Former President Donald Trump and New York Attorney General Letitia James are fighting a big, wordy war over a relatively small prize: a $110,000 check he sent her office in May.

The money, which sits frozen, for now, in an attorney general escrow account, is Trump's contempt-of-court penalty for flouting James' subpoenas last year, as she readied her massive September fraud lawsuit against the Trump Organization.

Trump, by Forbes' reckoning, is worth $3.2 billion. But he's sparing no effort to get his $110,000 penalty check back.

He wants it back so badly that his lawyers have filed a total of 977 pages of appellate paperwork seeking its return and the expungement of the original contempt order.

The fine was "vindictive," "speculative," "improper," "punitive," "excessive," and based on "threadbare justification," attorney Alina Habba argues over the course of a 233-page Notice of Motion, a 247-page Record on Appeal, and a pair of briefs totaling 497 pages.

"I don't think they're being strategic," said Tristan Snell, the lead prosecutor on the New York attorney general's investigation into Trump University, which settled for $25 million in 2016.

"I think this is being driven by animosity, pure and simple," said Snell, who now runs MainStreet.law, a firm focused on helping small and medium-sized businesses. 

Much of that animosity has played out in public. Trump has repeatedly called James "racist" and, perplexingly, "Letitia 'Peekaboo' James."

A lawyer for the attorney general's office, meanwhile, kept his response to Trump's appeal down to an also fervent, but far trimmer, 66 pages.

The response included a section of argument titled, "Mr. Trump's Contumacious Conduct Was Calculated to Impede OAG's Fraud Investigation."  "OAG" is short for Office of the Attorney General.

A state appellate panel of five judges began weighing Trump's contempt-order appeal Wednesday, as first reported by Bloomberg. Appeals typically take four to six weeks to decide.

The contempt-of-court order now under the panel's review had been issued back in April, by New York State Supreme Court Arthur Engoron, who, like the appellate panel, sits in Manhattan.

Engoron, "chose to blindly 'rubber stamp' the exact amount of daily sanctions requested" by the attorney general, Habba complains in her most recent filing in the appeal,  a 237-page brief from December.

Engoron is the same judge who in November imposed an independent monitor over the Trump Organization, in response to what he called Trump and his company's "demonstrated propensity to engage in persistent fraud."  Trump "Truthed" in response that Engoron is a "Radical Left Lunatic Judge in New York City."

Engoron is also the same judge presiding over the attorney general's fraud lawsuit, which accuses Trump, his company, and his three eldest children of a decade-long pattern of lying about the worth of company assets in financial documents.

The sweeping case seeks to permanently ban the Trumps from doing business in New York and is scheduled for trial in October.

Engoron has refereed fights between the attorney general and Trump's lawyers since the summer of 2020, when the AG first sought help getting the former president to comply with her investigatory subpoenas in the lead-up to the fraud lawsuit.

The appeal centers one of those fights, over James' contention that despite running an international real-estate and golf-resort business for decades, Trump only ever turned over 10 personal business documents to her investigation. Those few documents included such non-evidentiary curios as a photo of a grocery store, and several old news clippings about golf stars from the 1960s and 1970s.

The Trump Organization itself turned over 900,000 documents to the attorney general's probe — some 6 million pages. Still missing, though, the attorney general has alleged, were additional files from the paperwork trove they believed Trump stored in two dozen metal file cabinets on the 26th floor of Trump Tower in Manhattan.

"The Court should put an end to Mr. Trump's intransigence and subterfuge," James said in demanding Trump be fined $10,000 a day until he turns over all Trump Organization business documents in his personal custody, or else explain why he's empty-handed.

The judge agreed, telling the parties during a hearing, of Trump, "He can't produce what he doesn't have. But you can't just say, 'I don't have anything. You have to say where you looked." 

Engoron lifted the costly contempt-of-court order in June, halting the fine at $110,000, but only after Trump's lawyers turned over a set of affidavits swearing that there had been a thorough search, and indeed, Trump had nothing else to turn over. 

Trump's $110,000 remains in escrow until the appeal is decided. Habba and a spokesperson for James did not respond to requests for comment.

There's no small irony in Trump spending 1,000 pages to fight being in contempt for turning over too few pages.

Trump's extensive effort in an appeal that's essentially a legal side-show to the far-more-consequential James' fraud lawsuit is noteworthy, given that Trump has otherwise been clearing his busy docket. 

 Trump recently withdrew his last two remaining cases contesting James' lawsuit.

The first, a federal lawsuit in Florida that he'd filed in November and dropped on Friday, had sought the dismissal of James' lawsuit. The second, a federal appeal filed in Manhattan, had sought to invalidate James' three-year investigation into his company, and was dropped by Trump on Tuesday.

Trump's withdrawal of those two suits clears the way for a trial on James' lawsuit, scheduled for October, that his lawyer has promised Trump will attend and be "very involved" in.

Trump's lawyers, meanwhile, continue to spare no words in taking on the attorney general's office.

On Thursday night, attorneys for the 16 defendants named in James' lawsuit filed nearly 5,000 pages of response papers. 

The filings repetitively complain that James' lawsuit errs in repeatedly referring to "the Trump Organization," as her 222 pages do some 300 times. The Trump Organization is branding shorthand and not a legal entity, Trump's lawyers contend.