The National Rifle Association over the past two years has grappled with two separate sexual harassment allegations against Josh Powell, a senior official, including a case involving an employee.

The employee’s complaint was settled in 2017 using the nonprofit’s funds, according to three sources familiar with the matter. Earlier that year, Wayne LaPierre, the organization’s leader, had promoted Powell to executive director of general operations.

ProPublica could not confirm the settlement amount, which is not noted in the nonprofit’s public filings. In a statement, John Frazer, the NRA’s general counsel and secretary, told ProPublica that Powell denied the allegations.

“The NRA opted to confidentially resolve the matter in the best interest of all involved,” Frazer said.

The disclosure of the settlement comes amid a stream of reports alleging mismanagement and questionable spending by NRA leadership. The organization faces congressional inquiries and investigations into its tax-exempt status by attorneys general in New York and Washington, D.C.

Powell is a top adviser to LaPierre and is among the NRA’s highest-paid officials, with compensation of nearly $800,000 in 2017.

In a separate harassment dispute in 2018, Powell’s behavior toward a woman who works for Ackerman McQueen, then the NRA’s advertising firm, escalated tensions in their decadeslong business relationship and caused Ackerman to bar him from any further contact with its employees.

Ackerman told ProPublica in a written statement that the firm “formally declared to Mr. LaPierre that it would not have any more dealings with Mr. Powell.” Ackerman said there was “clear reason to believe supported by evidence that he sexually harassed one of our employees and we would not tolerate his further involvement with any of our employees in order to protect their right to a safe work environment.”

Ackerman said the NRA “refused to cooperate” in addressing the complaint against Powell. Instead, Ackerman said Powell received “the full support of Mr. LaPierre and the board of directors.”

Over the last four months, Ackerman and the NRA have been locked in litigation in Virginia state court, with the gun group accusing the firm of dubious billing practices and Ackerman countersuing for defamation. Before the legal dispute, the two entities spent four decades working closely together. Ackerman helped shape the NRA’s messaging and public image.

The NRA responded to Ackerman’s statement on behalf of itself and Powell. A spokesperson for the organization called the firm’s claim part of a larger “extortion demand,” in which Ackerman said the NRA “must withdraw” its lawsuit “or face a smear campaign that would include sexual harassment allegations against one of its executives. Ackerman is now delivering on its threat. We are not surprised.”

Ackerman said the NRA’s “false” narrative “grows more ridiculous each day,” and its response to Powell’s actions created what became an irreparable rift in the business relationship, which brought tens of millions of dollars annually to Ackerman. “We believe our decision to take this decisive action to protect our employees contributed to the program of retaliation against Ackerman McQueen, and NRA Board members were not being told about these problems,” Ackerman’s statement says.

But NRA spokesman Andrew Arulanandam said the organization “acted appropriately and swiftly” in response to the harassment allegation involving Ackerman. “The NRA removed Mr. Powell from his position as liaison between the NRA and Ackerman, and Mr. Powell had no further involvement with Ackerman.”

The spokesman called Ackerman’s harassment allegations “cryptic,” adding that they “first surfaced in October 2018, shortly after Mr. Powell participated in an effort to significantly reduce Ackerman’s budget with the NRA. Immediately, remarks allegedly made more than a year before became fodder for a harassment claim — accompanied by a demand that Mr. Powell be excluded from any further budget negotiations with the agency. The NRA committed in good faith to investigate the allegation, but the accuser and Ackerman declined to participate in any interview about the alleged incident.”

Despite recent negative publicity, the NRA continues to have broad support among Republican members of Congress and with President Donald Trump, who was elected in 2016 after the NRA spent more than $30 million to boost his candidacy. After recent discussions with LaPierre, in the wake of mass shootings in Dayton, Ohio, and El Paso, Texas, Trump has reportedly backed away from favoring more stringent background checks for gun owners.

After receiving a tip, ProPublica asked Ackerman to respond to questions about a harassment complaint involving one of its employees. The woman who filed the complaint did not respond to a request for comment.

Powell has served as LaPierre’s chief of staff since 2016. In December 2018, after the Ackerman dispute occurred, LaPierre announced to staff that Powell would step away from his additional duties as executive director of general operations and join the NRA’s legal team as a “senior strategist” in a high-stakes lawsuit that had been filed that spring against New York Gov. Andrew Cuomo and the New York Department of Financial Services.

Powell has long been a source of contention among NRA staff and even some board members. Before arriving at NRA headquarters in 2016, he ran two upscale clothing catalogs that were intended to appeal to wealthy outdoorsmen. Vendors working with Powell sued him on at least 20 occasions, alleging unpaid invoices totaling more than $400,000.

In 2018, Powell came under scrutiny from NRA accountants. In a document that compiled a list of “top concerns” for the board’s audit committee, which provides the organization with fiscal oversight, arrangements that involved Powell and posed alleged conflicts of interest were repeatedly flagged. The accountants noted payments to Powell’s father, a photographer, and referenced his wife, Colleen Gallagher, who in late 2017 was hired by one of the NRA’s top fundraising vendors, McKenna & Associates. An NRA spokesperson said in May that the audit committee was “aware of the relationship and approved the consulting arrangement with McKenna.”

In June, Robert Brown, an NRA board member, emailed LaPierre and Frazer about Powell. ProPublica obtained a copy of the note, which is addressed to Frazer. “John,” it says, “Since Wayne refuses to respond to my emails, plez pass on to him the message below.”

“Wayne,” the message reads, “At the last NRA BoD meeting, you promised me you were going to terminate that worthless scoundrel, Josh Powell, in 60 days. Well, 60 days have passed. When are you going to fire him?”

Brown declined to provide a comment for this story. “I do not discuss internal NRA politics with the media,” he told ProPublica in an email. “Period.”