry have all declined to respond to LL’s calls. MacCord declined any further comment.

But it would be safe to say that with all MacCord has put into his D.C. digital sign venture, and all that D.C. has put him through, not to mention his personal and business history, investors might be getting nervous by now—even as Bowser breathes a sigh of relief.

Whether Evans and the D.C. Council are done with Digi is another story.