In April 2022, a Fort Lauderdale company that customizes private aircraft for the wealthy invited media to the airport to tour its largest project to date, a Boeing 767 owned by Coral Gables attorney and entrepreneur John H. Ruiz. A 767 can carry a couple hundred people from Miami to Europe. VIP Completions outfitted Ruiz’s in “unparalleled luxury” to seat 33 and sleep 16. It had wool and silk carpeting, full stand-up showers, leather-lined cabinets, a dining table for seven, a separate conference room for eight and a master bedroom with a queen bed and Frette linens. Ruiz was on hand for the occasion. “This project is the realization of my dream to create a unique private aircraft for business, pleasure and family travel,” he said in a prepared statement.
Ruiz was realizing a lot of dreams. He had a successful law practice. He co-owned the iconic Cigarette Racing Team speedboat maker. He had achieved national prominence in sports by paying South Florida college athletes for endorsements. Within a year, thanks to him, the University of Miami women’s basketball team was in the Elite Eight and the men’s in the Final Four. He talked of building a stadium for Canes football.
Living Luxe
JOHN RUIZ, 57
- EDUCATION
BA (University of Miami), JD (Nova Southeastern University)
- BACKGROUND
A child of Cuban immigrants, Ruiz became an attorney noted for his work in class actions, mass torts, medical malpractice and product liability. He also sued the state over its citrus canker eradication program during the disease outbreak in the 1990s.
- NET WORTH
Estimated $1.5 billion in 2023, according to Forbes. “I’m a guy that started with an $800 credit card debt that my dad loaned me,” he once told media. “I worked super hard to make it to where I am.”
- ENTREPRENEURIAL ENDEAVORS
He founded the privately held MSP Recovery Law Firm and the publicly traded MSP Recovery, now known as LifeWallet, a company that seeks reimbursement for insurance claims paid by the wrong party. It also has a consumer health care app, LifeWallet.
- LITIGATION
Ruiz and his various companies are no stranger to the courtroom on their own account. His MSP has been sued by the software engineer who developed LifeWallet and by primary care company Cano Health. In 2011, the Florida Supreme Court issued him a public reprimand at the behest of the Florida Bar over his actions involving a lawsuit brought by a person who in 2003 fell at an apartment project he co-owned.
- BOATS, PLANES, HOMES, DONATIONS
Ruiz has said he’s been a boating enthusiast since his youth. He became a customer of speedboat maker Cigarette Racing Team in 2002 and in 2021 partnered to buy the private company. “I’m a fanatic of the brand,” he said. In 2022, he spent nearly $10 million remodeling his private Boeing 767, his fifth aircraft project following refurbishment of a Citation X, two Gulfstreams and a Sikorsky helicopter then in the works. The Miami Herald in 2023 reported that from 2018 to then, he and companies tied to him bought $150 million in properties, notably a nine-bedroom waterfront house in Coral Gables. Ruiz has given millions of dollars to his alma mater, UM, to Westminster Christian Academy, which his children attended, and other causes, including $1 million to victims of the Surfside condo tower collapse in 2021.
In his biggest dream of all, he had a deal pending to take a company he founded public at a valuation of $33 billion. He would be Florida’s richest person — quite a showing for the son of Cuban immigrants, the first in his family to go to college.
Born in Miami in 1967, Ruiz earned his bachelor’s from UM in 1987 and his law degree in 1991 from Nova Southeastern University in Davie in Broward County. He represented plaintiffs in personal injury cases, filed class action suits and mass torts and built a name on Spanish-language TV with his La Ley financial advice program. He acquired real estate and built businesses. At times, he encountered turbulence — “John ‘La Ley’ Ruiz Loses His Boat And Owes Money To Contractors” read the headline on a 2012 Miami New Times article — but his business trajectory trended upward.
In 2014, he and legal colleague Frank Quesada founded MSP Recovery to profit from the nation’s fragmented health care insurance marketplace. To understand how, start with an example: Someone on a Medicare Advantage plan gets hurt in a car wreck or slips and falls at a store. That person requires medical care — an ER visit, X-rays, physical therapy — and sues the other driver or store over the accident. All the health care providers ding the Medicare Advantage plan for payment while the suit is pending.
As a matter of public policy to keep the Medicare trust fund from going broke, Congress decades ago created the Medicare Secondary Payer Act. It takes 19 pages for a Congressional Research Service report to summarize the law and its regulations, but, in essence, Medicare expects any other insurance that an injured or ill person may have — employer group health plans, auto insurers, workers comp, the VA — to pay as the “primary” insurer when a beneficiary needs care in certain instances. Sometimes Medicare will front the costs for an injured person but, under the MSP law, it must be reimbursed by other insurers or the injured person if he or she wins a lawsuit or settlement. The secondary payer law reduced Medicare spending by $63 billion from 2015 through 2021, says the federal Centers for Medicare and Medicaid Services.
To ensure the correct party pays, federal law requires insurers to share data but, nonetheless, sometimes reimbursement doesn’t come through due to billing delays, legacy data systems, disagreements and victorious lawsuit winners who neglect to turn over the money to Medicare.
Medicare itself and Medicare Advantage plans, if they have to go to court to force payment, can collect double damages. Enter Ruiz and his MSP Recovery. “The original idea for MSP came over 10 years ago, while I was litigating large class action cases,” he told investors in 2021. “I came to the realization that health insurers were using the wrong laws to try to recover monies that were being lost at an alarming high rate through improper payments, and they also lacked the ability to identify those improper payments to begin with.”
Ruiz’s company found several paths to make money from the federal Medicare payer law. One approach: It acquired the rights to claims from insurers and health care providers, combed databases and went after reimbursement as an “assignee” — akin to a factoring company that buys businesses’ receivables and goes to collect. “What MSP Recovery has done is kicked it up a notch,” says Rafael Gonzalez, a partner with Cattie & Gonzalez in the Tampa area who works in the Medicare claims field. With 65 million Americans on Medicare, Gonzalez says, the recovery market represents “a lot of folks, a lot of claims, there is a lot of volume there.”
As he built MSP, Ruiz happened while buying some real estate to meet Miami investor Ophir Sternberg, founder of Lionheart Capital. Ruiz — a longtime boater who named one vessel “Class Action” — and Sternberg teamed in 2021 to buy Cigarette Racing. Ruiz’s son, Alex, became CEO, and Ruiz’s daughter, Cristina, became chief marketing officer.
Ruiz and Sternberg were just getting started. Sternberg utilized what are called special purpose acquisition companies — publicly traded corporate entities that early this decade came to the fore as a shortcut to taking private companies public. (Efforts to obtain an interview with Sternberg for this article weren’t successful.) Richard Branson’s space company Virgin Galactic went public through a SPAC, as did Orlando-based auto sensor company Luminar Technologies. A Sternberg SPAC in 2020 took public Fort Lauderdale-based BurgerFi International, parent of the burger brand and Anthony’s Coal Fired Pizza & Wings.
Overall, SPACs performed poorly. The Securities and Exchange Commission eventually tried to tamp down SPAC use, but not before July 2021 when Sternberg and Ruiz announced that a Sternberg SPAC would combine with Ruiz’s company in a deal valuing MSP at $33 billion, the second largest SPAC deal ever. Ruiz, with his 65% stake, on paper would be worth $21 billion.
Observers expressed skepticism. MSP had zero net revenue that year and lost $37 million. Forbes questioned how MSP could be valued that high before it saw claims through to settlement or the end of litigation. Forbes: “The new high watermark (sic) in financial alchemy using special purpose acquisition corporations, or SPACs, was unlocked this week with a deal that aims to conjure tens of billions of dollars almost entirely out of thin air.”
It took months for the deal to close. Ruiz in 2022 was paid $964,507, plus another $427,382 that represented money paid by his law firm and the value of life insurance and personal security that were provided to him. As the closing was hanging fire, Ruiz added to the business model. He acquired a consumer health tool called LifeWallet, announcing it in January 2022 as a way to let people store their health info for easy access for first responders and health care providers. He later wound up in litigation with LifeWallet’s creator but over time added new functions to LifeWallet and branded MSP as LifeWallet. MSP signed University of Miami football quarterback Tyler Van Dyke, two teammates and Canes golfer Morgan Pankow to endorsement deals.
In May 2022, after some financial maneuvering to push the deal over the finish line, MSP began trading on NASDAQ. The market promptly vaporized much of the company’s presumed value. Nonetheless, two days later Ruiz, Sternberg and MSP chief legal officer Quesada went to New York to ring the NASDAQ opening bell, surrounded by cheering employees and their families. Ruiz called it the “first day of a new chapter in MSP.”
More loss was to come. In March 2023, the company said it wouldn’t be able to file its 2022 annual report with the SEC on time. In April 2023, it said it would have to re-state its financials for the quarters ending in June and September 2022 to fix various financial reporting errors.
The SEC already was investigating and subpoenaing documents about the deal that took the company public and the financials that the company re-stated, the Miami Herald reported in a July 2023 article that uncovered the investigations’ existence. The article also revealed the U.S. Attorney’s Office in Miami subpoenaed info for a grand jury investigation.
The SEC and U.S. Attorney haven’t disclosed their concerns. The company told investors it was cooperating fully. It also said a company committee reviewed the matters that were the focus of the subpoenas and believed the investigation would be resolved without material consequence to the company, “however, there can be no assurance as to the outcome or future direction thereof.”
Law firms on behalf of investors filed class action suits or announced they were investigating filing similar suits — though several issued retractions after a couple months to their public relations releases announcing their moves. Ruiz’s company also is in litigation with LifeWallet’s founder from whom it acquired the name and LifeWallet assets. Cano Health, a South Florida primary care company with whom MSP did a recovery deal, sued and accused MSP of being a “sham.” MSP countersued. For a variety of reasons, Cano filed in bankruptcy court this year to reorganize.
MSP’s stock fell under $1 a share and NASDAQ threatened to delist it. In October, while trading at 7 cents a share, the company executed a 1-to-25 reverse stock split to shore up the price to meet the NASDAQ threshold, but it sank below $1 again by February before regaining some ground. It traded at 76 cents in March. Its valuation, judging by its market cap, was $168 million.
Back in 2021, when MSP and Lionheart were presenting the deal to investors, MSP projected a $632 million profit in 2023 on $963 million in revenue. As of early March, its full year numbers for 2023 weren’t out, but through the first nine months, it lost $609 million. Its recoveries from claims totaled $6.1 million over that time. In February, the company lost an 11th Circuit appeal that will hamper its ability to collect on Florida claims that don’t meet certain litigation prerequisites under Florida law.
Separately in February, the company noted that it lacked the resources to repay money coming due in the next year and warned of its ability to continue as a going concern within the year. Ruiz’s stake, as of mid-March, was valued at $85 million. Efforts to obtain an interview with Ruiz weren’t successful. He once told the media, “This isn’t a sprint. This is a marathon.”
NIL Dealmaker
With his multimillion-dollar investments in UM athletes, John Ruiz set the pace for a new era in college sports.
At the dawn of the new age of college athletes raking in endorsement dollars, businessman and University of Miami alum John Ruiz stood out. Ruiz told a sports media reporter with The Athletic in 2023 he had 160 to 165 athletes under contract for a total of $12 to $14 million in name, image and likeness deals. Among the notables: social media and basketball stars Haley and Hanna Cavinder, who arrived at UM in 2022 from Fresno State. The Cavinder twins led the women’s basketball team to the Elite Eight in 2023 while Nijel Pack took the men’s team to the Final Four. Pack reportedly had a two-year deal with a Ruiz company for $400,000 a year. Speedboat maker Cigarette Racing Team, which Ruiz co-owned, also made endorsement deals with UM stars, such as Canes quarterback Tyler Van Dyke.
“Ground zero for the endorsement revolution,” the New York Times said of the University of Miami.
Ruiz wanted the revolution to go further. On behalf of a Miami-Dade based Westminster Christian School baseball player, he sued the state high school athletic association to force it to allow high school players to make endorsement deals.
He also played a role in what was widely — if inaccurately — described as the first NCAA sanctions over NIL after he tweeted a picture of himself and the Cavinders at his home before they signed with UM. The sanction was for an impermissible contact between a booster and recruits, not an endorsement deal. Neither Ruiz nor the Cavinders were penalized. UM received a year of probation, a fine of $5,000 plus 1% of the women’s hoops budget and other sanctions. UM head coach Katie Meier, who recently retired, served a three-game suspension for setting up the meeting between Ruiz and the Cavinders.
What set Ruiz apart in the early NIL era was how quickly and publicly he staked out the space and that he delivered life-changing money. Ruiz’s actions convinced other business-people, more quietly, to make deals with athletes, says Darren Heitner, a Fort Lauderdale sports law attorney who helped draft Florida’s name, image and likeness law. Ruiz “made a massive impact. I think many positives came from it but many learning lessons. Overall, I would say it’s a net positive,” Heitner says. Heitner worked with the Cavinders, who ended their time at UM after the 2022-23 season.
Ruiz wasn’t alone in shelling out big dollars. But, says Amelia Island-based Kristi Dosh, founder of the Business of College Sports, “He was just the most transparent and vocal about it.” Efforts to obtain comment from the University of Miami were unsuccessful.
Meanwhile, the parameters of NIL remain very much in flux. The NCAA has investigated UF football following quarterback signee Jaden Rashada’s withdrawal from the team after the since-disbanded Gator Collective, a funding group, failed to deliver on a promised $13 million NIL deal. Rashada went to Arizona State. In January, the NCAA sanctioned Florida State after an assistant football coach took a potential transfer student and his parents to meet a booster who offered an NIL deal paying $15,000 a month. The unidentified player didn’t transfer.
But a month later, a federal judge in Tennessee blocked the NCAA’s ban on recruits signing endorsement deals with booster groups before joining programs. “It’s so rapidly evolving,” says Dosh.
At the collegiate level, though, Ruiz isn’t the presence he was. “He was always one of the first men thought of when NIL is mentioned,” Heitner says, “Today, when there’s a conversation about NIL, his name doesn’t really come up. Perhaps that’s intentional.”
Ruiz, however, looks to be vindicated on his view on high school athlete endorsements. The Florida High School Athletics Association has floated a plan to join 30 other states in allowing high school athletes to commercialize their name, image and likeness.