Michael Cohen, President Donald Trump's former lawyer and confidant, walks...

Michael Cohen, President Donald Trump's former lawyer and confidant, walks out of federal court in Manhattan in April. Credit: Getty Images / Spencer Platt

About two months before Election Day in 2016, Donald Trump and his then-lawyer Michael Cohen were chatting about how to persuade a former Playboy model, Karen McDougal, to keep quiet about what she described as a long-term affair with the presidential candidate.

“We’ll have to pay,” Cohen said, according to a recording of the conversation that CNN broadcast Tuesday night.

“Pay with cash,” Trump appears to respond.

“No, no, no, no, no” Cohen says. Earlier in the conversation, Cohen suggested that he “open up a company for the transfer of all of that info” to the National Enquirer and its parent company, American Media Inc. AMI’s chairman, David Pecker, is a friend of Trump and he is also referred to on the tape. The Enquirer had purchased McDougal’s account of the alleged affair and never published it. Trump and Cohen appear to be discussing a second payment to McDougal (and there is no indication that it was ever made).

“I’ve spoken to Allen Weisselberg about how to set the whole thing up . . . ,” Cohen tells Trump. “So, I’m all over that.”

Weisselberg’s emergence on the Cohen-Trump recording should worry the president. Weisselberg, the chief financial officer of the Trump Organization, has detailed information about its business deals and finances. If he winds up in investigators’ crosshairs, he could potentially provide much more damaging information to prosecutors about Trump’s deal making than Cohen ever could.

Cohen reportedly is being investigated by federal prosecutors for possibly engaging in bank fraud, wire fraud and campaign finance violations. To the extent that his legal travails spill over onto Trump, it’s worrisome to the White House. But campaign finance violations aren’t likely to be as threatening to Trump as other more serious transgressions, such as, for example, obstruction of justice or exchanging policy favors for financial gain.

Moreover, Cohen has worked for Trump only since 2006, and he never operated as a traditional lawyer. Instead, he brought potential licensing deals to Trump’s attention for years and also worked with the career criminal and Trump business partner Felix Sater on a proposal for a Trump project in Moscow.

The news media and others have sometimes characterized Cohen as the man who knows all of Trump’s secrets or even, errantly, as someone who ran the Trump Organization with the president’s children. Not so.

Weisselberg, on the other hand, has worked for the Trump family since the 1970s, and knows more about the Trump Organization’s history and finances than nearly anyone. Almost 71, he joined the company after graduating from college. Now the CFO, he is one of the president’s closest business confidants. Weisselberg also was treasurer of the president’s troubled philanthropy, The Donald J. Trump Foundation, which the New York State attorney general has sued, claiming the foundation engaged in self-dealing. Weisselberg hasn’t been charged with any wrongdoing.

Over the years, Weisselberg’s professional duties came to include handling Trump’s personal finances as well as the Trump Organization’s corporate finances. He has paid household bills, made large purchases for Trump, and has communicated with Trump’s outside investment advisers. After Trump became president, his lawyers created a trust that safeguards his interest in the Trump Organization. The trust is run by Weisselberg and the president’s two eldest sons.

Unlike the Trump family, Weisselberg has remained out of the spotlight, quietly tending to Trump Organization operations. Now that he has surfaced in one of the most high-profile political and business investigations in the United States, that may be about to change.

Timothy L. O’Brien is the executive editor of Bloomberg Opinion.

Newsday LogoYour Island. Your Community. Your News.Digital AccessOnly 25¢for 5 months