According to newly unsealed court documents, the 51-year-old billionaire allegedly shared confidential financial information about the sportswear giant with Ruhle when she was a Bloomberg Television news anchor. He also sought her assistance in countering concerns about declining sales.

The duo’s close ties were first reported by the Wall Street Journal in 2019, but now their relationship—which included trips on Plank’s private jet—is under the lens in court.

Plank, the current executive chairman of Under Armour, stands accused of providing Ruhle with “non-public financial information” about the company.

The lawsuit, filed by shareholders in 2017 in a federal court in Maryland, alleges that Under Armour artificially inflated its share price, resulting in losses for them.

Shareholders claim that Plank and his associates were aware of a decline in sales and so employed improper tactics to sustain the growth momentum.

This allegedly included enlisting Ruhle’s help to undermine a January 2016 report by Morgan Stanley which highlighted the weakening sales data.

A spokesperson for Under Armour told Fortune the documents have “no bearing on the case,” adding that Plank had “utilized confidential advice or counsel from a number of outside advisors from different fields of expertise, and that is what these documents show. Furthermore, none of the information was used improperly.”

Highlighting that a federal judge in the Southern District of New York has previously ruled against the plaintiffs, the company added: “The claims asserted by plaintiffs’ counsel are meritless and are being defended vigorously in the ongoing Maryland litigation, which has been pending for more than six years.”

Bloomberg did not immediately respond to Fortune’s request for comment.

An unlikely confidant

Plank has grown Under Armour—founded in 1996—from a moisture-wicking shirt maker for football players into a global brand with approximately $5.9 billion in annual sales and thousands of employees.

But the sportswear giant has struggled to move on from a scrappy company culture, having been embroiled in various complaints from strip club visits to inappropriate behavior by executives.

Now the latest filings around Plank and Ruhle’s relationship raise a host of ethical questions about the boundary reporters must maintain with the powerful people that they cover—and vice versa. 

Former and current executives reportedly told the WSJ Plank’s use of the jet and his relationship with Ruhle were among the many ways the CEO blurred the distinction between his personal and professional activities.

“There are clear lines between the company and Mr. Plank’s private interests, and he is accountable to the board for this,” Kelley McCormick, Under Armour’s senior vice president of communications told the publication.

During a deposition earlier this year, Plank, who stepped down as Under Armour CEO in 2019 before taking the role of chairman, was asked to describe the nature of his relationship with Ruhle. 

“She’s a confidant,” he responded, according to the WSJ. “I would give her counsel on her career and she would give me counsel on things I was dealing with that were either banking or media or human nature in relation.” 

When asked during his deposition about the Morgan Stanley report, Plank said the two “had an understanding of trust.” 

“She didn’t trade in this, her family doesn’t trade in this. She’s simply giving me input,” Plank said.

When Ruhle sat for her deposition, she admitted to taking at least two trips with Plank on his private jet: once from Cannes, France, to New York and another time from New York to Baltimore. 

When pressed on whether she took the trips as Plank’s friend or as a journalist, Ruhle said: “I was flying on his plane as myself, Stephanie Ruhle. I’m not really in a category as one or the other.”

The MSNBC anchor also confirmed that she had three phones: a work phone, a personal phone and a so-called “Kevin Plank phone”. 

“We were friends and I covered his company,” the anchor added.

Morgan Stanley email chain uncovered

On January 10, 2016, Morgan Stanley released a report in which it downgraded the rating of Under Armour stock and lowered its price target, citing a slowdown in sales trends.

Despite being in a “quiet period” that prevented public communication, Plank discussed privately with Ruhle how to dismiss the report, according to documents in the lawsuit.

The following day, Ruhle emailed Under Armour’s former communications executive Diane Pelkey for data that would contradict the report—and then advised they send it to media outlets.

″This content is perfect just in case anyone decides to cover the Morgan Stanley thing—it combats any risk of negativity,” Ruhle wrote in an email littered with typos to the executive, according to the WSJ.

Later that afternoon, Ruhle reportedly raised doubts about the data presented in the Morgan Stanley report on Bloomberg.

A couple of weeks later, when Under Armour reported positive quarterly results, Plank emailed Ruhle “look at that stock!!!” before allegedly helping her bag an interview with basketball player and Under Armour athlete Stephen Curry.

Court documents allege Plank told his communications executive in an email that the Curry interview was “a great thank you for being the only member of media to get UA’s back when [Morgan Stanley] came out against us.”

On Feb. 2, Bloomberg posted the interview, which included Ruhle playing basketball with Curry.