Allen Weisselberg’s History of Playing Dumb Probably Won’t Save Him (or Trump) This Time

Back in July, the Manhattan District Attorney’s investigation into Donald Trump and his company took a major step forward when the Trump Organization and its longtime CFO, Allen Weisselberg, were charged with more than a dozen crimes. Accused of running a 15-year scheme to help executives like Weisselberg evade taxes by compensating them with “fringe benefits” like apartments, cars, and private school tuition that were kept off the books (but recorded in an internal spreadsheet!), the charges included conspiracy, grand larceny, and multiple counts of tax fraud and falsifying records. Both the Trump Organization and Weisselberg have pleaded not guilty and, to date, have suggested they’ll fight the allegations at trial. Presumably, though, the senior executive, who has previously described himself as Trump’s “eyes and ears” at the company, has at least spent some time considering changing his plea and cooperating against the ex-president.

For one thing, he faces up to 15 years in prison, and at the current age of 74, that’s quite a long time. For another, prosecutors allegedly have evidence that his son, Barry Weisselberg, who has not been accused of wrongdoing, also dodged taxes with the help of the Trump Organization, and one would think Weisselberg the Elder would sooner save his own kid than his boss. Oh, and for yet another, very few people believe he’s innocent. “If the allegations in the indictment are true, this was pants-on-fire tax evasion,” University of Chicago tax-law professor Daniel Hemel opined after the indictment was unsealed. “It is very hard to believe that this could have happened without the man on top knowing.”

Of course, people have done much stupider things in service to Donald Trump than gambling away their own freedom. (For example, coming extremely close to overthrowing democracy on his behalf). And while this is the first time he’s been criminally charged, and the stakes have never been higher, Weisselberg has previously been confronted with evidence of illegal activity on the part of the Trump Organization, and had to decide how to respond. And according to a new report from the Daily Beast, the CFO deployed a similar tactic in each situation: to just play dumb:

When Donald Trump’s charity was caught making an illegal political donation years ago, his longtime right-hand finance man, Allen Weisselberg, signed a letter to law enforcement that chalked it up as a mere mistake. In reality, as the Daily Beast recently revealed, employees were well aware that the money was going to a Florida politician.

When the Trump Foundation made its annual tax filings with New York state that incorrectly listed that donation—making it seem like it was going to a legitimate nonprofit—Weisselberg signed off on the document, he said, without actually reviewing it. By scribbling his signature with a thin black pen, he affirmed that he’d “reviewed this report” to make sure it was “true, correct, and complete.” As Weisselberg would later say, the truth was he hadn’t even read it. “I may have just glanced through it,” he told investigators during a sworn interview in October 2017. In fact, Weisselberg claimed to not even realize he was one of only three board members of the multimillion-dollar charity for 15 years. “I’m not a director,” he swore. “I’m just a treasurer.”

Such is the standard operating procedure of the now-indicted chief financial officer of the Trump Organization. Although his current legal strategy in his tax fraud case has yet to be revealed—with his lawyers merely describing the prosecution as “flawed”—this past behavior shows that his primary defense has basically been gross negligence. A disregard for oversight. Carelessness. Incompetence.

Yet while the “gee shucks, I’m just a country chief financial officer new to the big city” schtick might have worked in the past, it’s not clear he’ll be able to rely on it again. For starters, as his former colleague Michael Cohen has put it, the idea that Weisselberg isn’t keenly aware of every nickel that goes in and out of the Trump Organization is bullshit. “Allen Weisselberg [knows] every single dollar in, and every single dollar—not even dollar, to the penny. Every single penny in and every penny out [goes] through Allen Weisselberg’s desk, and then [is] reported, before and after, to Donald J. Trump,” Cohen said in May. That sentiment is backed up by his former daughter-in-law (and Barry’s ex-wife), Jennifer Weisselberg, who told the Daily Beast, of Weisselberg’s bumbling accountant routine: “He’s a liar. Allen is controlling. He has to know where every dollar goes. He can’t handle not overseeing every dollar. And he’s not going to sign something unless he knows what it says. He knows exactly what’s going on. He doesn’t want any loose ends.”

And then, again, there’s the idea that any of the criminal activity laid out by prosecutors could have gone down without Weisselberg’s knowledge, which legal experts say there is not. “I am optimistic he’ll be convicted. The law is fairly clear on what is income & what is taxable,” former U.S. attorney Preet Bharara remarked after Weisselberg was charged. “He’s a sophisticated executive; mistake is implausible. The company booked much of it as income. And juries hate rich tax cheats.”

Also not to be discounted is the fact that, according to the Manhattan D.A.’s office, Weisselberg literally kept spreadsheets of his and the Trump Organization’s crimes. As the indictment helpfully points out:

For certain years, the Trump Organization maintained internal spreadsheets that tracked the amounts it paid for Weisselberg’s rent, utility, and garage expenses. Simultaneously, the Trump Organization reduced the amount of direct compensation that Weisselberg received in the form of checks or direct deposits to account for the indirect compensation that he received in the form of payments of rent, utility bills, and garage expenses. The indirect compensation was not included on Weisselberg’s W-2 forms or otherwise reported to federal, state, or local tax authorities, and no income taxes were withheld by the corporate defendants in connection with the indirect compensation.

So yeah, the idea that Weisselberg will be able to just play dumb on this one seems slightly to extremely implausible, likely upping the chances he’s at least entertaining the idea of telling prosecutors everything he knows re: Trump. As former federal prosecutor Cynthia Alksne told MSNBC shortly after the charges were unveiled, “I think he will be a very hated defendant, Mr. Weisselberg, and I’m sure his defense attorneys have told him so.”

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