Former President Donald Trump's history of making inappropriate or questionable comments on tape got another chapter on Wednesday with fresh revelations from his post-White House life.

The latest example emerged from CNN's exclusive reporting that federal prosecutors have an audio recording of Trump acknowledging he held onto a classified Pentagon document after leaving office. The tape seems unlikely to dent his political position as the frontrunner for the GOP nomination in 2024. But it could have real consequences in the legal limbo where he lives.

Most people recall the "Access Hollywood" tape of Trump using vulgar language to argue that "stars" can grab women. The emergence of that tape just before the 2016 election didn't hurt him politically. But he later defended that statement as true, "unfortunately or fortunately," in a video deposition, and jurors in New York recently found him liable for sexual abuse after the deposition was played back to them.

And then there's the recording of him asking election officials in Georgia to "find" votes to help him change the results of the 2020 presidential election. Those efforts to overturn President Joe Biden's win in the Peach State are part of an ongoing investigation.

This latest tape could also end up as part of a criminal case. The recording is in the possession of the Department of Justice special counsel Jack Smith, who's investigating the retention of national defense information. Smith's investigation has shown signs of nearing its end, although it hasn't resulted in any criminal charges.

So why is this revelation so significant?

"First of all, prosecutors love tapes," CNN senior legal analyst Elie Honig, a former federal prosecutor, told Jake Tapper on "The Lead" Wednesday.

"If you have a subject on tape, that's his own words, that's his own voice. The defense can't say, well, some witness is fudging the truth."

Trump on tape

The recording of the July 2021 meeting, which CNN has not listened to but was described by multiple sources, seriously undercuts Trump's longstanding argument that he mentally declassified material he took with him from the White House. It also adds his Bedminster club to the potential locations where Trump had classified documents after leaving office.

The recording of the meeting captures the sound of paper rustling, sources said, though it is not clear if it was the actual document in question. That raises questions about exposure of the document since attendees at the meeting included people who did not have security clearances that would have allowed them to access classified information, sources said.

Smith has focused on the meeting as part of the criminal investigation into Trump's handling of national security secrets, and prosecutors have asked witnesses about the recording and the document before a federal grand jury, CNN's Katelyn Polantz, Paula Reid and Kaitlan Collins reported.

In response to the report, a Trump campaign spokesman said "leaks" are meant to "inflame tensions" around Trump.

What is the document?

The recording also recalls the chaos at the end of his presidency. On the tape, sources tell CNN, Trump points to a classified Pentagon document to try to refute the idea that Chairman of the Joint Chiefs of Staff Gen. Mark Milley had been trying to stop him from starting a war with Iran.

In July 2021, journalist Susan Glasser had reported that, near the end of Trump's presidency, Milley had raised concerns about Trump trying to strike Iran and had told the Joint Chiefs to ensure Trump issued no illegal orders and that he be informed if there was any concern.

That New Yorker story outraged Trump. On the tape, he mentions the document, which he said came from Milley, in response to that story -- arguing that if others could see it, it would discredit Milley, sources said. (The document Trump references was not produced by Milley, CNN was told.)

The document's existence is hardly unusual. The Joint Chiefs of Staff has a directorate focused on developing and proposing strategies and plans for the chairman, and another that provides guidance about current plans and operations to commanders throughout the force.

"You could pick any country and scenario and there is likely a contingency plan," a US official told CNN's Haley Britzky.

It is even less unusual for Milley to have briefed Trump on those plans, the official added. As chairman of the Joint Chiefs, Milley's job is to advise and brief the president on his military options as commander in chief.

"That does not mean that Gen. Milley is a warmonger," Beth Sanner, a former deputy director of National Intelligence who was involved with intelligence briefings during her career, said on CNN. "Quite the opposite. I spoke to him many times during my role as an intelligence official, and he absolutely did not want to go to war with Iran."

CNN's report on the recording also includes the incredible development that investigators have questioned Milley, who is still the nation's top general.

An apparent contradiction

The most important thing here could be Trump's acknowledgment that the document is classified, contradicting his argument that he had the unilateral power to declassify things and take them from the White House.

During a CNN town hall in New Hampshire earlier this month, CNN's Kaitlan Collins asked Trump if he had shown anyone classified documents to anyone.

"Not really," he told her, adding, "Let me just tell you, I have the absolute right to do whatever I want with them."

He had said that any classified documents he had were declassified, which is apparently contradicted by the audio recording.

As CNN reported, Trump's comments on the tape suggested he wanted to share the information but was aware of limitations on his ability post-presidency to declassify records, two of the sources said.

Multiple legal clouds

The documents case is hardly the only legal matter hanging over Trump.

The former president, and the country he wants to lead again, needs a color-coded calendar to keep track of all the legal developments involving him -- and help separate potential trials and appeals from upcoming debate and primary dates.

Besides the ongoing investigations into the aftermath of the 2020 election, here's what else is looming over Trump.

His criminal trial in New York, which stems from the investigation into his alleged role in a hush money scheme, will coincide with March primary contests.

More immediately, there's an October 2023 trial for the New York attorney general's $250 million lawsuit against Trump, his eldest children and the Trump Organization. The Trump Organization was already convicted of criminal tax fraud in December.

He's been found liable in a civil case for sexually abusing former magazine writer E. Jean Carroll in a New York department store in the mid-1990s. Appeals are ongoing. But Carroll, seizing on Trump's comments at a CNN town hall earlier this spring, has asked a judge to amend her initial defamation case against him.