Allen Weisselberg, the former chief financial officer of the Trump Organization, was recently released from New York's infamous Rikers Island prison after serving time on tax fraud charges that he pled guilty to last year under pressure from the Manhattan District Attorney's Office.

Weisselberg could soon be headed right back to prison, however, as District Attorney Alvin Bragg is now threatening to charge him with perjury and insurance fraud, according to Politico's Playbook on Friday.

Those threats from Bragg are part of a transparent attempt to compel Weisselberg to flip on his old boss, former President Donald Trump, and testify against him on other alleged criminal matters.

Under pressure to flip on Trump

According to Newsmax, Weisselberg was sent to Rikers Island on a five-month sentence in January but was granted early release after 100 days for good behavior and was just recently set free from the notorious prison.

He had pleaded guilty to allegations of tax fraud that had been pressed against him after he had steadfastly refused prior concerted attempts by prosecutors to deliver information that would support criminal charges against his former boss of nearly 50 years, Trump.

Unfortunately for him, and despite the fact that he was already prosecuted and imprisoned for, in effect, refusing to cooperate with a targeted prosecutorial campaign against Trump, Weisselberg will once again face the threat of imprisonment if he continues to stand in defense of his personal friend and former employer.

Perjury and insurance fraud charges

The New York Times was the first to report on Friday that Manhattan DA Bragg had set his sights once again on Weisselberg, 75, as a potential key witness against former President Trump.

Bragg is said to be considering a perjury charge against Weisselberg in relation to sworn testimony he gave to Democratic New York Attorney General Letitia James in 2020 as part of her own long-running investigations into the Trump Organization and the former president himself.

The Times noted that it was unknown what Weisselberg is alleged to have perjured himself about in that 2020 interview, nor was it clear how Bragg would be able to prove that Weisselberg had lied to the state attorney general -- not to mention why AG James hadn't already pursued such a charge if he did, in fact, lie under oath to her office.

In addition to the perjury charge, the outlet further reported that Bragg is also weighing the possibility of pressing separate insurance fraud charges against Weisselberg that would be in relation to allegations that the Trump Organization manipulated the largely subjective appraised value of certain properties.

That said, The Times pointed out that there was "no indication" that Weisselberg would be any more likely to flip on Trump under a renewed pressure campaign than he was before, or that criminal charges were even imminent.

Further, Bragg is likely to face some criticism over his threats to imprison a 75-year-old man who has already been prosecuted and served time for refusing to buckle under prior threats.

If charged, would face same judge overseeing Trump "hush-money" case

The Times reported that if DA Bragg does decide to file criminal charges against Weisselberg, the former Trump Organization executive would likely end up in the courtroom of Judge Juan Merchan, who has presided over previous trials involving the business and is the one who sentenced Weisselberg to 100 days in Rikers Island and also "warned him that he typically imposes tougher sentences in white-collar cases."

Merchan, of course, is also the judge who is presiding over Bragg's prosecution of Trump over alleged criminality with regard to "hush-money" payments he made in 2016 to two women to buy their silence about alleged prior affairs.