Trump Organization CFO Allen Weisselberg reportedly still isn't cooperating with prosecutors.
Legal experts say as a prospective key witness, he may be holding out for the best possible deal.
Weisselberg also may never cooperate with the Manhattan DA's inquiry into the Trump Organization.
The Manhattan District Attorney's Office is still trying to secure the cooperation of the would-be star witness in its criminal investigation into the Trump Organization, according to The New York Times, and weighing whether to bring charges against Allen Weisselberg as soon as this summer.
For two years, the district attorney's office has been investigating whether the Trump Organization broke state laws by misrepresenting its financial information for tax, loan, and insurance benefits. Weisselberg, the chief financial officer of the company and the Trump family's personal bookkeeper, is also under criminal investigation as part of the effort, The Times reported.
Legal experts told Insider the chief financial officer may not be cooperating yet because he's holding out for prosecutors to offer him the best possible deal.
"He's holding out, maybe, because he's saying to himself, 'Listen, they need me, so I'm going to cut the best deal that I possibly can instead of taking their first offer out of the box,'" said Randy Zelin, a defense attorney at Wilk Auslander LLP and former New York state prosecutor.
Manhattan prosecutors have gone to great lengths to pressure Weisselberg into cooperating. They've subpoenaed his grandchildren's school and are investigating his son Barry, who also works at the Trump Organization and whose finances are comingled with the executive's, according to Jennifer Weisselberg, Barry's ex-wife.
Despite that pressure, Allen Weisselberg still hasn't flipped, according to The Times.
It's not clear whether Manhattan District Attorney Cyrus Vance Jr. will ultimately bring charges against Trump, Weisselberg, the Trump Organization, other company executives - or anyone at all.
As the keeper of the Trump Organization's and Trump family's finances, Weisselberg is best-situated to guide prosecutors through financial documentation to make or break a criminal case against Trump or his company. Weisselberg may be using that leverage to get the best deal possible for himself and for his family members, experts said.
Jeffrey Robbins, a former federal prosecutor who oversaw money-laundering investigations, told Insider that prosecutors may be seeking harsh penalties against Weisselberg to demonstrate the severity of the Trump Organization's conduct to a jury. Weisselberg may be fighting to ensure he doesn't go to prison, Robbins said.
"The prosecutors know that in a 'he said, he said' contest with the former president of the United States, it would be important for the key cooperating witness to serve time - so that the jury is more inclined to believe him," Robbins, now an attorney at Saul Ewing Arnstein & Lehr, told Insider. "They may be insisting that Weisselberg agree to serve time - and that may well be something that Weisselberg is unprepared to do."
There's a chance Weisselberg may not cooperate at all
Weisselberg may also simply not cooperate, calculating that he'd rather take his chances with the Trumps at the defense table.
It doesn't make much sense for him to cooperate with prosecutors - which will almost certainly mean pleading guilty to some charges himself - when there's a chance he could be acquitted. Weisselberg may believe that his loyalty to Trump will pay off and that he has the money to defend himself, Zelin said.
While Vance is widely expected to make a charging decision before his retirement at the end of the year - and has impaneled a special grand jury for the inquiry, according to ABC News - there's a possibility his successor may shy away from the case.
The incoming Manhattan DA may decide that the Trump investigation is too expensive and that New Yorkers would prefer to spend resources on street crime and shootings, which the New York Police Department says are increasing. If Weisselberg were to cooperate and plead guilty only to have Vance's successor drop the case, Zelin said, he would have lost Trump's good graces for nothing.
"Now, for Allen Weisselberg, the music is stopped and there were no chairs for him to sit at," Zelin said. "I'm sure he's saying to himself, 'Maybe that could happen, and if I just hold out, maybe this case goes nowhere.'"
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