From the NBA Bench to Business Moguls: Role Players Who Built Financial Empires Off the Court

Welcome to Buckets and Riches — where NBA stars don’t just shoot threes, they stack Gs. From tunnel fits worth mortgages to endorsement empires and crypto hiccups, we break down how basketball’s elite earn it, flex it, and sometimes… brick it. 🏀💸

The latest edition of our newsletter covers:

• Buckets, Burgers, Then Billions

• Pistons Legend Powers Piston Group

• Wine, Media, and Winning Moves

• Building Wealth Brick by Brick

💸Money Machine

Junior Bridgeman: A Masterclass in Business

These days, being an NBA role player is one of the most lucrative forms of employment out there. Coming off the bench may not get you in the ballpark of the four-year, $285 million supermax extension that Shai Gilgeous-Alexander just signed. But for players like Santi Aldama and Duncan Robinson, who recently signed three-year deals in the $50 million range, it’s good work if you can get it.

NBA contract figures have risen exponentially in recent years. Players back in the 1970s and ’80s earned peanuts compared to current players. Today’s minimum salary is over $1.1 million. Compare that to the landmark $1 million per year (25-year, $25 million) deal that Magic Johnson signed in 1981.

Even the game’s biggest stars from back then didn’t make much. Role players made even less. Junior Bridgeman was one such player, a sixth-man extraordinaire who averaged nearly 14 points per game. 

Bridgeman played 10 years with the Milwaukee Bucks after the Lakers drafted him and traded him there as part of the Kareem Abdul-Jabbar deal in 1975. He later got to play in L.A. when he joined the Clippers for two years near the end of his career.

Bridgeman played for some excellent Bucks teams under head coach Don Nelson. And, although he never quite hit the highs of teammates Sidney Moncrief or Marques Johnson, Bridgeman was a hugely important part of a team that reached back-to-back conference finals in 1983 and 1984.

In his 12 years in the league, Bridgeman made just under $3 million in total. For some perspective, SGA will make that much in the first week of the season. However, unlike many retired athletes who fall on hard times, Bridgeman built a business empire.

Bridgeman learned the ropes of the fast-food industry, eventually investing in several Wendy’s franchises in the Milwaukee area. When those proved profitable, he bought more and expanded to the rest of Wisconsin and beyond. 

He then invested in Chili’s restaurants under his Bridgeman Foods business, which, at its peak, owned and operated more than 450 fast-food restaurants.

In 2016, Bridgeman sold many of his restaurants to become an independent Coca-Cola bottler and a minority owner of the Bucks. In February of this year, Forbes estimated his net worth at $1.4 billion. 

Sadly, Bridgeman passed away from a heart attack just under a month after that article was published. But he left behind a legacy and a blueprint that all former athletes would be wise to follow. NBA salaries may have changed, but the lessons from Bridgeman’s masterclass in business still ring true.

💸 Moneyball Moments

Luol Deng quietly built a real estate portfolio worth over $125 million after retiring, making him one of the most successful post-NBA investors, with properties spanning hotels, resorts, and commercial developments across the U.S., U.K., and Africa.

💰Sip and Swish

Uncorking a Business Legacy: How CJ McCollum’s Wine Play Is Aging Like Fine Merlot

CJ McCollum, one of the most consistent NBA scorers of the past decade, is a savvy businessman to boot. The Wizards guard has followed the age-old advice of not keeping all his eggs in one basket when it comes to investment.

If McCollum were to retire today, he would have earned more money from his 12-year NBA career than many people will ever see: $248.8 million. That puts the 6-foot-3 veteran 35th on the list of highest career earners of all time.

Many believe that it is more than enough money to stay afloat. McCollum may agree, but he doesn’t want his family worrying about finances ever again. To secure his fortune, he has invested in multiple businesses, the most noteworthy being in the wine industry.

McCollum has always had a deep love for sparkling wine. During the height of the COVID-19 Pandemic, he pursued this passion and acquired a 318-acre parcel of land in Portland, Oregon, becoming the first NBA player to purchase a vineyard. 

In 2020, the Wizards star founded McCollum Heritage 91, which is a tribute to his birth year, 1991. The Oregon vineyard is where McCollum Heritage 91 is produced and bottled.

Each bottle retails for $50. But for McCollum, this is not just about money. He has his eyes set on creating a brand that brings people together through wine.

🏀 Courtside to Construction Sites

Pat Connaughton: 3-Point Shooter Turned Real Estate Mogul

Pat Connaughton has made a name for himself as a serviceable role player in the NBA. But his business portfolio far exceeds basketball. 

The one-time NBA champion understands that basketball will only fill a brief portion of his life, so he has made sure to establish a stream of income outside of the sport. And Connaughton found his niche in real estate. 

His experience with flipping homes began during his time as a student-athlete at Notre Dame. He never let go of that passion and developed it into the real estate firm, Three Leaf Partners. 

Connaughton isn’t a superstar in the league, which means his contracts are on the smaller scale. After 10 years in the NBA, the former 41st overall pick in the 2015 NBA Draft has career earnings of $41.6 million. He has likely saved a good chunk of that money.

But Connaughton’s work with Three Leaf Partners ensures he won’t have to worry about money later in life. This past year was a successful one for his real estate firm. They completed 10 projects at a combined value of $195 million in 2024. Their total portfolio valuation is at a whopping $550 million. 

Many other wealthy people have taken notice of Connaughton’s group. The firm has a total of 236 investors, 40 of whom are professional athletes. 

Connaughton has gone down a unique path, which showcases that basketball doesn’t have to be a player’s main source of income. In the unfortunate case that his career comes to a premature end, finances won’t be a problem. 

📚Also Worth Reading

• "My Movie Theatres Were Crushing It": Magic Johnson Reveals How He Convinced $3.3 Billion Worth Founder to Do Business Together

• “I Never Think About Money”: When Shaquille O’Neal Revealed the Thought Process Behind His Business Decisions

• Jimmy Butler Described What Drove Him to Join the Competitive $223.78B Coffee Business