In May 2016, when the National Rifle Association hired Joshua Powell as its chief of staff, he was virtually unknown within the gun group’s headquarters. Unlike other top NRA officials, Powell, then 43 years old, had not worked his way up through the NRA’s ranks. Instead, he had been plucked from the 76-member board, where he’d quietly served for less than three years. He had no experience managing a large organization. Yet within a year, Powell took on still greater power. He was named the NRA’s executive director of general operations, becoming one of its top-ranking officials.

While continuing to serve as chief of staff, Powell now also oversees the NRA’s membership recruitment and its education and training programs. He is one of the organization’s eight officers, helping preside over its $343 million annual budget. Under the group’s bylaws, if longtime figurehead Wayne LaPierre were to become incapacitated, Powell would assume his duties.

Powell’s sudden ascension sparked widespread rumors among NRA staff that he was being groomed to one day lead the organization. He was a hunter, giving him a connection to the NRA’s sportsmen wing, and he possessed a high-end wardrobe, an expertly maintained five-o’clock shadow, and considerable charisma. According to court records, he also had business ties to two wealthy NRA donors, one of whom served as the gun group’s president in 2017.

But Powell’s tenure has been marked by failures. Membership revenues declined in 2017 by $35 million. And his signature achievement, the NRA’s Carry Guard program, which offers liability insurance to gun-owners, has attracted regulatory actions in multiple states that threatened its access to the basic banking services and corporate insurance coverage it needs to survive.

“Carry Guard is Josh’s baby,” a source close to the NRA told The Trace. “It was his brainchild, billed by Josh as an integral part of securing the NRA’s finances well into the future. But it’s a huge mess.” In recent court filings, the NRA claimed that regulatory actions taken by the New York Department of Financial Services over Carry Guard have cost it “tens of millions of dollars in damages.”

A Trace investigation into Powell’s business record, including a review of thousands of pages of legal documents and interviews with a dozen former associates, has uncovered a long history of mismanagement and financial irresponsibility. Prior to joining the gun group, Powell and his business ventures left a trail of defaulted debts, seized bank accounts, and jilted partners from Ireland to Montana, sparking more than 20 lawsuits for more than $400,000 from carpenters, modeling agencies, boutique gun-makers, and dozens of other vendors. (Of those, one is ongoing and one was dismissed; the rest ended either in a default judgment in favor of the creditors or an out-of-court settlement). Once, a lawyer he’d hired to represent him in a lawsuit over nonpayment sued him for nonpayment.

Yet even as a decade of near-catastrophic business failures reverberated in courthouses across the country, the NRA hired Powell for one of its most important positions. Powell did not respond to an email request for comment, but through a spokesperson, the NRA defended his acumen and his value to its mission.

“Josh oversees many key functions that are fundamental to the success of our organization,” said Andrew Arulanandam, NRA managing director of public affairs. “From the perspective of many at the leadership level, Josh is viewed as a savvy business executive and a steadfast defender of the Second Amendment.”

William A. Brewer III, a lawyer representing the NRA, issued a statement to The Trace acknowledging “difficulty” with Carry Guard but blaming it on Lockton Affinity, the program’s former administrator, which the NRA is suing for damages. Lockton did not respond to a request for comment.

To those who knew Powell from his former career, his travails at the NRA are unsurprising. What stunned them was that he was hired by the NRA at all. “When we heard he got the job,” said Cheryl Klonoski, who worked for Powell for several years as a retail manager, “we were all like, ‘Wow, didn’t anyone fucking vet this guy?’”

Powell’s biography on the NRA’s website says that he began his career at the Chicago Board of Trade “as a teenager attending Northwestern University.” It fails to mention that he never graduated. It claims that he and his wife and a friend “swayed a few votes” in favor of a concealed-carry law in Illinois by starting a PAC. It fails to mention that the PAC reported no financial activity during its one year of existence. The only thing the bio has to say about Powell’s professional career during the decade before his arrival at the NRA is that he “embarked on a consulting career for private equity firms and launched a number of startups.”

One of those “start-ups” was a very old-fashioned clothing catalog called J.L. Powell. The company began as a retail store in 2006, in Three Oaks, Michigan, a small lakeside town near the Indiana border. Soon, the company added its signature catalog — a heartland version of J. Peterman, filled with lush, rugged images of Powell himself living a dashing life of travel and sport in hand-stitched clothing. The merchandise — shoes, jackets, hats, knives, and the occasional $14,500 model airplane — was carefully curated to present a mythologized version of the modern-day adventurer. The catalog’s hero was, a lawsuit would later claim, “a character based on [Powell’s] personal lifestyle. In effect, he was his own avatar — a fictional version of the real Joshua L. Powell.”

A screenshot from an archived version of the JL Powell website, circa 2010. Powell is shown modeling his line’s clothes.

Multiple former business associates agreed that Powell is indeed a gifted salesman and creative force with a knack for translating his love of hunting and the outdoors into an aspirational lifestyle. But they say his business instincts ended there. “He had those creative skills,” said one former associate, “but he had no respect for the dollar, and a total disregard for the infrastructure around him. He just thought he could spend his way out of everything.” Klonoski, who managed the J.L. Powell store, said, “Josh never embraced his fiduciary responsibility to investors or business.”

Added a person familiar with the business: “The money that was forecasted to come in did not cover the money that was going out.”

By 2008, according to multiple sources, J.L. Powell was in deep financial trouble. Powell’s father-in-law at the time, Robert Boyle, provided a cash infusion of more than $1 million, according to court documents. A year later, the records show, no fewer than nine vendors and suppliers had filed lawsuits against J.L. Powell — and in many cases, Powell personally — for nonpayment. Six of the suits resulted in default judgements for the creditors. The rest were settled out of court. All appear to have been at least partially repaid, some after court-ordered seizures of funds.

“Things weren’t being handled or managed very well,” said Coreene Kreiser, a photographer and shoot producer who worked for J.L. Powell as a freelancer. “It wasn’t good.” She had to file a notice in small-claims court, she said, before the company finally paid her for the last shoot she worked on.

The following year, J.L. Powell booked losses of $783,000, according to financial statements filed in court. While the company bled money, internal records show that Powell paid himself more than $57,000 in advances on his salary.

“Josh used the brand as his personal expense account to fuel the lifestyle he wanted to live,” Klonoski said.

By 2010, J.L. Powell “was struggling financially and likely to go out of business” without additional capital, according to a subsequent lawsuit. The company was in default to 28 vendors, totaling $383,000 in outstanding debt, according to court records. That’s when an investment group called Blue Highways, led by a veteran catalog executive named Bruce Willard, who had previously partnered with Robert Redford on a Sundance-themed catalog, came to the rescue. Willard and his co-investors agreed to pour $2.5 million into the operation, demanding in return a majority stake and the right to exclusively use Powell’s name and image even if he left. In essence, Powell sold himself to save his company.

The new partnership got off to a rocky start, and was soon engulfed in five lawsuits. Powell’s “performance in his role as chief executive officer of JL Powell LLC began to deteriorate soon after the closing of the deal,” the new investors would later claim in court. Within the first year, Blue Highways discovered unspecified “breaches of representations and warranties” that cost the new venture more than $454,000, according to court records. Just seven months after Blue Highways made its investment, Powell needed more money, and Blue Highways obliged with a $500,000 loan. More such loans would follow, totalling $1.4 million by 2012.

In April of that year, J.L. Powell fired its namesake, but it continued to use Powell’s name and mystique to sell twill shorts. The acrimony and allegations built from there. By 2013, Blue Highways cut out Powell and his original investors after the company defaulted on the loans. The minutes of a January 2013 meeting of the company’s board, filed in court records, described Powell and his original funders as derelict: “[Powell’s] voluntary failure to engage or participate in this critical board decision… is consistent with [his] prior history with respect to financial investment and support of the company and management decisions of the board.”

Willard did not respond to repeated requests to comment for this story.

One year after he was fired, Powell launched a new catalog business called The Field. It targeted the same customers as J.L. Powell, with the same sort of high-end apparel and sporting goods from some of the same suppliers. According to a deposition of Powell, The Field was backed by Pete Brownell and Walter McLallan, two men closely affiliated with the NRA. Both are members of the Golden Ring of Freedom, an elite class of donors who have given a million dollars or more to the organization. Brownell, who owns a firearms accessory company, is a longtime NRA board member, and he served as the gun group’s president in 2017. Brownell and McLallan did not respond to requests for comment.

To judge by the volume of collections lawsuits it faced, Powell ran The Field the same way he ran J.L. Powell. The catalog was similar — a rough-bearded man in the “Officer’s Field Pant” sits outdoors, contemplative gaze fixed on the middle distance, a campfire in the background, a book called “Fine Wines” in his hand. And so were the demands for payment from bilked vendors. Between 2015 and 2018, four different firms sued The Field for more than $115,000 in unpaid invoices, according to court records. One of the suits is ongoing; the other three plaintiffs settled out of court, two of them after Brownell’s gun accessory company, which had been named as a co-defendant, made partial payment.

An image from The Field catalog, circa April 2013.

People who worked for The Field recall an atmosphere of utter disarray, disorganization, and bad faith. The business spawned an offshoot, a catalog called Grace Project that sold upscale yoga clothes. Cory Parolin, who worked as Grace’s digital marketing director in 2014, said, “Our Google AdWords got shut down on a regular basis because the company credit card would not go through.”

According to Nancy Flem, Grace’s creative director: “Money got questionable during the summer of 2014. The printers didn’t get paid, the pattern makers didn’t get paid, the people who provided the fabric for manufacturers didn’t get paid, and the model companies didn’t get paid. Once, when I was setting up a photoshoot, I had to personally pay $10,000 for a trailer because the company cards got declined.”

Powell, Flem said, always “promised that money was on the way, but it never happened.” She came to believe that Powell didn’t actually care about his failures to pay debts. “I remember going out to an expensive restaurant with Josh [Powell] and Dan Winders” — the company’s chief operating officer— “and three credit cards were declined. They were laughing as they tried to find a card that wasn’t maxed out.” (Winders declined to comment.)

Powell had “no understanding of business,” Flem said. “There was no strategy, sales goals, or projections.”

One of the lawsuits over unpaid invoices, brought in 2015 by Ford Models against The Field and Powell personally, is still active in Cook County Court in Chicago. Ford — which declined to comment through a lawyer — claims that The Field failed to pay nearly $65,000 for models used in catalog shoots during 2014 and 2015. The allegations follow a familiar pattern: Powell’s company didn’t pay its bills, and when Ford demanded payment, his employees promised to make payments but rarely followed through.

Documents in the case also offer a window into the profligate spending that went on under Powell’s leadership: The budget for one 11-day photo shoot in Palm Springs, for instance, included $25,000 in hotel costs and $3,000 for food. The photographer, Jessica Dant, who was also The Field’s creative director, was to be paid “$10,000++” for her work. In a deposition filed in the case last year, when Powell was 10 months into his executive role at the NRA, he acknowledged that he had a sexual relationship with Dant, who declined to comment for this article.

The pricey shoot took place in November 2014; just three months earlier, Lakeland Hospital in Niles, Michigan, had sued Powell personally for non-payment of a $3,700 bill. It would eventually secure a default judgement and seize the money Powell owed.

Despite The Field’s shaky finances, the Blue Highways investors considered it enough of a threat to sue Powell in April 2013 in a Maine federal court for breach of contract and trademark infringement. By using his name in catalogs for The Field, they argued, Powell had violated his agreement not to use his name or image to compete with J.L. Powell.

The litigation — which gave rise to the looking-glass case caption, JL Powell LLC and JL Powell Clothing LLC v. Joshua L. Powell — ground on for more than two years, climbing up to an appeals court and back. The Blue Highways investors filed additional cases in California, and Powell retaliated with his own lawsuit in Chicago. Just nine months into the initial lawsuit, though, Powell’s trouble paying bills caught up with him again: In January 2014 all four of his attorneys asked the judge for permission to drop their client, claiming that Powell “has failed to fulfill his financial obligations” to their firms, and that he refused to pay them even after they threatened to withdraw. They also claimed that they “had difficulty contacting Mr. Powell over the past several weeks” and that “such lack of communication has made it difficult to effectively represent Mr. Powell in this matter.”

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Powell managed to keep the attorneys on board, at least for a while. Fifteen months later, the same four attorneys filed an identical motion, saying again that Powell hadn’t paid them and wasn’t returning their calls. This time, the rift was irreparable. Three of the attorneys did not respond to requests for comment; a fourth declined to comment.

At a hearing in the case in June 2015, Powell called in by phone. He was now acting as his own attorney, though he had not secured permission from the court to do so. When the judge scolded him for failing to meet repeated deadlines to either retain a new lawyer or file with the court as a pro se, or self-represented, defendant, Powell replied, “I filed what I thought was all the correct paperwork.” The judge replied that he hadn’t, and Powell blamed an unspecified technical glitch: “I understand. And I — I can resend all that. I did it once and for whatever reason apparently it didn’t connect.” He also lamented that he’d “spent my life savings on this case.”

It was not money well spent. The litigation ended in July 2015 with a settlement permanently barring Powell from using his name or signature in The Field catalog or on its web site, and barring him for a year from using his name publicly in connection with The Field.

By then, the Blue Highways investors apparently decided that Powell’s name wasn’t worth so much after all. They began rebranding the business as “True Measure of a Man.”

The Field didn’t last long, either. Its Facebook page was last updated in March 2015, and in October 2017 its website went dark. By that time, the New York Department of Financial Services was already a month into its investigation into another Josh Powell venture: Carry Guard.

Additional reporting by Brian Freskos.