In the early days of the pandemic, as the number of new COVID-19 cases in the United States climbed from a few hundred per day to a few thousand, Keith Middlebrook saw a business opportunity. He had previously downplayed the health crisis to his millions of social media followers, telling them to drink alkaline water and not listen to “the mainstream media” that “will talk you into failure.” But that was before he thought he could make a trillion and a half dollars by getting investors to believe he had what the whole world wanted: a vaccine.
On March 17, 2020, Middlebrook allegedly announced on Instagram that he had developed a pill that could prevent COVID-19 and an injectable serum that could cure it. He said he had tested the pill on someone and that it made the person “immune.” He posted more about it over the next several days, saying in one video while holding a syringe, “One injection of this, and the virus is dead in less than 72 hours.” These videos allegedly got more than a million and a half views.
Behind the scenes, Middlebrook was talking to a potential investor named Sean, whom he understood grew marijuana and had boatloads of cash. They agreed to meet in person; Sean would come down from Portland with the money, and Middlebrook would bring samples of the vaccine. Sean said he’d double his investment to $400,000 if Middlebrook met with him before going to another investor. “I’ll be there in 12 hours,” Sean told him.
On March 25, Middlebrook, who lives in Orange County, drove to El Segundo. He arrived by 6 o’clock, an hour before sunset. He and Sean spotted each other and had a brief exchange. Then FBI agents jumped out and apprehended Middlebrook. Sean had been an undercover agent.
“I got, I don’t know, at least 20 guns to my back and my head and my chest,” Middlebrook later told me during what appear to be his only interviews about the matter. In the crowd of feds, he spotted a familiar face. It belonged to the FBI agent who had arrested him years earlier on fraud charges in a case involving celebrities. According to more than a dozen interviews and lawsuits, the COVID-19 scheme was only Middlebrook’s latest and greatest con.
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Since the start of the pandemic, federal prosecutors have gone after hundreds of people over illegally trying to cash in on the crisis. Many are said to have sought loans they shouldn’t have. Others are accused of hoarding or price gouging personal protective equipment, or scamming the unemployed into bogus work-from-home gigs.
Then there are those accused of peddling fake medicine long before true vaccines became available. “In the beginning, cures were unheard of. We had no cure,” says Assistant U.S. Attorney Ranee Katzenstein, from the major frauds section at the U.S. Attorney’s office in Los Angeles, which is prosecuting Middlebrook’s case. Fraudsters took advantage. “We see, as circumstances change, individuals who will shamefully exploit the misfortunes of others adapt,” Katzenstein says. The FBI warned weeks into the pandemic: “One of the most lucrative schemes for criminals is offering you an opportunity to invest in a cure or treatment for the virus.”
Out of all the federal criminal cases to come out of COVID-19, Middlebrook’s was the very first. The 53-year-old has described himself as a “producer,” “writer,” “actor,” “real estate mogul,” “philanthropist,” “genius,” “super entrepreneur icon,” “businessman,” and “educational speaker.” He calls himself the “Real Iron Man,” a moniker he unsuccessfully tried to trademark. He’s listed more than 20 businesses he started, and his IMDB page has around the same number of film and TV appearances, almost all uncredited. He’s boasted about owning 19 properties, 11 cars, and 4 airplanes. He claimed to me to have a net worth of $20 million. Later, he said it was “in the billions.”
Middlebrook and I first spoke in May 2020, the day he was released on bond from L.A.’s Metropolitan Detention Center after his mother put up $150,000. “I’m with people that kill people, stab people…heroin addicts, drug addicts, meth addicts, cartel leaders, gang members, child molesters, and bank robbers,” he said of his stint in jail. “They’re not really focused on what I talk about: success, wealth, favor, abundance, God, goals, gratitude, giving, health, wellness, fitness, finance, business, real estate.”
But a deeper look at Middlebrook’s decades in Southern California reveals questionable claims and a trail of fraud allegations. Many of his companies are not registered. A private jet he bragged about owning had been sold for scrap years earlier. Former clients say they never interacted with anyone except him and maybe the occasional assistant or two, and never visited an office. Some of his supposed celebrity friends and clients deny knowing him. Other clients who do know him say they wish they didn’t. Trying to reach his supporters now is like flipping over a log and watching the insects scatter.
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Middlebrook was born in Honolulu, Hawaii, according to him. As he tells it, his father was in the military and his family moved a lot before putting down roots in Washington state. In the late 1980s, after high school and a brief stint as a bounty hunter, he moved to California and threw himself in motivational books by the likes of Tony Robbins and Donald Trump. He began working at fitness centers and then started two gyms of his own. But he lost the money he made in a nasty custody battle for his daughter and filed for bankruptcy in 1997. As he tried to recover, he figured out how to clean up his credit. At that point, he started a business fixing other people’s credit, eventually attracting celebrity clients.
Middlebrook started company after company, branching out from credit repair into entertainment, real estate, fitness, and law. On a website, he kept a list of his ventures: Keith Middlebrook Pro Sports Entertainment, Middlebrook Promotions, Middlebrook Productions, Elite Platinum Portfolios, Iron Man Industries, Koi Realty, and many, many more.
Some entities were more questionable than others. He sought charitable donations through the Keith Middlebrook Foundation, which was not a registered 501(c)(3). (He told donors to give directly to the charities he supported.) There also was the Law Offices of Keith Middlebrook, which advertised locations in La Jolla, Newport Beach, and Beverly Hills. He is not a lawyer (he never went to college) and instead calls himself a “legal consultant,” though California has no such category of authorized law-related service provider.
One supposed recipient of his legal services was Lindsay Lohan. Middlebrook has long said he helped with the actress’ highly publicized shoplifting case in 2011 and once escorted her to court. Photographs show them together outside the courthouse on one occasion. But Shawn Holley, Lohan’s lawyer at the time, says by email, “I don’t know Keith Middlebrook and don’t even remember ever hearing his name.” Lohan once told Gossip Cop something similar after Star called Middlebrook her “party pal”: “I met Keith Middlebrook once and then he started to stalk me.” Middlebrook insisted to Los Angeles that Lohan and Holley knew him.
Lohan would not be the only celebrity to distance herself. Former National Football League players Todd Wade and Obafemi Ayanbadejo deny writing the testimonials attributed to them on Middlebrook’s website. Ayanbadejo says Middlebrook helped with his credit but seemed to have ulterior motives. “He wanted to work with celebrities and athletes. That was his schtick. He wanted to be important,” Ayanbadejo says. “I think he was trying to game me and play me in a way almost like a spy would play an asset…. Everyone loves a good story, and he could tell a good story.” The former pro footballer points out that his apparent testimonial was dated 2000, which was the year he won the Super Bowl with the Baltimore Ravens, but around eight years before he hired Middlebrook. (Middlebrook stood by the testimonials, saying, “If they weren’t real and true, I wouldn’t put them up.”)
For non-famous folks, Middlebrook would do even less work, according to those people. They’ve alleged that Middlebrook would barrage them with celebrity photos to win their business and then take their money and run. When they’d check in, he’d make excuses and stall until they gave up, according to these people. The ordeals left them embarrassed or pissed off. “He really doesn’t know how close he’s gotten to getting really, really hurt,” says Jeff Little, who accused Middlebrook of running off with his $5,000 in the late 2000s. (Middlebrook disputed this claim and said he performed services for Little.)
Clients took him to court for allegedly ghosting them. In 2011, a man in Nevada sued him for breach of contract and fraud, claiming he paid Middlebrook $140,000 for credit services Middlebrook never performed. A judge dismissed the case when the man was unable to serve Middlebrook papers. (Middlebrook said the man lied and didn’t take his credit advice.) The same year, an attorney named Harrison Barnes sued Middlebrook and another man over contract fraud. “Keith apparently had this website where he was touting his ability to fix people’s credit and had all these pictures of stars and everything on it, so I ended up giving him all this money,” Barnes says. “Nothing happened. He just disappeared.” (Middlebrook said Barnes was lying, telling me, “I cleaned his credit perfect.”) Barnes filed a default judgment in the case and said he won. But Middlebrook said he won, though Barnes’s default judgment is the last docket entry. Both parties agree that Middlebrook hasn’t paid a dime.
In yet another court saga, a former client alleged that Middlebrook took her six-bedroom mansion in the Hamptons. According to federal and state lawsuits, Roberta Russo said a man named Robert Sacks had conned her into buying the house in 2007 so he could flip it and make her money. But Sacks turned out to be “a calculated, conniving, and manipulative con-artist who bilked the Russos out of millions of dollars,” she alleged in court. Sacks was a client of Middlebrook’s, Middlebrook told me. And in 2008, Sacks allegedly told Russo he had a buyer for the house: Middlebrook. Property and court records show Russo transferred the deed to Middlebrook in 2008. But she later claimed in court that she did so for free because she thought she would get her investment back from Sacks and never did. Middlebrook argued in court that Russo had hired him to “restore her financial portfolio” and had offered the deed when she couldn’t pay his fee.
Russo died in 2013 after allegedly losing millions of dollars to Sacks and the house to Middlebrook. Four months later, a judge rescinded and voided the 2008 deed because it was “induced by fraud.” But that didn’t stop Middlebrook from showing up in 2016 and offering the property manager “5,000 cash in a brown paper sack” to leave, according to a video the manager took. To Los Angeles, Middlebrook insisted he owns the property. But the local assessor’s office confirmed that Russo’s estate is the name on the deed. Sacks, meanwhile, was convicted in 2010 in an international bank fraud ring that tried to steal more than $30 million from customers.
Those disputes didn’t slow Middlebrook. And it seemed he no longer was content to just be around celebrities; he wanted to be one himself. “He was the most impressive credit repair [person] of anybody on the planet,” says Roderic Boling, an ex-convict and on-and-off associate of Middlebrook’s. “And he just decided one day that he didn’t want to be the guy behind everybody else…. He wanted to be the front guy.” So he started acting as an extra in film and TV, according to IMDB. His acting career peaked with a role in 2010’s Iron Man 2. As “expo cop,” he had three lines and was on screen for less than 30 seconds.
He tried to play celebrity offscreen, too. He posted photos and videos with fancy cars and private airplanes. He showed up to charity functions and movie premieres (Paul Blart: Mall Cop, You Don’t Mess with the Zohan), never missing an opportunity to pose in front of a step and repeat banner. Wherever he went, he’d grab photos with famous people and plaster them across his websites. And while the paparazzi usually chase celebrities, Middlebrook chased the paparazzi. As Boling put it, “He’s the perfect Hollywood paparazzi leech.”
But the flashy lifestyle and growing list of enemies would catch up with him. In a 2013 video, he said he had “cleaned the credits for the feds, the FBI.” And the FBI was watching.
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Raymond Pitesky was eating dinner with colleagues at the Luna Caprese restaurant in Islamabad, Pakistan, when everything around him exploded. The blast sent people and patio furniture flying, leaving behind an unrecognizable, bloody mess. The restaurant was popular among foreigners like Pitesky, and the Taliban had thrown a bomb onto its patio.
Pitesky was stationed there as an FBI agent. He had worked for the bureau his entire career since graduating from San Diego State almost two decades earlier. He survived the 2008 restaurant attack, and Robert Mueller, then the FBI director, awarded him a medal for his injuries. When pressed about the episode, Pitesky, the typical stoic G-man, would only tell people, “It doesn’t take courage to get blown up.”
By the early 2010s, Pitesky was back in the States and working as a special agent in California. That’s when Middlebrook’s name crossed his desk. Tipsters had made allegations about Middlebrook’s credit repair business. Pitesky began investigating and eventually discovered a person he thought might be willing to help: Boling, the on-and-off associate.
As Boling tells it, he met Middlebrook in the late 2000s through a mutual contact. Boling had a criminal past; he had pleaded guilty in 2007 to securities fraud after he helped leave hundreds of thousands of fraudulent stock tip messages on people’s voicemails. “I tend to be a white-collar-criminal-asshole magnet,” he says. The two of them hung out with yet another person who had faced charges: Pedro Benevides, a man reportedly known to the U.S. State Department as a “financial component” of Joaquin “El Chapo” Guzman’s Sinaloa Cartel. Benevides had been indicted on cocaine trafficking and money laundering charges in 2009, and the following year the feds seized from him and alleged associates tens of millions of dollars, luxury cars, and hundreds of gold bars. The government dropped the case due to unreliable witnesses. But in 2013, it announced new charges, this time in a $44 million bank fraud scheme.
That same year, Middlebrook obtained a Gulfstream jet from an LLC registered to Benevides’s wife, according to court and state records. The woman was about to file for divorce, and Middlebrook tricked her into drawing up the aircraft title transfer and giving him two cars, according to Boling and his ex-wife, Katie Cox, who says she heard it from Benevides’s wife, her friend. Benevides was so mad, that when Middlebrook came to Benevides’s home in Florida one day in 2014, Benevides took out a gun and brought Middlebrook to his barn and locked him in a stall with a donkey, according to Boling, who was there earlier that day and heard about what happened later, and Cox, who says she heard it from Benevides. A photo appears to show Middlebrook in the donkey stall.
Middlebrook disputed the claims. He said Benevides signed over the plane to him for credit work he did, and he bought the cars from the Benevides couple because they needed money. He also said Benevides did not pull a gun on him and only wanted to “show” him the barn and a donkey. Benevides later pleaded guilty in the bank fraud case and was sentenced to nine years in prison. As for the plane, which Middlebrook would claim as recently as December 2020 he still owned, it would be cut up and sold for scrap in 2016, according to an aircraft transaction company that a Federal Aviation Administration record indicates got it from Middlebrook. As the company understood it, the plane’s fuselage wound up as a movie prop in China.
With the Benevides dispute, Boling noticed a change in Middlebrook. “He went from being the guy who was the miracle guy that could fix your credit, to the guy that was…just literally taking people’s money, doing nothing,” Boling says. So when Pitesky from the FBI called, Boling was willing to talk.
Boling walked the government through his friend’s alleged credit repair scheme. By October 2014, the FBI had enough material to move on Middlebrook. The feds arrested him on 15 counts of mail fraud, 15 counts of aggravated identity theft, four counts of using a fraudulent government seal, and one count of bankruptcy fraud. The indictment alleged he had created fake documents claiming to be from businesses, government agencies, financial institutions, and creditors saying debts could be deleted, and that he sent them to credit reporting agencies. Those deletions would improve clients’ credit scores. He also allegedly forged government seals and client signatures and had sought “clients who were famous, wealthy, or otherwise high-profile.”
Middlebrook pleaded not guilty. “They lied and said that I defrauded celebrities and pro-athletes, when I did the exact opposite,” he told me. “I cleaned their credit to 800…and I educated them on credit and finance and business and real estate.” The case dragged on for two years. Then in 2016, the government filed to dismiss on a technicality: enough time had passed that the case likely violated the Speedy Trial Act.
Middlebrook declared victory. “He got his free get-out-of-jail free ticket. And instead of letting that scare the shit out of him,” Boling says, “he immediately jumped up on top of his race car like he had just won the Indy 500 and started giving the finger to the feds,” metaphorically. Middlebrook was free, but he would need a new way to make money.
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On March 9, 2020, Middlebrook filmed a video from the back of a Maybach he said cost $600,000. Dressed in a dark suit and shiny green tie, he spoke directly to the camera. “Don’t listen to the negative news and the negative media of the coronavirus,” he said. “Trump’s already got it nipped in the bud.” He invoked the title of one of Trump’s books: “Think like a billionaire.”
After the court dismissed his case in 2016, Middlebrook had pivoted. As he later told me, his credit repair business had dried up because the government shut down his companies. “There I was, trying to survive,” he said. “My main industry of credit scores, finance, and all that was shut down.” So he had started new businesses and tried to ride the Trump wave by painting himself a wildly successful businessman who could share his keys to success—for a price. No longer was he gossiping to Star; now he was tweeting at Trump (who retweeted him at least seven times) and doling out self-help advice. In 2017, he started Xccelerated Success, a seminar and consulting service that advertised a program on “power of goal setting, spiritual power of the universe, how to get anything you want, and much more.” Then in 2019 came Reverse Aging Technologies Inc., through which he said he created formulas to help with memory loss, energy, metabolism, muscle, sex drive, and other benefits.
So when COVID-19 hit, Middlebrook saw dollar signs. It seemed like the perfect opportunity to cash in on his pivot to self-help coach, despite his having downplayed the pandemic. Now he needed investors. But he made a mistake: he called Boling.
The two men had spoken since the 2014 case, and Middlebrook knew Boling had given information to the government. Middlebrook said Boling apologized; Boling says it was Middlebrook who reconciled. Either way, they were speaking again by mid-March, when Middlebrook pitched Boling his miracle products.
“I have a cure for COVID-19,” Middlebrook told him, according to Boling’s recollection.
“No you don’t,” Boling replied.
“Oh yeah I do,” Middlebrook said. They agreed to talk more and hung up. Middlebrook allegedly followed up with text messages saying his injection had cured a patient and that investors would get $200 to $300 million for putting in $1 million. Never mind saving humanity from the worst plague in a century; they would get filthy rich.
Practically before getting off the phone, Boling had started dialing Pitesky, the FBI agent. Boling knew the feds had never given up on investigating Middlebrook and were still looking into allegations that he defrauded a client out of $100,000. (The FBI declined to make Pitesky available for an interview.)
The feds got to work. If Middlebrook was running around injecting people, they needed to act fast. Meanwhile, Middlebrook allegedly contacted more potential investors, in Nevada, New York, Texas, and Colorado. Middlebrook told me he wrote an email and “shot it out to ten private friends.” A one-sheet he sent around listed a business entity behind the products and a list of directors and officers that included NBA veteran Earvin “Magic” Johnson. He also had Boling contact people, promising him a finder’s fee. That’s when Boling brought in “Sean,” the undercover agent. Middlebrook also was boasting on social media that he was talking to Dr. Robert Goldman, a member of the President’s Council on Sports, Fitness & Nutrition, part of the U.S. Department of Health and Human Services, and that he was headed to Mar-a-Lago for emergency U.S. Food and Drug Administration authorization from Trump.
But there would be no trip to Mar-a-Lago. Federal prosecutors charged him with fraud for allegedly seeking investments for products and a company that didn’t exist. As they alleged in the criminal complaint, Quantum Prevention CV Inc., the entity behind the products, appeared to have no corporate filing; a representative for Johnson said the basketball legend had no clue who Middlebrook was; and at the time there was no such thing as a COVID-19 cure or vaccine.
It’s unclear from the complaint if the FBI interviewed Goldman, from the President’s Council, a medical doctor whose website might have even more celebrity photos than Middlebrook’s. Middlebrook told me Goldman “interviewed” him for two hours and said, “We’ve got to get you in front of Trump.” But Goldman says there is “zero truth” about his offering help. “A friend of mine called me out of the blue and had this guy on the line and he sounded kind of crazy to me,” Goldman says by email. “I said, ‘If you want to do things like this, you really need to get the proper data and research done.’ The whole conversation was just a matter of a few minutes…. Frankly, he sounded like a nut.” (Middlebrook stood by his previous claims to me about Goldman.)
The government sees COVID-19 frauds as particularly cruel because they feed on fear. Katzenstein, from the U.S. Attorney’s office in L.A., says, “I think it’s unconscionable when people, whether through ego, arrogance, greed, or stupidity, victimize the public by preying on people’s desperations.”
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Middlebrook and I spoke more than two dozen times. He had an answer for everything. Why did Magic Johnson’s rep say the basketballer didn’t know him? Johnson had “to go into defense mode” when questioned, Middlebrook said. Middlebrook later suggested we “trap” Johnson by secretly recording him on a three-way call. (Johnson’s spokesperson did not respond to requests for comment.)
Why didn’t his company show up in corporate filings? First Middlebrook said he might have registered it as an “anonymous” entity, an option that hides certain ownership information. He sent me a BizFilings order confirmation. But BizFilings told me the order had been canceled due to lack of payment and never filed with the state. When I told Middlebrook, he blamed an incorrect fraud hold on his card and said he went to jail before he could fix the issue.
He still insisted his products worked. The immunity pill had 12 components and the vaccine had six, according to him. The ingredients were derived from green tea leaf extract, cocoa bean, coffee bean, the herb ma-huang, white willow bark, and other sources, he said. How did he create it when no one else at that time had been able to do so yet? “Because I think omniscient, I think limitless. I think on a different scale,” he said. To label him a con man is the “pathetic, horrible, negative thinking of losers,” he added. “How could I be a con man if all I do is help people?”
A week after that interview, he offered me $10,000 in cash to get him on Fox News. When I quickly declined, he said, “Cash is untraceable.” I declined again.
As his case has moved forward, Middlebrook hasn’t backed down, and neither has the government. In June 2020, a grand jury indicted him, raising the number of counts from one to 11, each with a maximum sentence of 20 years. Two weeks later, he pleaded not guilty. The trial was scheduled for late September, but on Monday, a federal judge agreed to push it to December to give Middlebrook’s attorney more time to go through 14,000 pages of discovery the government handed over. There are also the credit-work allegations unrelated to COVID-19 that the feds could still be pursuing. (The Middlebrook prosecutors could not comment on the ongoing case. Middlebrook’s lawyer did not respond to requests for comment.)
Does Middlebrook really believe everything he says? No, according to Boling, but Middlebrook thinks he’s a good enough salesman to make you believe it. “I got to give him credit,” Boling says. “He’s one of the boldest, brashest liars that I’ve ever seen in my life. He’ll stand there and adamantly explain to you that it’s nighttime while you’re standing in daylight with him. And he’ll explain to you why you’re not understanding it.”
Hours before deadline, a few allies came to Middlebrook’s defense, at his prodding. Alan Mandelberg says his longtime friend “believes what he believes. He’s sincere.… I don’t think he’s a charlatan.” Client Mark Bush says that regardless of Middlebrook’s claims outside of credit repair, “he successfully handled the business for me…. That’s what matters.” And Darris Love, a client who acted in The Secret World of Alex Mack in the ‘90s, says, “I’ve seen him do nothing but have integrity, and I’ve seen negative, nasty people turn on him.”
In late December, Middlebrook declined to comment on the case other than to tell me, “I’m going to win, win, win, and win,” and that he wouldn’t change his plea. He also said he now couldn’t talk about the pandemic, for which there finally were approved vaccines. But despite the comments about winning, he sounded more defeated than he had months earlier. He was no longer boasting about his connections to Floyd Mayweather and Paris Hilton. Out of his “thousands” of past clients, he couldn’t immediately name one who would vouch for him. “People turn into liars and deny,” he said. “They won’t even call me back.”
Middlebrook said everyone else is lying—the celebrities who denied knowing him, the government that charged him, the clients who sued him. According to him, he’s told the truth about everything, including his COVID-19 vaccine. Maybe Middlebrook is such a good salesman that he convinced even himself that what he says is true. “I’m 100 percent real in everything I do,” he said in one of our last conversations. “If I wasn’t, then I wouldn’t say it.” But, months earlier, he had shared with me another philosophy of his: “Perception is reality.”
Max Kutner has written for Newsweek, The Boston Globe, and Boston Magazine. He is the host and creator of the Audible podcast Radicalized.
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