Trump’s Sideshow Characters Keep Racking up Huge Legal Bills

It’s not just Donald Trump who keeps losing his legal battles.One by one, the former president’s associates are getting shot down in court and being ordered to pay up for their misbehavior.The latest is the former Trump adviser and current government-hating podcaster Steve Bannon. He was convicted for ignoring a congressional subpoena to testify about

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It’s not just Donald Trump who keeps losing his legal battles.

One by one, the former president’s associates are getting shot down in court and being ordered to pay up for their misbehavior.

The latest is the former Trump adviser and current government-hating podcaster Steve Bannon. He was convicted for ignoring a congressional subpoena to testify about his role in Trump’s Jan. 6 insurrection. Bannon never did testify, and then he stiffed his lawyer for years of research and courtroom work.

The same lawyer who helped Bannon land a Trump presidential pardon that spared him a conviction for defrauding nonprofit donors eventually took him to court over unpaid legal bills. And last week, a New York judge ordered Bannon to pay up the missing $480,000, brushing aside his excuses—namely, that the attorney, Bob Costello, did bad lawyering without permission.

But Bannon’s hole is on track to get even deeper, now that the attorney at Costello’s firm who had to claw back those missing dollars says he’s now owed money for his time as well. Joseph N. Polito, a professional colleague of Costello’s, has filed an itemized hourly bill that shows his firm spent $66,896 on the five-month case—including settlement talks that went nowhere.

If that’s approved by Justice Arlene Bluth, Bannon’s bill will break the half-million dollar mark.

Then there’s Rudy Giuliani, the former New York City mayor who became Trump’s personal lawyer and led efforts to overturn the 2020 election, committing professional suicide in the process. Aside from battling to keep his law license, Giuliani is also fighting off a defamation lawsuit by Ruby Freeman and her daughter Shaye Moss—the Georgia poll workers whom Giuliani falsely accused of taking part in a vast conspiracy to sneak suitcases of fake ballots to tank Trump’s re-election bid.

Last Thursday, just as Bannon got hit with an even bigger legal bill, a federal judge in the nation’s capital ordered Giuliani to immediately shell out $89,172 for failing to turn over evidence in the defamation case. Giuliani should have paid it by July 7, but he blew that deadline and now has until next Tuesday, or he could face additional sanctions.

Giuliani’s admonishment came from none other than U.S. District Judge Beryl A. Howell, the very same judge who until recently oversaw secretive disputes stemming from a District of Columbia grand jury’s criminal investigation of the former president.

Howell was the judge who kept pressuring Trump’s legal team during the Department of Justice’s investigation into missing classified documents that Trump was hoarding at the former president’s Mar-a-Lago estate. On her last day as the district’s chief judge, she controversially turned over a Trump lawyer’s notes directly to Department of Justice Special Counsel Jack Smith.

Now that she’s back to being a regular federal judge, Howell is keeping the pressure up on Giuliani.

In her latest order, she ripped into the experienced lawyer—who once had the most coveted legal job in the country as Manhattan federal prosecutor—for improperly responding in court documents. She noted that Giuliani recently pushed back on efforts to make him turn over more evidence, but he didn’t bother to do the same on behalf of his two businesses in question, Giuliani Partners and Giuliani Communications.

“He has no one to blame but himself for ignoring plaintiffs’ pending motion to compel the Giuliani businesses to comply with discovery obligations,” Howell wrote in a searing tone, giving him a week to respond and little extra time to turn over more evidence.

Giuliani has also been put on notice that hellfire is headed his way if he doesn’t get his affairs in order.

“Defendant Giuliani is CAUTIONED that failure to comply… may result in severe discovery sanctions,” Howell wrote, warning that she might punish him with sanctions, more legal fees, and even close the case by ruling against him entirely.

But that’s not all. Last Thursday, Howell also put another Trump associate on notice: Bernie Kerik.

The disgraced former New York Police Department commissioner, who also took part in efforts to discredit the Georgia poll workers as an investigator for Giuliani, has so far refused to turn over evidence and answer certain questions while in a deposition with the women’s lawyers. Kerik has until next week to list each document he hasn’t turned over yet, lay out why he hasn’t, and explain why he shouldn’t get hit with a legal bill just like Giuliani’s.

Howell said she would give Kerik’s lawyer, Timothy Parlatore, “a final opportunity” to comply and turn over evidence, taking a jab at him with a snarky remark.

Howell wrote that she was “giving Parlatore the benefit of the doubt that his declaration reflected merely a misunderstanding of the applicable law rather than an effort to delay.”

However, Parlatore has relied on the same argument he made to the House Jan. 6 Committee that wanted a similar batch of records and didn’t get them: Some documents are protected by attorney-client privilege that belongs to Trump’s re-election campaign.

Importantly, Kerik’s problems could disappear in an instant—if Trump decides to waive that privilege.

While these three MAGAworld associates have been getting slapped around in court, another Trump lawyer—Alina Habba—has been trying to escape a nearly $1 million bill she accrued herself by filing a spurious lawsuit against political foes.

This one dates back to Trump’s conspiracy-laden revenge lawsuit against Hillary Clinton and others who participated in efforts to link Trump to Russian efforts to meddle in the 2016 election.

Former New York City Mayor Rudy Giuliani, an attorney for former U.S. President Donald Trump during challenges to the 2src2src election results, exits U.S. District Court after attending a hearing in a defamation suit related to the 2src2src election results


REUTERS/Leah Millis/File Photo

In January. U.S. District Judge Donald M. Middlebrooks in South Florida shut that lawsuit down with a scathing order, citing how “a continuing pattern of misuse of the courts by Mr. Trump and his lawyers undermines the rule of law, portrays judges as partisans, and diverts resources from those who have suffered actual legal harm.”

“This case should never have been brought. Its inadequacy as a legal claim was evident from the start. No reasonable lawyer would have filed it,” he said, scolding Trump and Habba before fining them $937,989.

But last week, Trump managed to convince the federal appellate judges in that circuit that the May release of the Durham report shed new light that somehow backed up his vindictive lawsuit about a supposed Clinton-led, deep-state conspiracy. A three-judge panel in Atlanta kicked the case back to Judge Middlebrooks.

Middlebrooks, who previously lectured Trump’s legal team for trying to judge-shop their Russiagate lawsuit to a Trump-appointed judge and already spent 46 pages ripping into them over their political vendetta, is poised to come down hard again.

DOJ Special Counsel John Durham’s four-year, $6.5 million law enforcement effort just rehashed what the DOJ inspector general found back in 2019—that there was no “deep-state conspiracy” and that FBI special agents properly opened “Crossfire Hurricane,” the Russia probe.

Last time, Middlebrooks and his staff listed the 47 lawyers and paralegals who were owed money for wasting time on this case. It might not be long before he updates those numbers again.

Of course, all these legal troubles pale in comparison to Trump.

The former president will be on trial in October, when he will try to save himself and his business from financial ruin from the New York Attorney General. (The New York AG has accused the Trumps of bank and insurance fraud in a gargantuan civil lawsuit.)

Then there are the legal troubles that could land the former president in prison. The Manhattan District Attorney will put Trump on trial in March for faking business records when he tried to cover-up a hush payment he made to the porn star Stormy Daniels in an attempt to keep her from going public and ruining his ultimately successful presidential campaign in 2016.

And at some point, Trump will be on trial in South Florida against the Department of Justice to defend the way he hoarded classified documents after leaving the White House—and for trying to cover up the whole mess.

Trump is also bracing for yet another criminal indictment from DOJ Special Counsel Jack Smith, who is investigating the way Trump resorted to filing nonsense lawsuits, intimidating state elections officials, and even recruiting fake electors to stay in power after losing the 2020 election.

And that’s on top of Georgia. In the next few weeks, an Atlanta grand jury is expected to indict him for threatening Georgia’s secretary of state to “find 11,780” votes to flip the election there.

While his associates are guarding their wallets, Trump is fighting for his life.

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