Or so prosecutors believe. The Manhattan DA’s office has tried to pressure Weisselberg into flipping on Trump for the past two years. His continued presence in Trump Tower is either a testament to Weisselberg’s loyalty, a testament to Trump’s innocence, or a testament to the science of wearing wires.

The Washington Post picks Door Number One:

Every day that Weisselberg arrives for work at Trump Tower — as he did that day, steering in from his Upper West Side apartment across town — could be seen as a public signal that he is sticking with Trump and deflecting investigators’ advances.

As the most senior non-Trump executive at the former president’s private, closely held company, Weisselberg is probably a key figure in prosecutors’ efforts to indict Trump, legal experts say. His central role in nearly every aspect of Trump’s business, revealed in depositions and news interviews over the past three decades, afforded him what former employees say is a singular view of the Trump Organization’s tax liabilities and finances. …

More than two years after opening an inquiry of the Trump Organization, Manhattan District Attorney Cyrus R. Vance Jr. has convened the grand jury that is expected to decide whether to indict the former president, according to two people familiar with the development, and is pressing Weisselberg to provide evidence implicating Trump.

Yet officials involved in the Weisselberg investigation have grown frustrated about what they view as a lack of cooperation from Weisselberg and believe he continues to regularly speak with Trump, according to a person familiar with the inquiry.

And why not? Weisselberg has a long track record of frustrating prosecutors who took aim at his boss:

Weisselberg handled the finances for Trump’s charitable foundation, which admitted to self-dealing and dissolved in 2018 after coming under investigation by the New York attorney general, according to a deposition he gave in 2017. He oversaw spending decisions at Trump University, the online program that drew three lawsuits before the settlement, according to his deposition in one of those cases. He signed checks to former Trump lawyer Michael Cohen that Cohen says were reimbursements for illegal payments Cohen made to Stormy Daniels and Karen McDougal to prevent them from publicly alleging they had affairs with Trump.

It’s true that Weisselberg cooperated in the Cohen probe after prosecutors gave him immunity. That didn’t work out completely to plan, though. Weisselberg’s involvement in that case had an ironic ending, which the Post notes parenthetically:

(He received immunity in a federal case against Cohen. Cohen later pleaded guilty to eight criminal counts and received a three-year sentence.)

In other words, Weisselberg doesn’t frighten easily. He’s played this game with prosecutors for long enough to know how to step through legal landmines. In none of these cases did prosecutors ever indict either Trump or Weisselberg.

This time around, however, prosecutors might have a little more leverage. The New York Times reported last week that a criminal indictment against Weisselberg would soon be forthcoming over criminal tax evasion, the kind of charges that could put Weisselberg at Club Fed for a few years. His former daughter-in-law has already been known to be cooperating with prosecutors on this issue, which DA’s office hoped would change all of Weisselberg’s calculations:

The Manhattan district attorney’s office appears to have entered the final stages of a criminal tax investigation into Donald J. Trump’s long-serving chief financial officer, Allen H. Weisselberg, setting up the possibility he could face charges this summer, according to people with knowledge of the matter.

In recent weeks, a grand jury has been hearing evidence about Mr. Weisselberg, who is facing intense scrutiny from prosecutors as they seek his cooperation with a broader investigation into Mr. Trump and the Trump Organization, the people with knowledge of the matter said. The prosecutors have obtained Mr. Weisselberg’s personal tax returns, the people said, providing the fullest picture yet of his finances.

Even as the investigation has heated up, it remains unclear whether the prosecutors will seek an indictment of Mr. Weisselberg, which would mark the first criminal charges stemming from the long-running financial fraud investigation into Mr. Trump and his family company.

The investigation into Mr. Weisselberg focuses partly on whether he failed to pay taxes on valuable benefits that Mr. Trump provided him and his family over the years, including apartments and leased cars as well as tens of thousands of dollars in private school tuition for at least one of his grandchildren. In general, those types of benefits are taxable, although there are some exceptions, and the rules can be murky.

That’s been on the table for months, though, and Weisselberg hasn’t budged. Maybe he’s playing hard to get with prosecutors, hoping to escape scot-free. Or perhaps Weisselberg has a good defense to those charges; he certainly can afford the best tax and criminal defense attorneys to represent him in a case as “murky” as this.

And it’s also possible that Weisselberg and prosecutors don’t have a case on Trump, even if Weisselberg’s inclined to cooperate. Trump is presumed innocent until proven guilty, and despite decades filled with various investigations, Trump hasn’t ever been indicted, let alone tried. They never got Weisselberg to flip before, of course, but it’s possible that Weisselberg has nothing significant to trade.

This looks more like a story about Cyrus Vance running out of time than it does of Weisselberg’s doom. Vance’s retirement means that the clock is winding down, and the frustration felt by prosecutors over Weisselberg’s refusals likely has more to do with the lack of any effective case against Trump and unsure leverage over Weisselberg. That may change if an indictment drops on the CFO this summer, but you can bet that Weisselberg has his legal campaign ready to launch.