Donald Trump hasn't had the easiest month, with both the FBI search of his Mar-a-Lago residence and a New York deposition to contend with.

The hearing in New York centers on Trump's tax affairs and valuations of Trump organization assets.

Reports of the hearing said that Trump pleaded the Fifth amendment more than 440 times.

Trump, in a statement, said: "I once asked, 'If you're innocent, why are you taking the Fifth Amendment?' Now I know the answer to that question."

"When your family, your company and all the people in your orbit have become the targets of an unfounded, politically motivated Witch Hunt supported by lawyers, prosecutors and the Fake News Media, you have no choice," Trump said.

"Accordingly, under the advice of my counsel and for all of the above reasons, I declined to answer the questions under the rights and privileges afforded to every citizen under the United States Constitution," he added.

However, the circumstances of why Trump chose to use the Fifth are more complex than a simple "no comment" statement in a criminal matter.

To find out what it all means, Newsweek investigated Trump's past comments about the amendment, his potential reasoning for the apparent U-turn, and what it could mean for future hearings.

Trump is being rather coy in his statement, implying that in his past comments he merely questioned the reasons for taking the fifth. In fact, he openly criticized Hillary Clinton's aides during the 2016 presidential campaign for pleading the Fifth in the probe of her use of a private email server.

"So there are five people taking the Fifth Amendment, like you see on the mob, right? You see the mob takes the Fifth. If you're innocent, why are you taking the Fifth Amendment?" Trump asked the crowd rhetorically at an Iowa rally in September 2016.

Even though Trump made the admission that his previous comments may have been unwise, critics on social media were quick to point out the apparent hypocrisy.

There are a few things to unpack here. Firstly, Trump made a false equivocation comparing the Hillary Clinton email probe alongside "the mob." Although the investigation was led by the FBI, it examined whether criminal charges could be sought.

The comparison with the mob did imply, arguably, that Clinton was under criminal investigation.

On July 5, 2016, then-FBI director James Comey released a statement saying that the FBI "cannot find a case that would support bringing criminal charges on these facts" adding "we are expressing to Justice our view that no charges are appropriate in this case."

That being said, the comments on Twitter about Trump's use of the Fifth in New York do not make distinctions about the nature of the hearing either.

The civil case, led by New York District Attorney Letitia James, is investigating the valuation of Trump's assets, and whether the former president's business, the Trump Organization, misrepresented the stated valuations of some of its real estate assets for financial gain, including better terms on loans and insurance, as well as tax benefits.

Trump has strongly denied any wrongdoing.

Although the principle of the Fifth amendment remains the same whether in a criminal or civil case, the reasons for doing so are more nuanced, something that was not explained by Trump's social media critics.

To assess this in more detail, Newsweek spoke to a number of legal experts in constitutional law and criminal and civil litigation to find out more.

Professor Erwin Chemerinsky, Dean of Berkeley Law, told Newsweek: "A person has a right not to answer any questions, in a criminal or civil case, that might lead to statements that could lead to criminal liability.

"In a criminal case, no adverse inference can be drawn from invoking the privilege against self-incrimination," he added.

"In a civil case, an adverse inference can be drawn from invoking the privilege."

Adverse inference is a legal term, which effectively means that when plaintiffs try to present evidence on a point essential to their case, and cannot do so because the document has been destroyed by the defendant, the jury can infer that the evidence would have been adverse to the defendant, and adopt the plaintiff's reasonable interpretation of what the document would have said.

This was supported by Professor Katherine J Florey of UC Davis School of Law, who said that the consequences of taking the Fifth can have a more negative effect on the outcome of a civil case.

"In the criminal setting, juries are not permitted to draw an adverse inference from a defendant's decision to invoke the Fifth, but in some circumstances they may be permitted to do so in civil trials," Professor Florey said.

"It is also the case that, when a defendant in a civil trial relies on the Fifth, they will generally be barred from offering other evidence and/or testimony on the issue about which they refused to answer questions. The idea is to prevent defendants from selectively disclosing only information that helps them.

"In short, relying on the Fifth in a civil proceeding may have some negative effects in that proceeding, allowing an adverse inference and preventing the defendant from introducing some potentially helpful evidence.

"On the other hand, it may be the right choice for a defendant who has significant concerns that they may be criminally prosecuted."

So, while pleading the Fifth in the deposition could prevent Trump from providing other evidence at a later point, which could support his case, the prospect of criminal liability may be looming large.

Jimmy Gurule, a Professor of Law at the University of Notre Dame, added that anything Trump said during his deposition "could be used against him in a criminal trial on charges related to allegations that he unlawfully inflated the value of his real estate properties in NYC."

"If proven, Trump could be charged and convicted of tax fraud, as well as wire fraud and mail fraud," Professor Gurule said.

"Second, Trump fears that disclosing harmful information during his deposition could be used against him to prove the civil claims. For example, his deposition testimony could be used to prove that he 'knowingly' inflated the value of his real estate holdings to avoid paying taxes.

"Finally, Trump likely fears that if he testified untruthfully during his deposition, he could open himself up to perjury charges."

The possibility that his tax affairs may be exposed, or that Trump could end up saying something untruthful, may have given him enough reason to remain silent during the deposition.

Details of the hearing on Wednesday, August 10, 2022 haven't been revealed.

It's been reported that Trump pleaded the Fifth amendment more than 440 times, according to an NBC News source, who claimed to have knowledge of the deposition. Newsweek has not been able to independently verify this.

Trump's attorney Ron Feschetti said that the only question he answered was his name. A spokesman for Letitia James' office, confirmed the former president took the Fifth.

"Attorney General Letitia James took part in the deposition during which Mr. Trump invoked his Fifth Amendment right against self-incrimination," James' statement said.

"Attorney General James will pursue the facts and the law wherever they may lead. Our investigation continues."

Some commentators also speculated that James could expand her probe to bring criminal charges from a different Trump case, led by Manhattan District Attorney Alvin Bragg, who in the end decided not to indict the former president. While that remains a possibility, there is so far no evidence that she will do so.

Finally, as much as we can speculate on Trump's motivation for pleading the Fifth, that too is an unknown.

Trump has been openly hostile toward Attorney General James and believes the probe is politically motivated, that is part of a broader "witch hunt" targeting him and his allies.

Newsweek has contacted Donald Trump for comment.

Correction 08/12/22 10.53 a.m. ET: A spelling of Hillary Clinton's first name was corrected

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Why Did Trump Plead The Fifth Amendment?What We Do Know ... - Newsweek