Dumpster Fire of the Vanities: John Menard, Steve Hilbert, and the Midwestern Nouveau Riche

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he appeared to be dressed for a funeral, and, in a way, she was.

Under steel-blue sky, Melania Trump descended a granite staircase in black stilettos, black overcoat, and black sunglasses. Behind her, a solemn procession of dour-faced briefcase carriers.

On November 14, 2013, the wife of Donald Trump, that cartoonishly coifed and cocksure presidential candidate, left the federal courthouse in downtown Indianapolis on the final day of testimony in a trial that was also a kind of memorial for a friendship that had died a painful, spectacular death.

Melania Trump’s company, Melania Marks Skincare, had been sued by Merchant Capital, an investment entity owned by John Menard, founder of the Menards home-improvement chain. Another plaintiff, New Sunshine, was a subsidiary tanning business Menard had recently pried from the clutches of Stephen Hilbert, an executive in Central Indiana. A decade earlier, Menard and his fiancee had vacationed with Hilbert and his wife at Mar-a-Lago, Donald Trump’s 20-acre estate in Palm Beach, Florida. Now Melania, a Slovenian glamorista and former model married to a rich and powerful man, was pulled between two other rich and powerful men—business partners gone bad.

At issue in the trial was a licensing agreement Melania Trump made for a signature line of beauty products with Indianapolis-based New Sunshine, whose CEO at the time, Steve Hilbert, was friends with her husband, Donald. Hilbert and Melania had big plans, including a distribution deal with Lord & Taylor and discussions with QVC, and Melania made appearances on The View and Celebrity Apprentice to promote the brand. But before they could get the “Melania” line off the ground, New Sunshine and its owner, Merchant Capital, rescinded the agreement and sued to void Melania’s contract. The Indianapolis court was also considering Melania’s counterclaim that Merchant Capital wrongly broke up her agreement with New Sunshine and—though she’d already received $250,000 just for signing—that she was due $50 million for lost royalties and damage to her brand.

With Melania Trump joining the fray, the feud was no longer just a regional skirmish pitting a flamboyant Hoosier millionaire against a meat-and-potatoes billionaire from America’s Dairyland.

What Melania Trump hadn’t realized when she signed with New Sunshine in 2012 was that just a few months beforehand, Menard had slapped Hilbert with a you’re fired! that would have impressed even The Donald. Hilbert called the termination letter from Merchant Capital “bullshit” and refused to leave.

Later, during Melania Trump’s trial, an attorney directed one former New Sunshine executive to recount the imbroglio. “How had Mr. Hilbert described to you whatever conflict there was between himself and Mr. Menard?” asked the attorney.

“Excuse my French,” answered the executive, “but he said he was in a world-class pissing match.”

That’s one way to put it. To date, at least a dozen lawsuits have entangled the men—along with their families, friends, lovers, and associates—in a bitter, years-long legal and personal saga. With Melania Trump joining the fray, and with the name of her New York tycoon husband dragged into the proceedings, the feud was no longer just a regional skirmish pitting a flamboyant Hoosier millionaire and his socialite wife against a meat-and-potatoes billionaire from America’s Dairyland. It had also become a critical mass of heavyweight egos, with jealously guarded private lives hung out on the courthouse clothesline. Messy financial and personal ties unraveled by nasty recriminations and endlessly pugnacious litigation. Allegations of inappropriate sexual advances and shady dealings. Fortunes made and lost.

While several of the main players in the ongoing tsunami of lawsuits provided statements through attorneys for this story, none granted full interviews—not surprising, given the risk of serving up even more ammunition for the other side to use against them in the proceedings. But the public court documents alone have revealed quite enough to fascinate those following the story, even as the litigants rack up legal fees and emotional tolls. More than that, though, the conflict offers a rare glimpse into an exclusive and lavish lifestyle, where money intermingles freely with friendship, business with pleasure, and presents a case study of a distinctive subculture—the Midwestern nouveau riche.

Steve Hilbert’s rags-to-Rolex bio is a story arc Horatio Alger might have rejected for being too hackneyed. A kid from Terre Haute, the son of a maintenance man and a telephone operator, he dropped out of Indiana State University after two years and, at the age of 19, peddled encyclopedias door to door.

As a salesman, Steve Hilbert found his true calling. He soon graduated from books to insurance policies, eventually launching Security National of Indiana Corp. in 1979. Over the next two decades, Hilbert pursued ever-larger companies to gobble up, allowing him to grow his startup from a few file boxes to Conseco, a multibillion-dollar insurance and financial behemoth in Carmel, Indiana.

As Conseco’s chief executive, Steve Hilbert became fabulously wealthy, earning a reported $119 million in 1997 alone. That was an era when rock-star CEOs ruled, and men in that rarefied orbit of conspicuous wealth gravitated together. In 1998, New York real-estate mogul Donald Trump, itching to buy Manhattan’s iconic General Motors Building but short on capital, saw in Hilbert a high-flying entrepreneur piloting a company on a buying binge. So Trump called Hilbert, and Conseco partnered with The Donald to acquire the property for more than $800 million.

Hilbert shared Donald Trump’s appreciation for the kinds of things the latter describes with his signature buzzword: class. He appointed his office in Conseco’s Carmel headquarters with a Christie’s-caliber catalog of Continental fineries and antiques. From an ornate circa-1790 French Directoire–period table, to a circa-1810 French Empire–period chariot clock of antico verde marble, the collection was valued at about $3 million.

Le Chateau Renaissance in Carmel, Ind.

It was the dawn of what some would call America’s second Gilded Age, and the bathroom fixtures in Hilbert’s home were literally plated in gold. At more than 20,000 square feet, on close to 40 leafy acres just north of Carmel’s uber-exclusive Laurelwood community, the estate was a brick-and-mortar billboard for the insurance titan’s wealth. The spread cost some $25 million to build, and Hilbert imported priceless artwork and skilled craftsmen who produced, among other finishing details, a cupola hand-painted with likenesses of the historical figure Hilbert most admired, Alexander the Great. Pacers Hall-of-Famer Reggie Miller is said to have practiced on the basketball court—a full-size, down-to-the-detail replica of the floor at Indiana University’s Assembly Hall—while preparing for the 1994 FIBA World Championships as a member of the second Dream Team. Indeed, the manse, which Hilbert dubbed Le Chateau Renaissance, and the famous parties he threw there, became the nexus of the north-suburban scene, the shiniest jewel in Carmel’s crown as the new-money capital of Indiana.

Hilbert’s knack for closing deals extended to marriage proposals, and in 1994, at the age of 48, he wed a vivacious 23-year-old brunette named Tomisue Tomlinson, after divorcing his previous wife, Louann. The apocryphal tale of how Hilbert and Tomisue got together is well known. “My first memory of Hilbert was a story that went through Indianapolis like wildfire,” says Eddie Cheever, a former racecar driver and team owner when Conseco was a sponsor in the old Indy Racing League. Hilbert was at a birthday party, which included a large cake. “A young, lovely lady jumped out and did what women do when they jump out of cakes at dinner parties,” says Cheever. “The kicker to the story was that he then went on to marry the young lady. Hard to forget that one. Racing is full of interesting stories, but that one takes the cake, so to speak.”

Hilbert played coy about that first encounter with Tomisue in a 1995 Indianapolis Monthly article. “I hate to talk a whole hell of a lot about how I met her, because I was married at the time,” he said. “We started talking and spending some time together … We fell in love, and the rest is history.” Then–IM staffer Sam Stall visited and interviewed the Hilberts at their home for a cover piece on the newlyweds. “He told me a story about how she’d worked in an antique shop in Florida when he ran into her,” says Stall. “He told me the antique-store story in a sort of a ‘wink-wink’ way.”

The IM article notes that Tomisue had recently attended a finishing school in New York, was taking French lessons and managing the household staff and social calendar, and drove a yellow Ferrari convertible, her favorite “summer car.” As Stall remembers, the relationship had strong parallels to My Fair Lady. “There was a lot of buffing and polishing going on,” Stall says, “almost as if she was following his lead.”

An original Monet hung over one of their fireplaces, but if Tomisue was giddy about her circumstances, she played it cool in the interview. “We didn’t want it to be so froufrou that it doesn’t even look lived in,” she said of the house. “Steve and I wanted something that was simple but elegant.” That same year, Steve Hilbert bought his first racehorse and named it Tomisue’s Delight. (He would later run two others, Stephen Got Even and Parade Ground, in the Kentucky Derby.)

Steve and Tomisue Hilbert at an Indiana Pacers game

Trophy horses—and trophy wife? Say what you will, but 20 years later, the marriage stands as Steve Hilbert’s most enduring. Tomisue would prove a loyal partner when times got tough—and they did. In 1998, with Conseco at its zenith and Steve Hilbert’s Midas touch unquestioned, he swung a deal for the company to buy Green Tree Financial, a mobile-home lender, for more than $6 billion. Wary of the sticker price and the lender’s rose-tinted accounting, Wall Street pummeled Conseco for the move, and the stock price plummeted from $58 when the purchase was announced to a few dollars per share in 2000. Facing a full-on shareholder revolt, Hilbert resigned.

Unlike some of the more egregious corporate excesses of the era, Steve Hilbert’s worst sin might have been optimism. While other CEOs looted the corporate treasury and touted company stock while quietly selling off their own, Hilbert doubled down on his stake in Conseco. By the time of his ouster, he owed almost $200 million in loans from the company or from banks whose loans Conseco backed, money Hilbert used to accumulate shares. When the bubble burst, Hilbert was on the hook for all of it, and his portfolio was worth a fraction of the debt. Even his $53 million severance was reportedly preceded by an emergency $23 million loan he took from the company to make a margin call. Just like that, the man who had started out with a dream and a smile to build a $60 billion conglomerate wasn’t simply back at square one. He was looking into the abyss.

Around the time Steve Hilbert was hawking encyclopedias as a young man in Terre Haute, John Menard was building pole barns in rural Wisconsin. His father, John Sr., had taken up dairy farming, a kind of second career. Junior went off to school at the University of Wisconsin–Eau Claire and studied business. He got into contracting to help pay for college, erecting agricultural buildings around the countryside. But his big breakthrough came when he discovered that customers were willing to buy construction materials from his inventory at a premium on Sundays, when the local lumberyards were closed. Retail was the ticket, and in 1972 he opened his first Menards store. By the 1980s, nearly 50 locations dotted several states.

While guys like Hilbert were getting rich with splashy acquisitions, Menard amassed one of the greatest personal fortunes in the United States the hard way, through a million little cash register ka-chings at his home-improvement stores. Always the country wheeler-dealer at heart, Menard obsessed over the day-to-day minutiae, personally negotiating purchases of overstock lots from vendors and other retailers and then moving the merchandise cheap at his own outlets.

Menard’s hands-on approach extended to auto racing, his primary extracurricular venture and passion project. In 1982, a Menard-backed car qualified for the Indianapolis 500, which would both allow him to compete on auto racing’s biggest stage and rev up the visibility of his fast-growing chain. As a team owner, Menard became a fixture in Indy-car racing and later in NASCAR, where his son Paul is a regular driver on the Sprint Cup circuit. Menard’s autosports enterprise was virtually indistinguishable from his retail concern, as he looped store vendors into sponsorship agreements on his racecars.

It’s tempting to imagine that for the rawboned Menard, guys like Hilbert were equivalent to the cool, well-dressed town kids a farm boy watches from afar on his first day in high school.

In 1998, as Conseco and Donald Trump were buying one of Manhattan’s most prestigious office towers, Menard was working on a more modest deal with Indy-car driver and owner Eddie Cheever in the weeks before the Indy 500. “By the start of May 1998, we hadn’t been successful in landing the main sponsor and were grossly underfinanced,” Cheever recalls. At the last minute, a snack company called Rachel’s offered to step in. But instead of money, they ponied up product. “I got on a plane to Eau Claire hoping to meet with John and try to convince him to buy all the Rachel’s potato chips,” says Cheever, previously a driver for Menard’s Indy Racing League team. “After some haggling, Menards had a lot of Rachel’s potato chips and a big Menards sticker on our car, and we had a check that allowed us to continue our May.” Talk about a win-win: Cheever finished the 500 in first place, and Menard got a load of product to mark up on his shelves.

In racing, as in retail, Menard might have been even more serious about saving money than making it. “I changed hotels when I was doing some work for Team Menard in Eau Claire, and the one I chose was a handful of dollars more expensive,” recalls Cheever, who now works in international development and procurement for Menard, Inc. “To his credit, he let me argue at length, and then he explained, in detail, why it was my expense and not Team Menard’s. That was that.”

Menard seems to have pursued cost-savings in at least one arena other than racing. In 1997, the State of Wisconsin charged him and Menard, Inc. with numerous environmental violations after an investigation uncovered attempts to forgo proper waste disposal. In one instance detailed in a lengthy criminal complaint, a Department of Natural Resources official observed Menard pulling into the driveway of his home on the outskirts of Eau Claire with four garbage bags in the back of his red GMC pickup—ostensibly to put them out with his own household garbage.

According to the investigator’s report, when asked about the bags, Menard “replied that he had his truck washed at about noon that day and that maybe the person that washed the truck put them in there,” and that “he really did not know that the bags were in the back of the truck until just now.”

After the investigator seized the bags and had the contents tested, he discovered they contained incinerator ash with high concentrations of arsenic and chromium. A Menard, Inc. employee told the investigator the boss was making similar trash runs every Tuesday. The company entered no-contest pleas to multiple felony counts of unlicensed transportation and disposal of hazardous wastes, and agreed to cough up $1 million in fines, pay $500,000 to a DNR trust fund, and donate $50,000 to a waste-reduction and recycling nonprofit.

A hefty fee for hauling ash in Eau Claire. But it was nothing compared to the pile Menard would one day lose in Indiana.

When John Menard and Steve Hilbert went into business together in the 1990s, they were the two biggest fish at the Indianapolis Motor Speedway, that crossroads of high-tech, high-dollar racing and lowbrow culture. Hilbert was throwing money around to put Conseco’s name on things. Menard managed to cajole Hilbert into sponsorships for his IRL team. By 2000, Conseco was paying Team Menard $10 million for the privilege of being its primary season-long sponsor.

It’s difficult to see what the two might have had in common outside of racing. Menard, a notorious skinflint and crank, grew up working construction and sold hardware. Hilbert was a tanned, smooth-talking salesman, a pursuer of pleasure, the life of the party, a conspicuous spender. Hilbert hung fine art at Le Chateau and drove a Ferrari Testarossa. Menard lived in a modest, wood-sided ranch house and drove a pickup truck.

Somehow, the two hit it off. Maybe they understood one another in a way only Midwesterners with fabulous newfound wealth could—two proud, self-made alpha dogs driven by ambition. Or maybe it was precisely because they were so temperamentally different that Menard saw something in Hilbert to admire and aspire to—hardworking and successful, but groomed, a glad-handing symbol of the ’90s executive lifestyle. “There are certain people who have that kind of energy coming off them,” says IM’s Sam Stall. “Not just that you believe them, but you want to believe them. That’s a power, and I think Hilbert had that.” It’s tempting to imagine that for the rawboned Menard, guys like Hilbert were equivalent to the cool, well-dressed town kids a farm boy watches from afar on his first day in high school.

Not long after Steve Hilbert made Conseco’s largest-ever sponsorship commitment to Menard’s race team, however, the Carmel businessman’s fortune ran out. After Hilbert left Conseco, in 2000, his loans from the company came due, commencing what would become a chronic condition of the Hilberts’ post-Conseco life: protracted, high-stakes litigation. Conseco foreclosed on Le Chateau, forcing the Hilberts to “downsize” to a 14,000-square-foot Carmel McMansion in Laurelwood. (Another self-made Hoosier millionaire, automotive-lubricants baron Forrest Lucas, bought Le Chateau for $3 million in order to use it as a party venue.) In 2003, new Conseco management came after Hilbert, seeking repayment on the $162 million in loans he’d taken to purchase stock, and a Hamilton County judge later entered a judgment in excess of $60 million.

Nevertheless, shortly after exiting Conseco, Hilbert, along with wife Tomisue, invested in Carmel-based Haverstick Consulting, a federal contractor that provided a diverse range of services, from Navy rocket systems to staff training at NASA. After a few years, the company had revenues of more than $100 million. The Hilberts brought racing buddy Menard in as an investor.

But it was Menard who got the Hilberts back in the game for real. In 2005, with Conseco hounding him for repayment, Steve Hilbert and Menard agreed that, with an influx of Menard’s capital, Hilbert could identify and acquire companies with “growth potential.” Through Merchant Capital, Menard—slow to part with money yet eager to earn more—was to pump up to $400 million into a newly formed investment vehicle, MH Private Equity Fund (“M” for Menard, “H” for Hilbert). Then he would give the Hilberts the keys.

What’s a bit of caviar and bubbly, Menard might have asked, compared to the bailout he had given the Hilberts?

Although Steve Hilbert was the one-time Wall Street whiz and Forbes-list dandy, in MH Private Equity’s operating agreement, Tomisue was named as the manager of an affiliated entity, MH Equity Managing Member, created to administer the fund. And it was she, not Steve, who executed the document along with John Menard. The agreement also established a 20 percent equity share in the fund for MH Equity Managing Member, whose “capital contribution” was $1. Steve would run the operation, taking compensation under the terms of a byzantine fee schedule.

Conseco’s lawyers viewed the setup with suspicion. In a 2006 court filing, they alleged that Hilbert had figured out how to make millions while evading financial obligations to his former company, namely by deferring income and squirreling away assets in Tomisue’s name. “It is [Steve] Hilbert who is providing the investment and management skills,” read the complaint. “And—make no mistake about it—it is Steve Hilbert who is being compensated for these efforts.” One Conseco attorney alleged in The Indianapolis Star that the Hilberts’ arrangement with Menard amounted to “yet another example of the fraudulent activities by the Hilberts,” and claimed that Tomisue had “no role in identifying, reviewing or executing investments for the fund.” One of Tomisue’s lawyers, quoted in Investment Dealers’ Digest, retorted that although Conseco was trying to portray her client as a “shill,” she was, on the contrary, “a very smart and active woman at MH Equity” and that “Conseco obviously believes that women have no value.” The lawyer called Conseco’s claim “legally deficient but, more important, factually incorrect.”

“Steve and I have always considered ourselves to be equal partners in all aspects of our marriage,” says Tomisue Hilbert in a statement provided to IM. “Like most spouses, I believe I also provide valuable advice and assistance to Steve and others by meeting with his business associates and promoting his business relationships. I also hold business interests of my own.”

Tomisue did spend quality time with the folks she was buying from. In just one example of the Hilberts’ apparent affinity for mixing business with pleasure, in 2006, MH Private Equity bought Sunshine Holdings, an Indianapolis company that made tanning lotion, from Trevor and Edna Gray, who also owned a home in Laurelwood and socialized with the Hilberts. Tomisue even joined the Grays, both avid sportspeople, for hunting and archery practice.

The Hilberts socialized with Menard as well, and as their business ties grew increasingly intimate, so did their personal relations. The home-improvement kingpin and his then-fiancee, a lawyer named Debra Sands who worked for Menard, Inc., began hanging out with the Hilberts, lunching together in Indianapolis, and, according to court documents later filed by Tomisue Hilbert, “The two couples enjoyed each other’s friendship and quickly became close personal friends.” They often vacationed at the Hilberts’ home in St. Martin, Le Chateau Des Palmiers, which, according to one real-estate listing, was a “world-class estate” that “embraced the spirit of the Caribbean with the elegance of a fine French hotel.” Anna Nicole Smith and an E! network crew reportedly camped out there in 2004, and the guest list has included not only NBA stars, the ad boasts, but also “some of the world’s most powerful people, including Donald Trump, Melania Knauss [Melania Trump’s maiden name] and of course, many Hollywood celebrities.”

Tomisue would later claim in court filings that Menard often arrived on these outings without much cash, carried declined credit cards, and generally lived it up on his hosts’ tab. For his part, Menard has said in a deposition that he returned the favor: Even if he never paid for a thing on trips to St. Martin, “neither did Mr. or Mrs. Hilbert when they visited up north at the lake.”

In any event, Menard could be forgiven if he felt entitled to a little wining and dining. What’s a bit of caviar and bubbly, he might have asked, compared to the bailout he had given the Hilberts?

The Hilberts had little reason to complain. For them, the following few years must have felt like old times. They reached a settlement with Conseco in 2006 and went to work with Menard’s money, dropping $36 million on the Michigan publisher of Entertainment coupon books, according to court records, and close to $200 million to buy tanning-related companies, including ETS Tan, Helios, and Australian Gold, which make tanning beds, salon-management software, and tanning-bed lotions and creams, respectively. In 2007, the Indianapolis Business Journal trumpeted that New Sunshine, the entity the Hilberts created as a parasol over MH Private Equity’s various tanning-industry acquisitions, was making Indianapolis the “world’s tanning-bed capital” and that Steve Hilbert was “tanning’s new king.”

But the sunny times didn’t last. With MH Private Equity seemingly thriving, the Hilberts and Menard formed another investment vehicle, MH Private Equity II, through which Merchant Capital wagered $200 million on Centaur, which owns Hoosier Park in Anderson, Indiana, and planned to add slot machines to the horse track. When Centaur fell into bankruptcy in 2010, Merchant Capital’s stake disappeared in a cloud of dust.

By 2006, Menard had turned his attention to a new love, a woman named Fay Obiad. Seeking a portion of the assets Menard had acquired since they got engaged, Menard’s ex-fiancee, Debra Sands, sued Menard, Menard, Inc., MH Private Equity, and several other companies, and petitioned the court to subpoena Steve Hilbert. The Hilberts, once friendly with Sands, found themselves embroiled in personal turmoil with Menard—a preview of things to come.

Apparently unperturbed, the Hilberts kept pushing their tanning products. In 2011, they played the Trump card, appearing on Celebrity Apprentice to pitch Australian Gold, which Hilbert described as “one of the most exciting, fastest-growing beauty companies” in the nation. On the show, contestants competed with alternative marketing plans. Gary Busey’s group barely lost out to a team led by La Toya Jackson.

What happened next depends on whom you believe, a matter of dispute in courts of law to this day. In the Menard side’s version, outlined later in court documents, he started having misgivings in early 2012 about the management of the companies under the MH Private Equity funds. He brought in outside auditors to draw up valuations, and they showed the entire portfolio was worth a few hundred million dollars less than what Merchant Capital had invested.

Merchant Capital withheld its annual payment covering MH Private Equity’s operating expenses and then cleaned house, canning not only Steve Hilbert but various other employees with personal ties to him, including Hilbert’s son, Todd, who worked at Australian Gold. Menard later described the incident in a deposition: “I met with Todd out of respect for Steve, ’cause I felt if someone was going to let Todd go, it should be me. It’s probably old-fashioned and foolish, but I felt that, so I talked to Todd. I said I felt very badly about this, but we cannot have you being the person that has the keys to the bank account, the electronic authorizations and so forth, the Treasurer, if you will … of New Sunshine, Australian Gold under the circumstances, and he said he understood, and we parted friends. We shook hands and he left.”

Australian Gold also dismissed Lisa Trudeau, the wife of former Indianapolis Colts quarterback Jack Trudeau and a friend of Tomisue Hilbert’s, who was involved in marketing and product development. Former New Sunshine president Eric Weber would later testify that he received his notice of dismissal via email shortly after meeting with the Kardashian sisters in California to discuss a product deal. The email came from his replacement, Matt Cotton, who before being appointed to the job was managing a Menards store in Avon, Indiana.

When Steve Hilbert refused to abandon his post as chief executive at MH Private Equity, Menard, Inc. and Merchant Capital sued him and the management entity controlled by Tomisue for fraud and breach of contract, among other things. Filed in 2012, Merchant Capital v. MH Equity Managing Member alleged that the Hilberts “breached their fiduciary duties,” causing the companies under the two MH Private Equity funds to lose nearly $345 million in value—78 percent of Merchant Capital’s initial investment. “At the same time,” the suit continued, “defendants have pocketed millions of dollars in ‘management’ and other fees.” The plaintiffs sought, among various things, unspecified “damages resulting from defendants’ misconduct.”

The formation of MH Private Equity “was an investment opportunity that Mr. Hilbert and Debra Sands presented in a very compelling manner at the time,” according to a statement Menard and his attorney provided to IM. But Menard came to believe that Hilbert and Sands wanted to “manipulate and defraud” him into supporting the transaction, as alleged in the initial complaint filed in Merchant Capital v. MH Equity Managing Member. In another filing, Menard claimed that shortly before signing the agreement forming MH Private Equity, he had actually tried to back out, until Sands became emotional and pleaded with him to follow through. So Menard gave in, reluctantly, and closed the deal.

Sands’s response to Menard’s allegation? “She denies it,” says Daniel Shulman, her attorney. “It’s not true.”

Steve Hilbert countersued, denying the claims of wrongdoing and arguing that Menard wanted to turn what was essentially a contract dispute “into something far more complicated and sinister.” The Hilbert side filed an answer to the allegation that Steve was in cahoots with Sands, agreeing Sands “became emotional” before the formation of MH Private Equity but positing that if Sands did pressure Menard by telling him he was “obligated” to proceed, “Menard knew it was untrue.” What’s more, the Hilbert side continued, Menard had the opportunity to propose revisions to the agreement before it was finalized, and the Hilberts consented to the changes.

Furthermore, Steve Hilbert’s counter-claim contends that Merchant Capital’s valuations of the companies under the Hilberts’ management were “dramatically understated,” and that Hilbert “offered to purchase Merchant Capital’s interest in Fund 1 for $150,000,000—20% more than the higher of the independent valuations and almost double the lower. Merchant Capital rejected the offer.” As for Merchant Capital’s loss in the Centaur deal, the Hilbert side answered that “John Menard, Menard [Inc.], and Merchant Capital knew—or had the reasonable opportunity to know … the material risks of the $200,000,000 equity investment in Centaur.”

Tomisue Hilbert filed a suit of her own against Menard and Merchant Capital, claiming Menard committed “breach of fiduciary duty, aiding and abetting breach of fiduciary duty,” and “tortious interference with prospective business relationships and opportunities.” The suit also made personal allegations that in Tomisue’s dealings with Menard, she suffered “intentional infliction of emotional distress, battery, attempted battery, assault, and attempted assault.” She sought unspecified “substantial compensatory and punitive damages.”

In Tomisue Hilbert’s version of events, outlined in a detailed complaint filed in Hamilton County in 2013, she and her husband were vacationing with Menard and his wife, Fay, over Memorial Day weekend in 2011 in St. Martin. Although Tomisue had known Menard for years and was fond of him, on this occasion he seemed to act differently than normal. He told her that he “no longer liked working, was tired of pleasing his customers, and had decided he wanted to live his life fully and fulfill his sexual urges.” According to Tomisue’s complaint, he “touched her body several times without her consent and despite her obvious reluctance.” Finally, Menard invited Tomisue to “join both him and his wife for sex after her husband went to bed” and told her if she refused, she would face “financial consequences.”

When Tomisue told Steve about the incident later that night, he shrugged off the advances, chalking them up to alcohol. But the following day, her complaint alleges, Menard approached her again. “If I do not get sexually what I want, there will be financial consequences,” she claims he said. “No one tells me ‘no.’”

John Menard and Steve Hilbert at the Brickyard 400 in Indianapolis

According to Tomisue’s court filings, Menard allegedly brought up sex with her repeatedly over the next couple of months in 2011 and insisted the Hilberts visit his home in Wisconsin, though Tomisue did her best to evade him. That July, the Hilberts watched Menard’s son Paul race in the Brickyard 400 from a suite at the Indianapolis Motor Speedway. That day, Tomisue declined an earlier request from Fay Menard for the Hilberts to visit them in Wisconsin. When Paul Menard won the race, the Hilberts joined the Menards in the winner’s circle to congratulate Paul.

According to a statement provided by Menard and his attorney, “Menard has never behaved inappropriately toward Mrs. Hilbert nor anyone else.” The Menard side has denied all of Tomisue Hilbert’s claims of misconduct in court filings as well, saying the “false and outrageous allegations” amounted to abuse of the legal process. The accusations were motivated by malice, according to Menard’s answer filed in response to Tomisue’s claim, and intended to embarrass Menard and gain some sort of “perceived advantage or leverage” in the Merchant Capital suit. Menard’s counterclaim points out that Tomisue brought her suit with those grievances nearly two years after the alleged sexual advances occurred, and only after the Hilberts became the target of the Merchant Capital suit. Asked about his relationship with Tomisue in a deposition tied to her lawsuit, Menard said that, in fact, “Tomisue always makes me uncomfortable.” For her part, Tomisue “vigorously denies Mr. Menard’s accusations,” says Jeffrey McDermott, her attorney, in a statement provided to IM.

The fallout spurred other lawsuits. After Tomisue’s friend Lisa Trudeau was dismissed from the company, Australian Gold sued her for $1.5 million—though she made a little more than $50,000 annually for five years—because she allegedly “did not provide the expected services of her employment” and ran up charges on the company credit card, according to court documents. “Upon being served with the summons and complaint” from Australian Gold, her countersuit alleges, “Trudeau, the then unemployed mother of four, fell to the ground in tears.”

Australian Gold has since withdrawn the claim for back salary but is still pursuing the claim that Trudeau misused a company credit card. “The total amount of the credit card charges in question is still being determined through the discovery process,” says Kevin Tyra, an attorney for Australian Gold.

Trudeau gave her attorneys photos, print ads, and Australian Gold catalog pages (including a shoot with a bikini-clad “Jwoww” from the reality series Jersey Shore), and turned over sequined pink handbags, gold lame drapes, sewing machines, a dress form, and other wardrobe, props, and makeup—items she purchased “with the credit card for business purposes,” according to a court filing. The evidence was “being stored by Mrs. Trudeau’s counsel for use at trial,” which, at press time, had no set date.

The matter of Tomisue Hilbert v. John Menard, meanwhile, is set for trial in April. The court has dismissed Tomisue’s claim that Menard committed a breach of fiduciary duty, and Tomisue dropped her claim against Menard for tortious interference with business relationships. But the lawsuit continues; the trial is set for early April. Lisa Trudeau, through an attorney, declined to comment for this story. Steve Hilbert retained a high-powered Chicago firm, Katten Muchin Rosenman, for his countersuit. Through his attorney, he declined to comment for this story as well.

Melania Trump’s part in the melodrama has concluded, at least for the time being. After the federal judge in Indianapolis ordered arbitration in her case with Merchant Capital and New Sunshine, “The matter was resolved to the mutual satisfaction of the parties,” says Alan Garten, executive vice president and general counsel at The Trump Organization. “That’s all I’m allowed to say.” Melania—now a First Lady of the United States hopeful—declined to comment.

The legal clash between Menard and Hilbert, the highest-stakes affair in the gamut of lawsuits that surrounds their falling-out, has no trial date and no conceivable ending. And the embattled Hilbert, once among the most envied and formidable businessmen in the country, is an unlikely underdog—a man who lost everything, got some of it back, and then lost that, too—now locked in a bloody war of attrition against Menard, a man with nearly unlimited resources. As of recently, Hilbert was still using his MH Private Equity email address—and it looks as though his means are dwindling, at least relative to Menard. A few years ago, he and Tomisue got yet another billionaire bailout, this time from Hilbert’s buddy Donald Trump, who, to help the couple with legal expenses, bought Le Chateau Des Palmiers in St. Martin, listed at $19.7 million.

But the Hilberts might be poised for yet another comeback: Last year, they swung a deal to buy—wait for it—a small insurance company.