For the first time in nearly two decades running JPMorgan Chase, CEO Jamie Dimon will voluntarily sell stock in the bank.

The disclosure, in a securities filing Friday, detailed next year’s planned sales — pressuring JPMorgan (JPM) shares and the Dow Jones Industrial Average and highlighting why tracking trades made by executives involving the companies they lead should be an important part of every investor’s homework.

Dimon is setting up the trades through a predetermined plan that executives at publicly traded companies use to protect against insider trading accusations. It will mark the first time that the 67-year-old CEO has offloaded shares of JPMorgan for non-technical reasons, such as exercising options.  

The planned sales – amounting to roughly 12% of the JPMorgan stock owned by Dimon and his family – are being done for tax planning and personal wealth diversification reasons, the bank said. Both are common reasons for executives to sell stock in their firms. The bank also said Dimon continues to believe JPMorgan’s prospects are “very strong,” and his planned trades are not related in any way to succession. Such sales are often seen when CEOs get close to retirement.

As you can see, making sense of insider transactions can sometimes be a tall task.

When they buy, it’s generally seen as an encouraging sign by Wall Street — and there is, perhaps, no better example of this than another move by Dimon in 2016, when he purchased JPMorgan stock.

Fears of a weakening global economy sent stocks into a tailspin in early 2016, driving shares of JPMorgan down nearly 20% and the S&P 500 down more than 10% at their lows.

But that weakness didn’t last long.

The trajectory of the market changed just six weeks into the new year. That’s when Dimon disclosed — after the closing bell on Feb. 11, 2016 — that he bought 500,000 shares of the bank, worth about $26 million at the time.

Dimon’s stock purchase, intended to show confidence in the financial sector, has become legendary on Wall Street. It ultimately coincided with — or perhaps was the reason for — the closing lows for not only shares of JPMorgan in 2016 but also the S&P 500 overall.

Jim Cramer has since dubbed Feb. 11, 2016: “The Jamie Dimon Bottom.” JPMorgan finished up 30% that year, while the S&P 500 ended more than 9% higher — both huge turnarounds.

While executive stock sales — such as Dimon’s planned transactions next year — are not universally red flags, they can get complicated.

A New York federal judge warned JPMorgan Chase that he might find the bank in contempt of court if it does not speed up in producing evidence related to late sexual offender and money manager Jeffrey Epstein for lawsuits by an Epstein accuser and the government of the U.S. Virgin Islands, CNBC has learned.

Judge Jed Rakoff suggested in a notice that JPMorgan and two law firms representing the bank have been slow-walking in turning over documents and other evidence to plaintiffs in the case, under a process known as discovery, according to a source familiar with the notice.

The notice comes two weeks before JPMorgan CEO Jamie Dimon is scheduled to be questioned under oath by plaintiffs’ lawyers for the civil suits, which accuse his bank of enabling and benefiting from Epstein’s alleged sex trafficking of young women.

“The Court also wishes to note that it is concerned that JPMorgan is not moving more expeditiously to produce responsive documents,” Rakoff wrote in the notice, which has yet to appear on the public docket in the case in U.S. District Court in Manhattan.

“While the Court appreciates the large volume of discovery that is to be completed in this case, a company as large as JPMorgan and counsel as experienced as WilmerHale and Massey & Gail should be able to move with greater speed than what was revealed by this incident,” the judge wrote, referring to the bank’s two law firms.

“So JPMorgan is put on notice that further expedition will be needed on pain of being put in contempt of Court,” Rakoff wrote.

A JPMorgan spokesperson had no comment on the notice.

Epstein, who died from a jailhouse suicide in 2019 shortly after being arrested on federal child sex trafficking charges, was a long-time customer of the bank until 2013.

The lawsuits allege the bank allowed Epstein to remain a client despite evidence he was using millions of dollars he kept on deposit to facilitate his trafficking of girls and young women to his private island in the Virgin Islands and elsewhere.

Five years before JPMorgan ended its customer relationship with Epstein, he pleaded guilty in Florida state court to soliciting sex for money from an underage girl and served 13 months in jail.

Before his conviction, Epstein was friends with former presidents Donald Trump and Bill Clinton, as well as Prince Andrew of Britain.

JPMorgan denies any wrongdoing, and in its own civil complaint the company has said former bank executive Jes Staley would be legally responsible for any liability arising from its relationship with Epstein.

Staley spent three decades at JPMorgan and had close contact with Epstein — whom he considered a friend — over the years when Epstein was a customer.

Rakoff, in a court ruling published in early May, noted that “plaintiffs allege that Mr. Staley had first-hand knowledge of Jeffrey Epstein’s sex-trafficking operation.”

“Mr. Staley is alleged to have visited Epstein’s residences several times while that operation was ongoing, and, during these visits, observed [the Epstein accuser suing JPMorgan] ‘as a sexual trafficking and abuse victim,'” Rakoff noted.

“Plaintiffs further allege that Mr. Staley himself abused some of Epstein’s victims, including” the woman suing the bank, the judge wrote. That woman claims that “‘one of Epstein’s friends’ — whom she later identified as Mr. Staley — ‘used aggressive force in his sexual assault of her and informed [her] that he had Epstein’s permission to do what he wanted to her.'”

In his own court filing, Staley called the accusations against him “baseless,” and he has denied knowledge of Epstein’s sex trafficking.

Staley stepped down as CEO of British banking giant Barclays in late 2021 after an inquiry by a United Kingdom regulator into how he had characterized his relationship with Epstein to Barclays.

If you are having suicidal thoughts or are in distress, contact the Suicide & Crisis Lifeline at 988 for support and assistance from a trained counselor.

JPMorgan Chase CEO Jamie Dimon on Monday warned that a “very, very serious” mix of headwinds was likely to tip both the U.S. and global economy into recession by the middle of next year.

Dimon, the chief executive of the largest bank in the U.S., said the U.S. economy was “actually still doing well” at present and consumers were likely to be in better shape compared to the 2008 global financial crisis.

“But you can’t talk about the economy without talking about stuff in the future — and this is serious stuff,” Dimon told CNBC’s Julianna Tatelbaum on Monday at the JPM Techstars conference in London.

Among the indicators ringing alarm bells, Dimon cited the impact of runaway inflation, interest rates going up more than expected, the unknown effects of quantitative easing and Russia’s war in Ukraine.

“These are very, very serious things which I think are likely to push the U.S. and the world — I mean, Europe is already in recession — and they’re likely to put the U.S. in some kind of recession six to nine months from now,” Dimon said.

His comments come at a time of growing concern about the prospect of an economic recession as the Federal Reserve and other major central banks raise interest rates to combat soaring inflation.

Speaking to CNBC last month, Chicago Federal Reserve President Charles Evans said he’s feeling apprehensive about the U.S. central bank going too far, too fast in its bid to tackle high inflation rates.

The Fed raised benchmark interest rates by three-quarters of a percentage point last month, the third consecutive increase of that size. Fed officials also indicated they would continue hiking rates well above the current range of 3% to 3.25%.

Dimon said that while the Fed “waited too long and did too little” as inflation jumped to four-decade highs, the central bank is “clearly catching up.”

“From here we let’s all wish him success and keep our fingers crossed that they managed to slow down the economy enough so that whatever it is, is mild — and it is possible,” he added.

Dimon said he couldn’t be sure how long a recession in the U.S. might last, adding that market participants should assess a range of outcomes instead.

“It can go from very mild to quite hard and a lot will be reliant on what happens with this war. So, I think to guess is hard, be prepared.”

Dimon said the one guarantee he could be sure of was volatile markets. He also warned that this could coincide with disorderly financial conditions.

Asked for his views on the outlook for the S&P 500, Dimon said the benchmark could yet fall by “another easy 20%” from current levels, adding that “the next 20% would be much more painful than the first.”

Speaking to a roomful of analysts and investors in early June, Dimon said he was preparing the bank for an economic “hurricane” caused by the Federal Reserve and Russia’s war in Ukraine.

“JPMorgan is bracing ourselves and we’re going to be very conservative with our balance sheet,” Dimon said at the time. He advised investors to do the same.

Market participants are monitoring a highly anticipated inflation print on Thursday as well as a slew of corporate earnings.

JPMorgan is scheduled to release third-quarter financial results on Friday.

Shares of the bank are down roughly 33% year-to-date.