Arthur Engoron

Former President Donald Trump's business empire was dealt a severe blow by New York Judge Arthur Engoron on Friday, and one longtime Democratic strategist is arguing that the nine-figure judgment is a lasting stain on Trump's image as a savvy business magnate.

In a Saturday column for the Guardian, Sidney Blumenthal — who was a senior adviser to former President Bill Clinton — wrote that despite his father, Fred, trusting him with both his sizable real estate portfolio and the family's name, Trump has been "steering the family legacy on to the rocks."

Following the massive financial fraud penalty Judge Arthur Engoron assessed on Donald Trump on Friday, the former president will likely have to sell off some of his assets and, with the clocking ticking and interest on the potential $450 million owed piling up, possible buyers will have Trump over a barrel.

Speaking with MSNBC host Ali Velhsi on the Saturday morning after the Friday bombshell multi-million dollar financial fraud ruling, Donald Trump biographer Tim O'Brien stated the market for the former president's properties is already down in a post-Covid economy. Add to that, he noted, potential buyers know he badly needs the money.

Telling the MSNBC host Trump is "...going to have to sell some things," O'Brien explained what the former president will likely part with won't bring in what he hopes to get.

"If he sells urban skyscrapers in post-Covid cities where the occupancy rates are low, tenants have been fleeing and the values have been degraded because of it, it is going to be something of a fire sale," he explained to the host.

"You know, other developers are going to know he needs to sell, he won't get top price," he continued. "He's also always loathed to part with his toys and I think that's also going to be stressful."

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"I don't see him having any end-around," he added. "I don't think his appeal will be successful. I could be proven wrong, but Tish James, the New York State Attorney General, came at him under statutes -- they give the attorney general a lot of prosecutorial deference; the court system in New York has always respected that."

"And, again, as you noted in the tweet you showed at the top of our segment, he can't help himself but continue to go after the rule of law and try to degrade American's faith in a system of laws," he remarked. "The judges don't take kindly to that, prosecutors don't take kindly to that. It hurt him in court in the E. Jean Carroll case when he went after the judge. It hurt him in this court when he went after Engoron and he continues to do it to his own detriment."

Appearing on MSNBC on the morning after Donald Trump, his two sons and the Trump Organization were slammed by Judge Arthur Engoron with a financial fraud penalty that could exceed $450 million, one ex-prosecutor suggested the IRS and the DOJ could be waiting in the wings.

Speaking with host Ali Velshi, legal analyst Catherine Christian acknowledged that New York Attorney General Letitia James had indicated she would be passing on some of her findings that led to the former president's conviction to the Department of Justice.

She added that Trump and his sons, Donald Jr. and Eric may also be hearing from the IRS.

"What is the potential culpability beyond this trial? Is there something beyond this for Donald Trump?" host Velshi asked.

"If now the federal government, the Southern District of New York sort of passed on this publicly, but that does not mean that they can't, as long as it's within the statute of limitations take another look," she replied.

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"And clearly, the federal government, the Internal Revenue Service, they sort of never stop looking at you, and so yes, the AG's office referred to it to other authorities, and it could be possible that each of the defendants, not just Donald Trump, his sons, [Allen] Weisselberg could be in legal jeopardy, even criminal jeopardy."

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Trump's legal defeats tallying nearly $500 million may break the bank and they're certainly inspiring jokes.

On the day that Judge Arthur Engoron ruled that former President Donald Trump must pay $355 million for years of committing widespread fraud by inflating his assets to secure attractive loans and deals — some sought levity and manufactured slanted composites to mock his eponymous 58-story Midtown Manhattan Trump Tower.

Former President Donald Trump gave an enraged public speech from Florida on Friday night after his massive loss in the New York civil fraud case, accusing anyone and everyone who touched the case — and some people who didn't — of being corrupt and out to destroy his political and business career.

Judge Arthur Engoron found Trump liable for more than $355 million in the case, after Attorney General Letitia James presented her case that he and his two adult sons systematically manipulated the value of their properties, lied to investors, and defrauded the state tax agency and banks issuing them loans — all of which Trump denied yet again in his response.

Former President Donald Trump can't stop speaking his truth after Justice Arthur Engoron ordered him to pay more than $355 million in damages for civil fraud.

Not long after Trump posted an epic screed on Truth Social Friday, he returned to his social media site to repeat his grievances and bemoan his lot in New York City civil court.