On Donald Trump’s desk, high above Manhattan’s Fifth Avenue, a pair of burgundy-colored letter trays sit side by side.
The left tray, if one is facing the desk, is the inbox; the outbox is always on the right. All day long for decades, a cadre of typically young, female assistants dropped manila folders into the inbox. And they carried away the manila folders from the outbox.
The folders held hard copy paperwork — contract and appraisal drafts, spreadsheets, printouts of emails and news stories, checks in need of signing — the life-blood of the Trump Organization, all flowing in and out of the ventricles of those burgundy boxes.
“I didn’t think it was my position to look inside” those folders, Trump’s longtime executive assistant, Rhona Graff, told investigators with the New York attorney general’s office last month, describing the inbox-outbox system while testifying that her boss had no business-document retention policy in the decades before trading his Trump Tower desk for the Oval Office Resolute Desk in 2017.
AG Letitia James, now winding up a three-year probe of the Trump Organization, would very much have liked to look inside those folders.
She knows how vital hard copy documents are, given that the computer-averse Trump ran his multi-billion-dollar company as if in the mid-20th century, shunning email and text chains, and relying instead on spoken and handwritten directives. 
But out of some 900,000 documents totaling 6 million pages now turned over to her probe by the Trump Organization, only ten — about 500 pages worth — bear Trump’s Sharpie-scrawled handwriting, her lawyers have complained in court documents and hearings over the past 2 years.
Upon leaving the box on the right, any handwritten directives once inside those folders appear to have largely vanished.
And at least some of the handwritten, Trump directives that have been turned over to the AG are hardly smoking guns. A few appended to a recent court filing included Trump’s terse, Sharpie markups of pictures of his properties and favorite golfers.
“Great,” Trump wrote on a series of old news photos of golf stars Arnold Palmer and Gary Player.  
A former Trump Organization employee suggested that any more weighty documents bearing Trump’s handwritten directives are unlikely to have survived.
“Is there a document retention policy on those documents?” the former employee said, speaking to Insider on condition of anonymity.
“The answer is no. In most cases you either threw it in the garbage or you threw it in the shredder.”
Notably missing from the AG’s assembled evidence are the leaf-pile’s worth of Post-it Notes that Trump’s top corporate lawyer, Alan Garten, has told probers his boss routinely stuck on documents when giving written orders.
“To my knowledge, we haven’t seen any documents that have Post-its on them,” Andrew Amer, a lawyer for the AG’s office, said during a May court hearing.
“That’s one of the odd things about the [document] production to date,” he said.
“And quite frankly, we’re still waiting.”
At the same hearing, Trump attorney Alina Habba repeated, with evident frustration, that every Trump Organization document the AG has demanded has been turned over. There is simply nothing more to give.
Any evidentiary stickies would have been scanned and submitted in compliance with the AG’s many subpoenas, Habba added.
But she also pointed out, quite reasonably, that Post-its are, by design, transitory.
 “I write notes to my assistants, I write notes to [law partner] Michael [Madaio], and I can assure you,” she said, “these are not going anywhere but in the round receptacle.” Habba declined to comment on this story, as did the AG’s office.
The Manhattan judge presiding over the AG’s probe, New York Supreme Court Arthur Engoron, is expected to rule soon on whether a costly, $10,000-a-day contempt-of-court order — Trump’s penalty for failing to fully comply with James’ subpoenas for his personal business documents — will be lifted.
So far, the contempt order has cost Trump $110,000 in fines, which the AG is holding in escrow pending Trump’s appeal of the order. The cost to Trump could rise past $300,000 in the unlikely case of the judge retroactively re-instating the daily fine.
“I understand we have a slight difference of opinion,” the judge told Habba at the most recent hearing on the matter, during which Habba again stressed that Trump has no more paperwork to turn over.
“I just think the opinion is a lot based on who my client is,” Habba responded. “And that’s concerning to me.”
As a Manhattan prosecutor, attorney John Moscow handled complicated white-collar criminal investigations. He’s been following the public court filings in the AG’s probe, and believes the lack of Trump documents is remarkable — and intentional.
Why else, Moscow asks, would a CEO run a multi-billion-dollar company on spoken commands and apparently long-vanished scraps and jottings, without creating a traceable, electronic record of his orders and decisions?
“The key takeaway from this is, he did business as if planning to defeat an investigation,” said Moscow, now a defense attorney with Lewis Baach Kaufmann Middlemiss. 
“You would expect to see fingerprints,” given that Trump was by most accounts a hands-on CEO, Moscow said.
“If there are none — and there are nearly none — that is evidence of a policy of wiping the fingerprints.” 
Even without the contents of that outbox — and despite zero apparent incriminating cooperation from his C-suite — James is moving forward, and appears to be on the brink of filing something big.
She has alleged in court papers that Trump repeatedly fudged the values of his properties on financial statements, loan applications, tax submissions and other official documents, many bearing Trump’s signature or that of his son, Eric Trump, who, as an executive vice president, signed the company’s Statements of Financial Condition post-2017.
Trump continues to be the sole beneficiary of the Trump Organization, the AG says, alleging that this high-balling and low-balling of its properties’ worth has earned him hundreds of millions of dollars in ill-gotten loans and tax breaks over the years.
James’ upcoming lawsuit against the New York-based company may seek to put it out of business entirely, and could well drop this summer, after Donald Trump, Ivanka Trump and Donald Trump, Jr., submit to questioning by probers in court-mandated, sworn depositions scheduled for mid-July.
Trump’s lawyers have steadfastly denied wrongdoing; Trump himself has called the probe a politically motivated and “racist” witch hunt. 
“There’s no New York law that says you have to keep your documents in general,” said Diana Florence, another former Manhattan prosecutor who handled major financial fraud cases.
“Many closely held family corporations will not have the same document-retention policies as a Fortune 500 company,” she told Insider.
“But what we have here is a company where the CEO was able to communicate exactly what he wanted without leaving a permanent record of it,” noted Florence, a former Democratic candidate for Manhattan DA now in private practice.
“It’s very 20th Century,” she added. “Everyone does everything electronically now.”
The AG won’t find “an employee handbook saying destroy all Post-it notes,” Florence joked.
Still, the lack of these notes, and of Trump’s handwritten directives in general, suggests a pattern, tiles in a “fraud mosaic” that the AG pieces together to an eventual jury, she said.
The AG, too, has suggested that the lack of Trump documents may come back to haunt him.
AG attorney Kevin Wallace’s voice turned ominous when Habba insisted during an April hearing — and for the umpteenth time — that “there’s really nothing left in his custody” for Trump to turn over.
“I’ll be frank,” Wallace warned. “If that’s all there is … it raises a bunch of other issues.” 
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