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Miami booster John Ruiz’s NIL deals are controversial and aggressive, but he’s confident they are within rules and bring value to his businesses, athletes

By Bill King

John Ruiz stood amid family and colleagues on a stage at the Nasdaq stock exchange on a recent Wednesday morning, cheering raucously as the clock counted down to the opening bell.

 

A Miami graduate along with his three children, John Ruiz signed NIL deals with more than 100 Hurricanes players when rules changed.Courtesy of MSP Recovery

As confetti fell and the noise level rose, Ruiz raised his hands as high as his face, flashing both palms and touching his thumbs together, the unmistakable symbol of “The U” — the University of Miami.

On the day that he and his company MSP Recovery celebrated going public via the second largest SPAC merger in history, the newly minted billionaire felt a need to pay homage to his alma mater, where his two sons played baseball, his daughter graduated from law school and his zeal has him neck deep in a controversial quest to build a football stadium and a polarizing scheme to pay more than 100 UM athletes for the use of their name, image and likeness.

He caused the largest stir when he signed Nijel Pack, a Kansas State basketball player who transferred to Miami, to a two-year, $800,000 deal that includes the use of a car. In exchange, Pack will promote the MSP subsidiary LifeWallet, which collects and stores users’ medical records, and Ruiz’s Cigarette Racing powerboat company. Ruiz has scores of deals with lower profile UM athletes, who receive lesser sums to promote his brands.

His first 10 deals with UM football players totaled almost $400,000. He also signed Haley and Hanna Cavinder, basketball-playing twin sisters with large social media followings who transferred from Fresno State to UM. Ruiz said he has spent more than $5 million of a $10 million budget earmarked for NIL deals with Hurricanes players.

He is invested, emotionally and financially.

The John H. Ruiz File

Born: Miami Beach, 1967
Children: Johnny, Cristina, Alex
Education: University of Miami (1987); Nova Southeastern University Shepard Broad College of Law (1991)
TIMELINE
1992: Launches his own law practice
2002: Buys a television studio and airtime from GenTV to launch “La Ley con John H. Ruiz,” an informational legal program that runs until 2016.
2011: Signs a seven-year lease, with an option to buy for $16 million, at the 90-acre Homestead ballpark complex that had sat dormant since 1992, when the Cleveland Indians reneged on making the facility the team’s spring training home after Hurricane Andrew. He vacates the property in 2013.
2014: Founds Medicare Second Payer (MSP) Recovery, specializing in recovering payments from Medicare, Medicaid, commercial and secondary payers.
2016: Raises $350,000 in a seed-funding round for his proposed LifeWallet consumer app, which enables first responders and health care providers to access a person’s medical history before treatment.
May 2021: Acquires Cigarette Racing Team, a high-powered custom-made powerboats company (costs range from $600,000 to $3.5 million), along with Lionheart Capital.
July 2021: Announces a merger with Lionheart Acquisition Corporation II, a $230 million special purpose acquisition company, at a $32.6 billion valuation.
November 2021: Acquires Vectorworks, a marine engineering, tooling and manufacturing firm.
January 2022: Launches LifeWallet powered by MSP Recovery. The brand signs a $50,000 NIL deal with Miami’s Gil Frierson, the first of what has totaled 61 college athletes as of May 31. Ruiz also files a class-action lawsuit against the Florida High School Athletic Association to allow high school athletes to sign NIL deals.
April 2022: Announces that the 65,000-seat LifeWallet Stadium, designed by HKS, will be built for the Hurricanes football team at the city’s 270-acre 4 Tropical Park.
May 24, 2022: MSP Recovery goes public on the Nasdaq, opening at $5.24 per share. That had dropped 74% as of the close on May 31, to $1.36.
— David Broughton

So it was that when the Nasdaq bell rang, Ruiz celebrated as habit dictated, flashing a symbol dear to his heart.                     

“I doubt that has ever happened there before. Like, who does that?” said Ruiz, a son of Cuban immigrants who was raised near the dog track in Northwest Miami and has lived in Coral Gables for the past 30 years. “What was going through my head was what got me there. You have to go back to your origins. You can never forget where you came from and what got you to where you are. Ultimately, the University of Miami was my basis.

“It has been our lives.”

Ruiz enrolled in Miami as a 17-year-old freshman in 1984 and was instantly taken by the passion he encountered at UM football games at the Orange Bowl, where Jimmy Johnson was laying the foundation for an eventual national champion. He stayed close to home for law school, attending Nova Southeastern.

When the state froze an assistant district attorney’s job that he hoped to land, he instead hung out a shingle, renting an office in exchange for 20 hours of legal work a month. He practiced what he calls “door law,” taking any case or legal matter that walked through the door. He did his own research and filed his own pleadings, driving them to the courthouse himself.

He developed a reputation for good work, building a healthy practice. Only five years after graduating from law school in 1992, he landed his first big win, collecting about $10 million in fees from a $3.5 billion class-action settlement related to diet pills. Five years later, he doubled down on that success, increasing his profile across South Florida through a weekly Spanish language TV show that discussed everyday legal topics such as foreclosure and bankruptcy.

He also began to advertise the firm, which grew rapidly. His list of large, class-action settlements and wins mounted. It was while working on a case against a pharmaceutical company that Ruiz discovered a quirk in the Medicare insurance structure that often left the wrong parties paying for medical bills. Ruiz saw an opportunity to create a company that would identify those instances and recover that money.

The company now known as MSP Recovery says it uses proprietary analytics to identify the most lucrative claims, buy them from insurers at a discounted rate and collect from health care providers through litigation or settlements. The market has not responded well to the SPAC offering, with shares plunging from their $10 merger price to just above $1 last week.

Ruiz, who holds 65% of the company, explains the origin of his NIL strategy similarly to the way he described the root of MSP Recovery — an ability to use a combination of business and legal acumen to recognize gaps in a system and benefit from them, while careful to operate within the law.

John Ruiz didn’t forget his alma mater the day in May MSP Recovery went public on the NASDAQ.Courtesy of MSP Recovery

He said his idea for the first deals came to pass when MSP’s marketing department was considering an ad campaign for LifeWallet last year. He was floored by the cost: About $1.6 million for “a couple of weeks of billboards.” Aware that college athletes around the country had begun to benefit from their NIL rights, he asked his son, Alex, a recent grad who pitched at UM, if the school’s athletes would be willing to make some money promoting his product.

Alex Ruiz contacted Gilbert Frierson, a UM linebacker and classmate. Early in January, Frierson announced that he’d signed a one-year, $50,000 deal to promote Life Wallet. A couple of weeks later, Frierson appeared in his first online commercial spot, coached by Ruiz.

“It just took off and got a lot of attention,” Ruiz said. “From then I realized that not only was I doing something that had a good rate of return for the company — better than any other marketing tool — but I realized I was doing something really good for players. We were teaching these kids and they were having fun. And it just continued to grow from there.”

Skeptics and critics argue that Ruiz is overpaying a cadre of college athletes whose following is largely local or regional to promote a product that he says will be global. And that the exclusive use of Miami athletes in promotion of that product raises red flags.

With the help of his son Alex, Ruiz signed UM linebacker Gilbert Frierson to a $50,000 deal to promote LifeWallet.getty images

But Ruiz says impressions will bear out his investment, especially when considering differences in the amount he pays each athlete and what is required of them. At the high end, he points to the return from Pack, who Ruiz said delivered 6 million impressions from one tweet that announced he’d signed the largest NIL deal to date.

“I’ve continued to architect, making sure everything was done legally through NCAA rules, state rules and federal rules, and that this was providing a benefit not only to us but the players as well,” said Ruiz, who said the training and exposure to his businesses that players receive will benefit them more than the money. “And, honestly, the more money we put into it, the better result we’ve gotten.”

Ruiz also stresses that all his NIL deals have received the blessing of UM’s compliance department, which reviews all his contracts before they’re consummated. UM athletics representatives declined an interview request for this story. 

“I dot I’s and cross t’s — and I don’t get that from the university or the NCAA,” Ruiz said. “I create my own structures. That’s what I’ve done my whole life, doing massive litigation. I’m sort of a guy that is trained to go and find holes in people’s structures. So as the result of that, I play devil’s advocate with myself and my structure. What if I had a guy like John Ruiz on the other side? What would he be picking at? I go through that thought process and structure it so nobody can take it apart.

“It’s hard to poke holes in what we do because we do it legally.”

As an example, Ruiz points to limits he places on the players he works with. He won’t pay travel expenses for family members to come to a commercial shoot, acknowledging that it’s an impermissible benefit. And he says he’s a stickler on holding fast to the terms of an agreement, explaining to players that they are expected to continue to develop new social content and won’t be paid more than required by the original contract, even if they emerge as stars.

“I don’t know if there’s a single person who I’ve talked to on the booster or brand side who has as deep a desire [as Ruiz] to really dig deep into the rules and the laws and do his best to ensure compliance,” said Darren Heitner, a South Florida attorney who has worked on NIL deals for several athletes signed by Ruiz, including the Cavinder twins. “He’s not looking to put a target on his back despite his very vocal demeanor and tweets. He really does not want to put himself and, importantly, the athletes or the university, in jeopardy. He’s very cognizant and cautious. He cares a lot about the laws and is constantly doing diligence to make sure his contracts are not in violation of them.”

While many point to the current landscape as the “Wild, Wild West,” Ruiz disagrees. He said he believes the laws and rules are clear and that his structure adheres to them. He is less certain about others, such as some collectives and nonprofits that Ruiz says don’t clearly lay out what an athlete will do, or what they will promote, in exchange for an NIL payment.

“The reason I don’t like collectives or 501(c)(3)s — there is no quid pro quo,” Ruiz said. “That’s not business. My business has been around a long time, and I’ve been marketing my whole life. To me, what we do works perfectly.

“I didn’t just set this up for the purpose of getting money to players.”

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