[UPDATE: Michael Cohen responded to McClatchy after the publication of this story to provide an explanation of who bought the properties. For more details, read here.]

Donald Trump’s long time business lawyer Michael Cohen may be best known for his aggressive campaign television defenses of the real estate mogul, his role in an abortive effort to build a Trump Tower in Moscow and allegations that he attended a meeting last summer with Russians in Europe.

But while serving as a top executive at the Trump Organization for a decade, Cohen himself was a sometime New York real estate wheeler dealer whose companies appear to have netted as much as $20 million in profit by flipping properties to mysterious buyers.

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The facts surrounding one of Cohen’s ventures in particular raised red flags for several experts interviewed by McClatchy.

In 2014, a mysterious buyer using a limited liability company that hid the purchaser’s identity paid $10 million in cash for a small apartment building on New York’s lower east side that Cohen had purchased just three years before for $2 million. The handsome appreciation came despite the fact that the assessed value of the property, at 172 Rivington St., hardly budged in these years, hovering around the price Cohen paid for it.

Three other properties Cohen bought and sold in roughly the same time frame followed a similar pattern. Each was purchased by a different LLC, but were tied together by the fact that a lawyer, Herbert Chaves, served as the LLCs’ manager.

“An all cash purchase by an LLC of an overvalued property in Manhattan is usually worth a closer look by federal investigators,” said Jaimie Nawaday, a former federal prosecutor and money laundering specialist who is now a partner with the New York law firm Kelley Drye & Warren. “There are perfectly good reasons to buy and sell through LLCs, but the combination of facts is one that tends to arouse interest.”

Cohen did not answer questions about the buyer’s identity or how the transaction was conducted. Herbert Chaves, a lawyer who served as “manager” for the LLC that paid $10 million for the property, declined comment.

Cohen, who is still one of the president’s private lawyers, has drawn increasing scrutiny in recent months from federal investigators – three congressional committees and Justice Department Special Counsel Robert Mueller – who are looking into Russian meddling in the 2016 elections and whether any Trump associates were tied to it. Mueller is also examining evidence of possible Russian money-laundering in the United States.

Cohen was interviewed Tuesday by House Intelligence Committee investigators. The Trump campaign’s digital honcho, Brad Parscale, was also questioned by the committee, a congressional staff member said.

Cohen will be questioned behind closed doors by the Senate Intelligence Committee this week, too. He was to appear at a public hearing of that panel Wednesday, but the session has been postponed.

The investigations have been digging into Cohen’s role in the abortive effort to build a Trump Tower in Moscow that occurred in late 2015 and early 2016 during the campaign, undercutting Trump’s statements about not having any business dealings with Russia. The probes are also looking at Cohen’s part earlier this year in working with a controversial Ukrainian legislator to push a short-lived, pro-Moscow “peace plan” between the two countries, an effort about which Cohen has offered conflicting accounts.

Cohen is also expected to face tough questions about allegations in a dossier compiled last year by an ex-British spy that he attended a secret meeting in Prague in late summer 2016 with some computer hackers and Russian operatives.

Cohen has vehemently denied that he was in Prague last summer or met with Russians. “The #Russian dossier is WRONG!” Cohen has tweeted.

Last month, Cohen told Senate investigators in a broad statement that “I emphatically state that I had nothing to do with any Russian involvement in our electoral process.”

Cohen did not respond to calls for comment or several emails from McClatchy with detailed queries. But he and his lawyer Stephen Ryan have said he is cooperating with the investigations.

Cohen’s real estate deals have until recently gotten less attention.

Besides his Rivington Street property, he acquired three other apartment buildings in the same time period, buying them for a total of about $9 million in late 2012. He sold them two years later for a total of over $20 million, even though their assessed value had hardly changed.

The purchaser in each case was a different LLC managed by Chaves, the man linked to the buyer of the Rivington Street building.

“[W]hat should raise red flags among money laundering experts are purchases way above the assessed value, combined with all cash purchases. These are potential fingerprints of money laundering,” said Louise Shelley, a professor at George Mason University and a specialist in money laundering, “But one needs to carefully investigate these patterns of behavior which, although they arouse suspicions, could be explained by market opportunities.”

And Cohen, a 51-year-old multimillionaire, has never been overcautious about seizing his opportunities. Among other businesses, Cohen has run a mid-sized New York taxi operation that used such colorful names as Sir Michael Hacking Corp. and Mad Dog Cab Corp. And Cohen also was a seven figure investor in 2003 in a floating casino in Florida that soon went bust, leaving in its wake a spate of lawsuits alleging that it stiffed many suppliers and employees.

In addition, Cohen served on the board of an ethanol company in Ukraine, where his wife was born. And the former personal injury lawyer has longtime ties to Felix Sater, the Russian-born operative with whom Cohen explored the Moscow Trump tower deal last year; Sater is a twice-convicted former government informant whose associates were accused of having mob connections.

McClatchy reported exclusively in late June that Cohen led failed efforts by the Trump Organization in 2011 to create Trump Diamond, a glass obelisk tower in Astana, the capital of Kazakhstan, which has been ruled by strongman Nursultan Nazerbayev since 1989.

This June, at a D.C. fundraiser for the Republican National Committee and his re-election campaign, Trump heaped praise on Cohen, who’s now a national deputy finance chair for the RNC, but hinted at the legal clouds hanging over Cohen. “Michael is a great lawyer, loyal, a wonderful person, talented, loves being on television,” said Trump, according to an audio recording first reported by the New York Times. “I miss you man.”

Cohen was arguably best known during the 2016 campaign for some testy interviews defending Trump. In one case, Cohen became agitated as an interviewer cited poor polling numbers for the candidate. In response, Cohen kept barking “says who?,” bolstering his notoriety as a pitbull for Trump.

Peter Stone is a McClatchy special correspondent