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Spend a few minutes on social media and you may notice a strange new genre of athlete interview: highly paid pros sitting down on podcasts to explain why earning tens of millions of dollars is not quite as lucrative as it sounds.

Maybe these clips are all surfacing at once by coincidence, or maybe older interviews are being chopped up and pushed back into the algorithm for easy engagement. Either way, the conversation has worn thin. Kyle Kuzma may have captured the backlash best with his recent post:

“Ngl it’s exhausting hearing athletes break down how their millions ‘aren’t really millions’ after taxes and fees. 40M after taxes is still 40M. The real issue isn’t the system, it’s lifestyle creep. Nobody told you to live like a king, buy 5 cars, or move with a 10‑person entourage. Modest is allowed.”

Odell Beckham Jr. may be the leading face of this trend. From the way these appearances circulate, it can feel like Beckham rarely sits for a podcast without walking through how a $100 million payday gets carved up by taxes, agents, lawyers, private jets, parties, casinos, girlfriends, vacations, mansions, jewelry and every other expense presented as unavoidable. By the end of the math, the fortune is framed as if it simply vanished.

Earlier today, Twitter was flooded with a clip of Sebastian Telfair arguing that $20 million in NBA earnings was not as much as people think. The day before, a C.J. McCollum video made the rounds in which he described how a $2 million NBA salary still left him feeling financially squeezed.

Then another McCollum clip began circulating. In this one, C.J. mentions an NBA player named “Pat,” saying he learned a great deal from him about business and long-term financial planning. McCollum described Pat’s operation this way:

“I learned a lot from Pat just in his approach. He has his own office, own business. I think he’s up to 15 employees. He’s doing really well, and his dad taught him a lot about real estate… Those steam room conversations, about business, structure, finance and long-term planning. He’s got like a half-a-billion dollar portfolio with his company. I know he’s doing really well.”

An NBA role player running a $500 million real estate portfolio??? Pat??? Who is CJ talking about? And what is going on???

A little bit of digging helped me identify the “Pat” CJ is referring to. It’s at Pat Connaughton, shooting guard for the Charlotte Hornets.

Since being drafted by the Portland Trail Blazers in 2015, Pat has made a little over $50 million in salary.

And it turns out McCollum was not exaggerating. If anything, he may have understated the number.

Connaughton recently told Boardroom that his company has a real estate portfolio valued at a little over $600 million. It has 19 employees, more than 1,200 residential units under construction, and completed $175 million worth of development in a single year. The company also raised $75 million from investors during that period.

Before anyone starts calling Pat the NBA’s newest secret billionaire, we need to explain what “$600 million real estate portfolio” actually means…

(Photo by Jacob Kupferman/Getty Images)

Pat Connaughton’s $600 Million Real Estate Side Hustle

Connaughton’s real estate career technically began before his NBA career.

In addition to playing basketball at Notre Dame, Pat was an elite baseball pitcher. The Baltimore Orioles selected him in the fourth round of the 2014 MLB Draft and paid him a signing bonus of approximately $428,000.

Instead of immediately blowing the money on a luxury car, Pat followed the advice of his father, Leonard, a longtime Boston-area contractor. They used part of the bonus to buy a house near Notre Dame, renovate the kitchen and bathrooms, and sell it after Pat’s senior year.

The project was not some massive home run. They invested approximately $150,000 and sold the house for around $180,000. But it taught Pat how to identify a property, manage renovations, and create equity.

Connaughton completed two more house flips during his first few years with the Portland Trail Blazers. He originally operated under the name Beach House LLC before rebranding the company as Three Leaf Development.

During those Portland years, Connaughton, McCollum, Damian Lillard, Ed Davis, Chris Kaman, and other teammates regularly discussed business and investing in the team’s steam room. McCollum eventually became Connaughton’s third outside real estate investor.

After Connaughton signed with the Milwaukee Bucks, he began raising money from more teammates, professional athletes, and business executives. He later combined his operation with the development arm of Matt Burow’s Catalyst Construction to form Three Leaf Partners.

Three Leaf Partners

Over time, Three Leaf graduated from flipping houses to developing large apartment communities, mixed-use properties, and industrial buildings. It now has approximately 240 investors, including 62 athletes from the NBA, NFL, MLB and NHL. And, if Pat’s statements are true, they now manage $600 million worth of real estate.  But what does that mean for Pat Connaughton’s net worth?

The $600 million number represents the gross value of the developments controlled, built, or managed by Three Leaf Partners. It includes properties financed with construction loans, mortgages, and money supplied by hundreds of outside investors.

Let’s Do Some Napkin Math

Three Leaf is privately held, so its debts, investor contributions, ownership percentages, and profits are not publicly available. But we can use standard commercial real estate assumptions to illustrate what might be happening beneath the $600 million headline. Follow the text I’ve bolded and made red below:

Commercial real estate projects typically use bank debt equal to around 65% to 75% of their total value. Let’s assume Three Leaf’s portfolio is financed at a 70% loan-to-value ratio:

  • Gross portfolio value: $600 million
  • Estimated mortgages and construction debt: $420 million
  • Remaining equity: $180 million

That $180 million of equity would still not belong entirely to Three Leaf. The company has approximately 240 investors and has raised tens of millions of dollars from athletes, executives, and other outside limited partners.

Let’s assume those outside investors supplied 85% of the equity:

  • Outside investors’ share: $153 million
  • Three Leaf and its internal partners’ share: $27 million

Even that remaining $27 million would not belong entirely to Connaughton. It would be divided among Pat, Matt Burow, the company, and potentially other internal partners.

But Pat’s upside goes well beyond his portion of that $27 million.

How Much Could Connaughton’s Stake Be Worth?

Let’s assume Connaughton personally invested approximately $8 million of his NBA earnings into Three Leaf projects. As those developments were completed, leased, and stabilized, that equity may have appreciated to approximately $11 million.

Three Leaf also earns a general partner promote. In a typical arrangement, outside investors receive their original capital and an agreed-upon minimum return. The general partner then receives an enhanced percentage of the remaining profits. Connaughton’s accumulated share of those profits could plausibly be worth another $5 million.

Finally, Three Leaf Partners has value as a standalone company.

Three Leaf has 19 employees, an executive team, hundreds of investor relationships, and a pipeline capable of producing $175 million worth of development in one year. It earns fees for developing, financing, and managing projects even before the properties are eventually sold or refinanced.

A company operating at that scale could conceivably be worth $15 million to $25 million. If Connaughton owns a controlling stake of around 60%, his ownership interest might be worth approximately $12 million.

Here is our rough estimate of Pat’s real estate wealth:

  • Direct equity in Three Leaf projects: $11 million
  • Accumulated promote and development profits: $5 million
  • Value of his Three Leaf Partners ownership: $12 million
  • Total estimated real estate-related wealth: $28 million

Again, these are not disclosed numbers. We do not know how much money Connaughton has personally invested, exactly what percentage of Three Leaf he owns, or how much carried interest he has earned. The math above is simply an attempt to translate a $600 million gross portfolio into a reasonable estimate of Pat’s personal equity.

The Other Side of Real Estate Leverage

Pat Connaughton is not the first pro athlete to play the real estate game. And this game can get ugly on a dime with a slight change in interest rates or a downturn in the economy.

Former NBA star Antoine Walker also built a real estate investment company as a side business. According to Walker, he did not initially have to contribute much cash because he personally guaranteed the loans with his investment portfolio. The arrangement worked while property values were rising and the banks were happy to lend.

Then the 2007–2008 real estate market collapsed.

Properties lost value, loans defaulted and the banks came after Walker personally. He has estimated that he lost around $18 million in real estate. In 2010, after earning more than $100 million during his NBA career, Walker filed for bankruptcy with approximately $12.7 million in liabilities and $4.3 million in assets. His lavish spending and gambling also contributed to his downfall, but the real estate guarantees turned a struggling business into a personal financial disaster.

To be clear, there is no evidence that Connaughton has personally guaranteed Three Leaf’s debts or that the company is experiencing financial trouble. We also do not know whether its loans carry fixed or floating interest rates, when they mature or how much cash flow its completed properties generate.

But leverage cuts both ways.

Using our hypothetical numbers, a $600 million portfolio financed with 70% debt would carry approximately $420 million in loans. If those loans have variable rates, interest expenses could rise sharply. If they mature during a difficult credit market, Three Leaf might have to refinance at much higher rates. At the same time, falling rents, rising vacancies, construction delays or declining property values could reduce the income and collateral supporting those loans.

Suddenly, the same leverage that allowed a relatively small amount of equity to control $600 million of real estate could begin working in reverse.

For now, Connaughton’s operation appears to be an extraordinary success. And we hope it stays that way!

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