How Aaron Sells Won Friends and Lost Millions

For the past two decades, Sells has worked his way into the ranks of Boston’s most influential circles—from joining the Kraft family’s business empire to showing up at the ’Quin House alongside Karen Read. It’s a peculiar kind of fame: the sort where people who matter know your name, but no one wants to say it out loud. By his own admission, he moves behind closed doors, sits around exclusive tables, and shuttles between private clubs, forging connections and, as he calls it, making things happen. “That’s always been my thing,” he says. Yet despite this insider access, he remains largely unknown beyond Boston’s power corridors and is practically invisible on the internet—he’s arguably the city’s most successful ghost.

Armed with charm, a life-of-the-event persona, and a list of powerful contacts, Sells has launched multiple businesses with high-rolling investors, only to face allegations in court and around Boston that he diverted money into unrelated ventures and personal expenses, leaving business partners high and dry. “He’s charming and engaging, and his energy envelops you, and suddenly you’re out of X amount of dollars,” says one former business associate. Another associate tells me Sells has a way of making you feel like he would never slight you—until he does. “When you’re friends with him,” the person says, speaking anonymously for fear of retribution from Sells, “he’s out buying everybody bottles, and you think he’s the greatest guy in the world until you figure out that he’s buying bottles for everybody with their money that they gave him for a business.” Yet another former business associate says, “He seemed like a genuine guy. Turned out to be bullshit.”

In 2022, for instance, socialite and Mother Juice cofounder Laura Baldini and Paul Bernon—an investor and film producer who was once engaged to Bethenny Frankel of Real Housewives fame—and another business associate filed separate lawsuits alleging that Sells convinced them to invest in a health-food franchise called Broken Coconut. They said he took their money, used it for a separate business, and never returned it when the Boston location of Broken Coconut failed to open; all told, their claims totaled more than $300,000 in damages. Years before that, 28 people had accused him in a civil lawsuit of siphoning funds from the LLC operating the Greatest Bar restaurant into other ventures—a case that settled out of court. During COVID, he launched a mask business but faced default judgments totaling more than $1 million for allegedly taking customers’ money for masks he never delivered. Those are just some of the lawsuits he has faced. But the court cases tell only part of the story.

Other investors say Sells pulled a similar move—using invested funds for his own benefit—but they never sued him. When I asked them why, hardly anyone wanted to speak out. Those around town who say he burned them—and there are several—respond to his name with gasps. Most insisted on remaining anonymous due to their fears of his reprisal. (Sells says he has “no idea” why people would be afraid to speak about him.) Sources also warned me about meeting him, with some describing his gun collection and others saying he doesn’t forget perceived slights. (Sells has never been charged with any violent crime, nor did any of my sources accuse him of physical violence.) Yet there’s another reason for their silence, they say: Sells himself claims he has dirt on just about everyone in town. “[I have gotten people] so much business, connected so many people that begged me to, fixed so many fucked-up relationships, mended so many fences for people, got them out of so much trouble, covered for them, got their kids into schools they couldn’t get into, got them jobs,” he texted me at one point. “And forget about the skeletons [in the] closet and the bodies buried…I know all of theirs very intimately.”

Sells began accumulating that dirt on clients and future business partners—and his considerable connections—during five years as a salesman with the New England Patriots in the early 2000s. His job, Sells says, was creating fun for investors and clients—and he was good at it. “We knew he had a way about him,” remembers Lou Imbriano, former head of the team’s marketing efforts and Sells’s boss. “He has a gift of making people feel like they’re the only ones in the room. He knows how to build relationships, make people trust him, make people feel good.”

At lunch, with a tone of heartfelt earnestness, he tells me he’s aware he’s a frequent topic of discussion in Boston’s rumor mill. There are stories swapped on yachts, whispered in hair salons, and spread across the greens of golf courses. People speak ill of him, but it’s not how it looks—he’s not really that guy, he insists. “I don’t think I’m story-worthy,” he protests, gesturing with his fork. Indeed, I see the discomfort in his eyes as he picks nervously at a blackened chicken salad and is unable to touch his oysters. My questions are tying knots in his stomach, he says. Yet over the course of a marathon interview, as the restaurant fills for the lunch rush and then empties, Sells has an answer for every lawsuit and every allegation. “I never duped anybody,” he tells me, with a this-is-so-ridiculous-it’s-funny nonchalance. Later, he added, “Zero part of me has anything to do with con.”

When the interview comes to an end and we rise from the table, I am amazed that it has been more than four hours since we sat down for lunch. Time flew by in lively conversation that, despite its confrontational nature, was also, by turns, entertaining and funny. Before bidding me goodbye, Sells tells me he trusts I’ll be fair and that I am clearly “hyper-intelligent.” He later texts me to say he is “enamored” with my work as a writer. Other journalists have come calling before, he says, and all left satisfied with his answers. The one story published about his trail of lawsuits on Universal Hub was taken down after he implored the writer to have lunch with him. During our lunch, he offered me a meal on him at 1928—his fiancée’s restaurant, where some of his former investors have alleged he is hiding their money. I never took him up on it, but it’s hard not to wonder if perhaps Boston society’s best-kept secret isn’t an exclusive restaurant or a private club, but rather this charming dealmaker who’s left a trail of lawsuits and broken promises while hiding in plain sight for years.

Photo illustration by Benjamen Purvis

The moment that changed Aaron Sells’s life, he tells me, came during a rager at his parents’ Brookline home in the spring of 2002, when his phone rang with a Maine number he didn’t recognize. He was just a year out of Bates College, where he’d been lacrosse captain and a campus event promoter, but as an alumnus was banned from campus after an altercation at a bar. Sells was back home teaching at the Chestnut Hill School and coaching lacrosse at Tufts. When he answered, he says, he could hear a woman screaming in the background before a police officer’s voice cut through: Morgan McDuffee, his former roommate and lacrosse team cocaptain, had been stabbed to death while trying to break up a fight. Sells says that the traumatized witnesses—including several lacrosse players—had told police to call him for help.

Sells says he slumped to his knees in shock but quickly pulled it together and took charge. He emptied his house of revelers except a small group of friends and former lacrosse players, who piled into his car. The needle hovered around the 100-mile-an-hour mark nearly the whole way to Maine, where Sells remained for a few weeks after the school lifted his ban from campus so he could be there for his teammates in their grief, organize a foundation in his friend’s honor, and see to whatever had to be done.

A problem solver and handler had been born. And his skills were about to be noticed.

An announcement from the Chestnut Hill School went out to parents chronicling Sells’s absence from school after his loss, Sells says. Among those parents was Patriots owner Robert Kraft’s son, Daniel Kraft, who had also been a college lacrosse player. Soon after, at a school event, Sells says, Kraft approached Sells to offer his condolences. Then Kraft slipped Sells his card.

It was a perfect meet-cute between ambition and opportunity. Sells followed up, asking for a job. Despite having no experience in professional sports, he landed a position in the Patriots organization at one of the most pivotal moments in franchise history. Imbriano says Sells was soon assigned to his team.

The job description was deceptively simple: Figure out what sponsors wanted and make it happen. Sometimes, Imbriano says, that meant introductions or athlete appearances. Other times, “people would just ask for lit shit. I’d make it happen,” Sells says, declining to elaborate.

Still, the job’s most important requirement might have been helping clients fly under the radar. “There were definitely some [sponsors] who might have got in trouble with DUIs, and there may have been some people who might have had mistresses,” Imbriano explains. “We didn’t have juice to fix [DUIs]—that’s why you need a lawyer.” But if a wife came to an event, he said, “We’d make sure they wouldn’t be at the same place at the same time.” (A Patriots spokesperson categorically denied any organizational knowledge of inappropriate conduct during Sells’s tenure, dismissing any such allegations as fabricated or greatly exaggerated. The spokesperson emphasized that as a junior sales representative, Sells had no substantive interactions with the Kraft family and rejected any suggestion that ownership was complicit in the described behavior.)

When I ask Sells about this delicate choreography, he said he had “no comment” as to whether he helped cover up extramarital affairs while working at the Patriots, stating that it was a “broad question” and he can’t remember. “I’m not this magician that makes people’s shit go away,” he says. But, he says, “covering for them or helping them is different.” He says he knows people call him Boston’s own Ray Donovan—referencing the Southie-born Hollywood fixer in the eponymously named Showtime television drama—then immediately denies the comparison before insisting I series the series.

The lifestyle was intoxicating: “Extravagant dinners, private planes with clients, golfing all over the country, just entertaining, entertaining, entertaining,” he says. His name began appearing in Boston media as he moved between fundraisers and hot restaurants alongside CEOs, investors, and celebrities. His 2007 marriage to Liz Kelleher, daughter of philanthropist and Pyramid Global Hospitality founder and chairman Rick Kelleher, cemented his place among Boston’s elite.

After five years, Sells says, the constant late nights and schmoozing began to take their toll. He wanted independence. So he took his skills—and more important, his contact list—and struck out on his own, leaving the Patriots with Imbriano in 2006 to co-launch a sports marketing firm called TrinityOne. “If you can pull anything off, people start to ask you to do more and more and more,” Sells says. “With the Patriots, it was just like, ‘Throw it at him,’” he says, adding that that kind of work “sort of spun into my life thereafter.”

What spun out were dozens of LLCs filed in Sells’s name, three marketing agencies, and a string of restaurants—some of which would become the subject of lawsuits alleging fraud and deception. The problem solver, it seemed, would soon need some problem solving of his own.

Pat Piasecki

The business discount that would become a legal nightmare for Sells began in early 2018 with Scott Sartiano—a Columbia University tennis star turned Manhattan nightlife mogul, soon to hold the reins of the star-studded private club Zero Bond. But it wasn’t a glittering nightclub that brought Sartiano to Boston. He was interested in discussing something else with Sells: his lesser-known venture, Broken Coconut—a immediately-defunct quick-casual health-food chain that was said to have attracted famous fans when it opened in New York.

Sells saw an opportunity in bringing the immensely Instagrammable concept to Boston’s Seaport. To make it happen, though, he would need investors—people like Laura Baldini, the socialite behind the local Mother Juice chain. According to complaints from the civil lawsuits Baldini would later file, she invested “financial, reputational, and labor resources” to launch the Boston location. More significantly, Baldini’s verified complaint alleges, she agreed to lease a Newbury Street office under her personal name rather than a corporate LLC—a decision she would later claim was made “under false pretenses of Sells.”

Together, Baldini and Sells transformed a Seaport space into Broken Coconut’s Boston outpost—hanging signage and styling the interior in boho-beach décor. Then things fell apart quickly. According to Baldini’s lawsuits, they couldn’t secure a liquor license, unpaid invoices began piling up, and—unbeknownst to her—Sells had stopped paying rent on the Newbury Street office. The consequences landed squarely on Baldini: The office landlord placed a lien on her Ritz apartment and sued her for $100,000 in unpaid rent.

The case intensified from there. Shortly after launching her legal battle against Sells, Baldini’s attorneys filed an emergency motion to freeze Sells’s assets, and the court ordered Sells to put up more than $155,000 to be held in escrow until the case reached judgment. Sells didn’t put up the money or show up in court and was charged with contempt.

Sells’s Broken Coconut troubles extended beyond Baldini. According to another civil lawsuit filed against Sells, Paul Bernon—a Boston film producer and businessman—invested $50,000 in 2019, and Brendon Giblin, a Southborough builder, put in $100,000 the following year. Sells confirmed both investment amounts. According to their complaint, their agreements with Sells included what seemed like a reasonable safeguard: If Sells and the Broken Coconut LLC he set up couldn’t raise the full $800,000 needed to launch the franchise within a year, Bernon and Giblin would get their money back.

That safeguard proved worthless. In their complaint, Bernon and Giblin alleged that throughout 2020 and 2021, Sells provided “false and/or misleading” updates about the business’s financial status while never returning their money. Instead, they claimed, he diverted their investments toward personal expenses and unrelated business ventures. (Giblin dropped out of the lawsuit after Sells later filed for bankruptcy.) In Sells’s telling, however, Broken Coconut failed because “no one could have predicted there would be a pandemic, that all five locations in New York would shut down.” He denies the investors’ central allegation, saying he did not take money from Broken Coconut and invest it in other ventures, and after Sells filed for bankruptcy, the case was dismissed.

Broken Coconut wasn’t Sells’s first encounter with contract disputes. Nearly a decade earlier, in 2011, he and Peter Lucido faced a lawsuit over their management of the Next Place LLC, which owns the Greatest Bar in Boston. The complaint outlined a litany of alleged financial misconduct. Twenty-eight plaintiffs—all members of the Next Place LLC—accused the pair of siphoning finances from the Next Place to two unaffiliated businesses, the immediately-defunct Sea Dog pubs in Woburn and Northborough. The schemes allegedly included removing liquor from the Greatest Bar to stock the other businesses and paying employees of those ventures through the Next Place’s payroll. Sells was also accused of double-dealing by making the Next Place purchase insurance through his own company, where he allegedly profited as the broker.

That wasn’t all they were accused of putting on the Next Place’s tab—according to the complaint, the business was billed for Shaquille O’Neal’s appearance at a Sea Dog opening in Woburn as well as celebrity chef Michael Schlow’s salary as an “executive chef”—despite the Greatest Bar doing minimal food sales, according to the lawsuit. The lawsuit alleged that Sells served as Schlow’s agent, suggesting Sells may have profited from that arrangement as well, though Sells denies ever serving as Schlow’s agent. (Through a representative, Schlow declined to comment.)

When partners began asking questions about the finances, the complaint alleges, Sells and Lucido took decisive action: They fired the accountant, barred other members from examining the books, and deleted and whited-out QuickBooks entries. The matter ultimately settled out of court. Sells maintains he never had access to any of the books or QuickBooks, was a “sideline partner, not involved on the day-to-day,” and never took any liquor. He dismissed the allegations as jealousy from partners who “were pissed that we started doing other things without them.” But more financial disputes would follow.

Shaquille O’Neal (far right) at the grand opening of Sea Dog pub in Woburn—an appearance that Sells allegedly paid for using funds from another business. / Stuart Cahill / MediaNews Group / Boston Herald via Getty Images

In 2020, the pandemic offered Sells what seemed like a perfect business opportunity, rife with anxious customers willing to pay premium prices: the medical-mask industry. But the venture had problems from the start. A ProPublica article claimed his LLC Boston Capital Consultants was gouging customers on desperately needed protective gear. After denying to the reporter that he played a role in the company’s involvement in PPE, Sells launched a new entity, Safe and Clean Protection, to sell masks. Two companies alleged in separate lawsuits that they fell victim to an identical scheme: They sent Sells’s company money for masks that never materialized. Once again, Sells failed to appear in court, and judges ordered him and his company to pay combined default damages exceeding $1 million.

Sells claims he was the real victim in the mask business debacle, saying the vendor supplying his company failed to deliver and left him unable to fulfill orders. “I was new to the space and figuring it out as I went and got into some bad situations and [got] scammed,” he explains, though he and his attorney, Thomas Benner, were unable to provide records or any documentation to support Sells’s claim.

Where does the truth lie? When one examines Sells’s various business troubles, what emerges is a pattern of disputed narratives, where determining intent from circumstance proves elusive. I checked with a number of stakeholders in Sells’s businesses, one of whom had reached the opinion that Sells was diverting money from business accounts to his personal accounts at his marketing agency State6. While working at the company, that person examined State6’s profit-and-loss statements, and noticed that Sells seemed to be extracting money each month to cover his alimony payments. The same person, who told me Sells was expensing “any and all of his travel wherever he went” (including by helicopter), expressed doubt that all of those deductions were legitimately “business-related.” Yet another individual involved suggested to me that Sells also used money from State6 to pay for artwork at his immediately-closed restaurant Sons of Boston.

Sells disputes these characterizations entirely, saying it was the new CEO—referring to but not naming Joel Idelson, the company’s CEO for less than six months—who ran the company into the ground (an allegation that Idelson disputes), leaving him with more than $350,000 in debt when State6 closed. Without seeing the actual books, it’s hard to know who’s right.

These aren’t the only claims that have surfaced about Sells improperly using money for his own financial benefit. I spoke with five other investors and business associates who assert they lost money because, they believe, Sells transferred their investments into his personal accounts or failed to deliver promised services. None of the five ever filed a lawsuit to recover their losses—a silence that reveals something perhaps more telling than any court filing.

The reasons for their reluctance may illuminate the peculiar dynamics of Sells’s business relationships. One former business associate explains that Sells strategically targets investors who can’t afford the reputational damage of public litigation. “They are extremely well-known billionaires,” he says. “Losing $500k isn’t worth it for the damage it would do to their image.” Another business affiliate shared the sentiment, saying, “I don’t think they want to be publicly embarrassed that he ripped them off.” Whether he’s deliberately targeting people who won’t fight back or just happens to do business with conflict-averse wealthy people is unclear.

Others pointed to more personal concerns about confronting Sells, describing him as possessing a temper. “I’m a little concerned about what he might do,” says one associate who claims he invested half a million dollars in one of Sells’s enterprises and never recovered any of it. The fear factor, whether justified or not, appears to serve as its own form of protection against legal action.

Some creditors proved more willing to pursue formal remedies. In 2020, iHeartMedia filed a lawsuit against Sells and State6 for $69,177.02 the media giant claimed it had loaned the company. Sells failed to appear in court, and the judge ordered him to make a default payment of $71,122.31 to iHeartMedia.

The following year, Brett Hershey, whose investments include real estate, sued Sells over a $140,000 loan that was three years overdue. With 12 percent annual interest and additional quarterly interest compounding, Sells allegedly owed Hershey $277,627.29. According to Hershey’s attorney Sean Sullivan and the promissory note included in court documents, the loan agreement required repayment plus a 7 percent ownership stake in State6 for Hershey if Sells defaulted. Apparently, neither materialized. Sells would “represent via phone calls” that he would make payments, Sullivan says, but no money ever arrived. When Sells failed to appear in court, the judge issued a nearly $300,000 default judgment in Hershey’s favor. Meanwhile, the pattern of default judgments begs the question: Can Sells not afford to fight these cases, is it a legal strategy, or does he simply ignore them? Again, it’s impossible to know for sure.

Even Sells’s personal relationships became entangled in legal proceedings, though here, too, determining the full truth proves challenging. In December 2011, his wife of four years and the mother of his two children, Liz Kelleher, filed for divorce. Four months later, Kelleher filed an emergency domestic restraining order, citing Sells’s “harassing and intimidating” behavior. She alleged he was either watching her or having her followed (though Sells denies this) while incessantly calling and texting her. When Kelleher filed to renew the restraining order the following year, her filing mentioned Sells’s collection of approximately 20 guns.

By 2017, the divorce case had taken a turn: Kelleher filed an emergency motion to prohibit Sells from “disseminating, discussing, or publishing” her personal medical records or intimate photos or videos—as she alleged Sells had been threatening to do—and to return said records and media. Financial disputes compounded the personal drama. In July 2020, Kelleher claimed in probate and family court filings that Sells owed her more than $35,000 for child support payments. By 2022, according to Kelleher’s filings, that debt had ballooned to more than $500,000.

Faced with mounting legal and financial pressures, Sells found a solution. On the day he was scheduled to face trial in Baldini’s lawsuit, he filed for Chapter 7 bankruptcy. The filing automatically stayed all pending cases against him and eventually discharged his debts. Baldini, though, successfully fought to preserve one debt for rent and legal fees by filing yet another lawsuit.

Sells’s attorney, Thomas Benner, said the Department of Justice investigated his client’s financial records as part of the bankruptcy proceedings and “found no wrongdoing by my client and was satisfied during their investigation that Mr. Sells was truthful in his statements and allowed him to be discharged from his debts.” Sells maintains his bankruptcy resulted from a series of unfortunate events, though inconsistencies remain—he claims he repaid the majority of the original iHeartMedia loan, yet that debt still appeared on his official bankruptcy filing.

While the allegations paint a troubling picture, it’s still hard to tell whether Sells is someone deliberately ripping people off or just someone who’s bad at business and worse at relationships. Perhaps that’s the real story—how someone can skate by in the gray areas for years without ever facing real consequences, leaving everyone else to guess whether it’s all intentional or just a mess of bad luck and poor decisions. Still, the timing of the bankruptcy declaration raised an important question: Was Sells genuinely bankrupt, or had he engineered the perfect way out?

Sells’s ex-wife and three former investors alleged that he is hiding his assets in the popular restaurant 1928 Beacon Hill, which his fiancée, Kristin Jenkins, owns. Both Jenkins and Sells deny he has any financial interest in, or role at, the restaurant. / Joe St. Pierre

At 1928 Beacon Hill, gray-haired men nurse cocktails at the marble-topped bar beneath warm antique lighting and a wooden rowing oar suspended from the ceiling, while a grandfather clock marks time in the corner. Women with Botoxed foreheads discuss their salaried nannies from cushioned vintage leather booths, sipping beet- and ginger-infused cocktails. The restaurant pulses with authentic old Boston ambiance—and it’s become a smashing success, popular among local TV anchors, reporters, and public relations pros. It was also, Sells tells me, Karen Read’s preferred dining destination during her trial.

But beneath 1928’s stunning veneer lies a more complicated story. Sells’s ex-wife, plus three former Broken Coconut investors, claim in civil lawsuits and bankruptcy motions that this restaurant—officially owned by Sells’s fiancée, Kristin Jenkins—serves as Sells’s financial hiding place. Even the engagement ring he gave Jenkins before filing for bankruptcy, worth an estimated $75,000, has drawn attention in court filings.

The legal assault on 1928 began in earnest in 2022. Following the Broken Coconut collapse, Baldini filed two separate lawsuits—one targeting Sells alone, another naming both Sells and Jenkins as defendants. In the second lawsuit, Baldini alleged that Sells had devised an “elaborate scheme of complex LLC structuring” to conceal his assets. Baldini alleged in the lawsuit that Sells diverted Broken Coconut funds to 1928, and instead of pursuing a liquor license for Broken Coconut, he instead acquired one for 1928. Sells’s ex-wife echoed these suspicions during his bankruptcy proceedings, alleging he “holds an undisclosed beneficial interest in 1928.”

Both Sells and Jenkins denied under oath during Sells’s bankruptcy proceedings any financial entanglement between him and the restaurant. Jenkins testified that she financed 1928 entirely through her own resources, both her personal funds and those of her business Leonards New England, the esteemed Seekonk-based antiques dealership she inherited from Jeffrey Jenkins—her late husband who had previously been
her employer.

Jenkins reiterated in a statement that Sells “does not play a role in any of my businesses” and has had no impact or influence on 1928. The official denials, though, don’t appear to align with the evidence. Court records and depositions reveal a more complex relationship between Sells and 1928. When the 1928 Beacon Hill LLC was registered in November 2020, Sells was listed as a manager. Jenkins formally requested his removal just one month later. And in February 2021, when Jenkins appeared before the state board to transfer the liquor license from the previous restaurant owner, her attorney reportedly stated that she would also be aided by Sells.

The restaurant’s very name hints at deeper connections. The number 1928 had graced Sells’s license plate for decades before, he says, he recently got rid of it—it marks the birth year of his father. (Jenkins says it’s also the year her grandfather was born.) When 1928 first opened, a portrait of Sells hung prominently on the wall, styled like an 18th-century general’s portrait—the sort commissioned by aristocratic ancestors. Jenkins later testified that the painting was removed and immediately hangs in her daughter’s room. And despite their official denials, one restaurant regular describes Sells as a fixture at 1928, walking around the restaurant like he owns the place, “going from table to table buying drinks for people.”

The family connections extend beyond the name and portrait. According to depositions from Sells’s bankruptcy case, his nephew, Avery Sells—who previously worked for Broken Coconut—testified that he owns a 2 percent interest in 1928 through “a handshake discount.” Yet when questioned under oath, Sells claimed ignorance about his nephew’s role. “Him and I don’t talk about what he’s doing there,” he said. In a statement, Jenkins told me that Avery Sells is the director of operations for her restaurants, but does not have any shares. “I own 100 percent of all of my companies and will continue to,” Jenkins says.

The $75,000 engagement ring presents another contradiction. When I asked Sells about it, he told me he bought the ring for Jenkins but offered no explanation for how he financed the purchase. This account conflicts with his bankruptcy deposition, in which he claimed that the ring was gifted to him by his friend Ryan Caverly so he could propose to Jenkins. Jenkins, meanwhile, testified under examination that she didn’t know how Sells paid for the ring.

In fact, in the years leading up to his bankruptcy filing, according to Sells’s deposition testimony, Sells had orchestrated a series of transactions involving Caverly. The money flows were largely in one direction: Caverly transferred Sells $25,000 in November 2021, followed by another $7,500 the following month. Throughout the following year, he continued to send money Sells’s way. Then, in the spring of 2022, Caverly allegedly purchased the engagement ring for Sells. In his deposition, Sells characterized these transactions as legitimate business arrangements—and oftentimes just a friend helping another friend in need. “There’s no hidden money,” he testified, explaining they were attempting to launch a venture together. Meanwhile, according to Jenkins’s deposition, she has become Sells’s financial lifeline—covering rent on their Marlborough Street apartment, buying their meals, and paying their electricity bills.

The 1928 investment story contains yet another contradiction. Sells testified in court that he had intended to invest in the restaurant, but the deposit check he wrote to the building’s landlord in February 2021 bounced. “That’s when Kristin basically said, ‘I’m done. This is embarrassing. You’re out,’” he recalled. Court records and Jenkins’s deposition, though, show that one check from Sells for $34,691 did clear. It covered the deposit on 1928’s liquor license.

Sells told me that he “absolutely” did not take any money from Broken Coconut and invest it in 1928, and he dismisses the entire 1928 controversy as the vindictive campaign of a woman scorned. He reveals that he was romantically involved with Baldini but denies she was ever his girlfriend in any serious sense. One associate of his paints Baldini’s legal pursuit as infatuation rather than legitimate grievance. Whatever the reasons, the romantic entanglement has allegedly escalated into harassment, according to Jenkins’s court testimony. In a deposition given with Baldini present, Jenkins said that Baldini sent her emails about the Broken Coconut litigation along with “videos and photographs of Aaron and [Baldini] having sex.” Jenkins further alleged that Baldini had been lurking outside the restaurant “taking pictures and videos.”

Baldini and Sells both declined to comment on the sex-tape allegations. Regarding claims that she filed lawsuits out of spite, she said she believes “the pleadings speak for themselves. I feel bad for anybody who lost any money.” She added, “Anyone who knows me knows I fight for fairness and integrity,” and that she “certainly didn’t go to court for fun.”

The legal outcomes defy simple categorization. If criminal verdicts are black and white, civil agreements are taupe and gray. Baldini achieved what no other Sells creditor managed: She recovered her money. When she challenged his bankruptcy filing, the two parties agreed to settle under a rule stipulating that debts obtained by “false pretenses, a false representation, or actual fraud” cannot be discharged in bankruptcy. The final agreement was handled out of court, with both sides claiming they are barred from discussing its details. (Benner, Sells’s attorney, says Sells settled due to the risk that Baldini could have won on “technicalities” due to errors in his original bankruptcy filing.) Still, the central question—whether Sells is hiding assets in 1928—remains murky. Baldini’s case against Sells and Jenkins has not been decided, meaning no court has yet found that he had siphoned money into the restaurant. Yet the fraud case Baldini settled with Sells relied partly on evidence of his business entanglements with Jenkins, though Sells vehemently denies any funneling of investor funds into the restaurant. The ambiguity leaves open a tantalizing possibility: that 1928 is, indeed, where the broken dreams of Broken Coconut went to die.

Sells rocketed onto the Boston scene as a Patriots salesman in the early 2000s, forging relationships among the city’s high rollers. Opposite, court papers in multiple lawsuits against Aaron Sells allege a pattern of wrongdoing. / Pat Piasecki

By the time I sat down with Sells for our marathon lunch, he presented himself as a man who’d emerged unscathed from his legal battles. His troubles were behind him, he assured me, and his personal life was flourishing. He and Jenkins had just upgraded to a larger apartment. Sells described himself as “very happily married” to Jenkins—though he is not, in fact, married. When I pointed this out, he brushed off the distinction, saying he is devoted to Jenkins and was “all set with that side of the world.”

Regarding the professional side of his world, Sells painted an equally rosy picture. He claimed to be working part-time for public relations guru George Regan—who confirmed Sells “does some business development” for his firm but stated he was unaware of Sells’s legal quagmires. Sells also mentioned working for an energy broker called Inertia Resources. In a deposition regarding his bankruptcy, Sells said he is involved in “a very good lucrative career.” Throughout our meal, Sells worked his phone constantly, telling me he’s making deals as we speak. He works at Inertia with Caverly—the same man who, according to Sells’s deposition in his bankruptcy case, purchased the engagement ring Sells gave to Jenkins.

Sells maintains his legal troubles amount to nothing more than failed business ventures and the troublemaking of one persistent plaintiff. During our conversation, he projects an air of wounded innocence—kind, earnest, and at times genuinely sympathetic—even as his statements repeatedly contradict the sworn testimony in deposition transcripts he doesn’t seem to realize I’ve read.

Despite insisting repeatedly that there is no story, something in our exchange triggered his concern. He began pleading with me to consider his children and how an article might affect them. This tactic, I later discovered, had worked before. I tracked down Adam Gaffin, the Universal Hub reporter whose story about Sells had vanished from the news site. Gaffin explained that he rarely conducts interviews, relying instead on public filings, and almost never meets sources in person. But after his story went live, Sells’s attorney contacted Gaffin on behalf of his client and requested a meeting. At a sandwich shop, Sells told Gaffin the article was “harming” his children and affecting his family, Gaffin explains. “Legally, I know I had no reason to take it down,” Gaffin says immediately, but he relented anyway.

Once Sells realized I intended to proceed regardless, his approach shifted. He began probing for information—who was I speaking with, what were they sharing with me—in what felt like an intelligence-gathering operation designed to undermine my reporting. Then he made a startling prediction: I would not find a single source willing to talk. “I’m just shocked that there’s someone that’s going to talk, because there’s not one person involved in any of this that I don’t have like insane shit on,” he said.

“I can’t think of one person,” Aaron Sells says, “that I don’t have something really bad on, that wouldn’t cause their life to unwind quickly.”

In that moment, the true foundation of Sells’s influence struck me. His power doesn’t stem from wealth or connections alone—it also rests on secrets. Lots of them. “I can’t think of one person, and I’m being dead-honest, that I don’t have something really bad on, that wouldn’t cause their life to unwind quickly,” he told me. “If you’re a doctor, I know every bit of your insane drug problems. If you’re a very powerful person, I know every single affair. I know everything about everybody.”

The words seemed to carry an unmistakable menace, though Sells insisted he hadn’t meant them as a threat. He said he’d “counter” whatever damage this article might inflict by exposing damaging information about my sources. His prediction was stark in its certainty: Whoever provided me information was “gonna go down afterward.”

Later, as if what he told me at lunch wasn’t clear enough, Sells sent a text that laid out his insurance policy in explicit detail: “At the end of the day I have a safe with 12 phones in it since 2001. And all the codes and chargers to go with. Cause I knew someday someone (in this case apparently multiple) was going to do something stupid. Well, this is stupid. Every text, every picture, every ask, every favor, every ‘Aaron I’m fucked’, every disturbing shit they’re into, every affair who had to be paid to go away or made go away, Aaron I just got pulled over with a lot of coc** and they are arresting me (female of that bunch on that one), Aaron I’m in jail for dui this can’t happen please make it go away, every fucking shit show situation, please help…on and on…and that’s the light lifting.”

Then came his final pitch. Sells wasn’t trying to sell an investment this time, but something potentially more valuable to me: a different story entirely. One about secrets. About Boston as “a city of goldfish”—“the reality of this city and the people of influence swimming in it.” Depending on how this article about him turned out, he hinted, there might be an exclusive in it for me.

This article was first published in the print edition of the October 2025 issue with the headline: “How to Win Friends and Lose Millions.”