Oscar Robertson Is the Reason NBA Players Sign Massive Contracts Today. Sadly, He Had To Auction All His Memorabilia To Stay Afloat

Last night at the ESPY Awards, NBA legend Oscar Robertson was honored with the Arthur Ashe Award for Courage. He now joins a hallowed list of recipients that includes Muhammad Ali, Billie Jean King, Pat Tillman, and Bill Russell. And frankly, no one deserves the recognition more than "The Big O."

Oscar was introduced for his award last night by Russell Westbrook. That's appropriate. In 2017, Russell broke Oscar's record for most triple-doubles in a season (41). That same year, Russell signed what was then the largest NBA contract in history, a 5-year, $205 million extension with Oklahoma that instantly propelled his salary from $15 million to over $40 million per year and put him on a path towards earning $350 million during his career. None of that would have been possible without Oscar.

Or take Shai Gilgeous-Alexander, who won Athlete of the Year at last night's ESPYs. In August 2021, after just TWO seasons in the NBA, Shai signed a 5-year, $170 million extension with Oklahoma City. Then, earlier this month, he signed a 4-year, $285 million extension. That latest extension will result in Shai making around $78 million for the 2030-2031 season.

None of today's mind-numbing NBA salaries and contracts would exist without Oscar Robertson. Oscar Robertson is the reason today's players make as much in a single season as Michael Jordan made during his entire career. He is the reason players are able to earn generational wealth from a single contract after spending just a few seasons in the NBA.

In fact, every NBA player from the last 30 years should be required to send Oscar a handwritten thank-you note the day they sign a mega contract. So should their children. Their grandchildren should send Oscar's grandchildren thank-you notes. And so on in perpetuity.

Oscar is the reason free agency exists. He risked his prime earning years—and his standing with owners—to change the power dynamic between players and the league forever.

And yet, in a cruel twist of fate, Oscar Robertson is also an example of someone who could have used the very security he fought to create. After a modestly paid Hall of Fame career and a decades-long battle to establish labor rights, he spent his later years grappling with financial hardship, eventually forced to auction off his championship ring, MVP trophy, and Hall of Fame memorabilia just to stay afloat.

(Photo by Michael Buckner/Variety via Getty Images)

The Early Years and NBA Career That Changed the Game

Oscar Robertson was born in 1938 in segregated Charlotte, Tennessee, and raised in poverty in Indianapolis. Too poor to afford a proper basketball, he learned the game using tennis balls and a homemade peach basket. His talent quickly outgrew those humble beginnings. At Crispus Attucks High School, he led the team to back-to-back Indiana state titles, making them the first all-Black school in the country to win a racially integrated championship.

He then starred at the University of Cincinnati, where he averaged 33.8 points per game and was named National College Player of the Year three times. He set over a dozen NCAA records, led his team to two Final Fours, and dealt with relentless racism on the road—banned from hotels in certain cities and forced to stay in dorms while his white teammates checked in.

In 1960, Robertson joined the Cincinnati Royals as a territorial pick and instantly became a force in the league. He was named Rookie of the Year, earned 12 All-Star selections, and won the league MVP in 1964. In the 1961–62 season, he became the first player in NBA history to average a triple-double—a milestone that stood unchallenged for decades. After being traded to the Milwaukee Bucks in 1970, he helped lead the team to its first NBA Championship alongside Kareem Abdul-Jabbar.

Despite his dominance, Robertson's earnings were modest by today's standards. His rookie deal paid $33,000—roughly $350,000 in today's dollars. At his peak, he earned around $100,000 to $250,000 per season. Over his entire 14-year career, Robertson earned a few million dollars in salary—barely enough to match the annual salary of a modern backup guard.

Excellent rewrite—this version is sharper, richer, and flows with great energy. Since you've removed the Shai mention from the body, I'll revise the follow-up sections accordingly and ensure Shai Gilgeous-Alexander is no longer referenced later in the article.

Here's the revised version of the full piece with your new opening, seamlessly followed by updated middle and closing sections:

The Early Years and NBA Career That Changed the Game

Oscar Robertson was born in 1938 in segregated Charlotte, Tennessee, and raised in poverty in Indianapolis. Too poor to afford a proper basketball, he learned the game using tennis balls and a homemade peach basket. His talent quickly outgrew those humble beginnings. At Crispus Attucks High School, he led the team to back-to-back Indiana state titles, making them the first all-Black school in the country to win a racially integrated championship.

He then starred at the University of Cincinnati, where he averaged 33.8 points per game and was named National College Player of the Year three times. He set over a dozen NCAA records, led his team to two Final Fours, and dealt with relentless racism on the road—banned from hotels in certain cities and forced to stay in dorms while his white teammates checked in.

In 1960, Robertson joined the Cincinnati Royals as a territorial pick and instantly became a force in the league. He was named Rookie of the Year, earned 12 All-Star selections, and won the league MVP in 1964. In the 1961–62 season, he became the first player in NBA history to average a triple-double—a milestone that stood unchallenged for decades. After being traded to the Milwaukee Bucks in 1970, he helped lead the team to its first NBA Championship alongside Kareem Abdul-Jabbar.

Despite his dominance, Robertson's earnings were modest by today's standards. His rookie deal paid $33,000—roughly $350,000 in today's dollars. At his peak, he earned around $100,000 to $250,000 per season. Over his entire 14-year career, Robertson earned a few million dollars in salary—barely enough to match the annual salary of a modern backup guard.

The Lawsuit That Transformed Professional Sports

In 1965, Robertson became president of the NBA Players Association and soon recognized how profoundly unfair the league's contract system was. At the time, players remained bound to their teams even after their contracts expired. The league's reserve clause—essentially a lifetime ownership model—meant that no player could choose where to work, negotiate freely, or test the open market.

When the NBA began planning a merger with the ABA in 1970, Robertson filed a historic antitrust lawsuit to block it. His goal was simple: force the league to dismantle its monopolistic control over player movement. The lawsuit would drag on for six years, delaying the merger and making Robertson a target among owners. Many players stayed silent or distanced themselves. Robertson refused to back down.

In 1976, the NBA finally settled, creating a new labor structure that introduced free agency and forever altered the economics of the league. The settlement became known as the "Oscar Robertson Rule." It gave players leverage for the first time, allowed them to negotiate with other teams, and laid the foundation for restricted and unrestricted free agency. MLB and NFL players would eventually follow the path Robertson carved out.

Today's NBA labor market—player empowerment, record-breaking contracts, and full control over one's career—can all be traced back to Robertson's fight. His legal battle didn't just change basketball. It changed professional sports.

Post-NBA Life, Business Collapse, and the Auction of a Legacy

After retiring in 1974, Robertson pivoted to business. In 1981, he founded Orchem, a Cincinnati-based specialty chemical company that produced industrial cleaning and sanitation products. His clients included national giants like Kraft, Pepsi, and Anheuser-Busch. At its height, Orchem was one of the largest minority-owned chemical companies in the U.S. It took years to turn a profit, but Robertson built it into a legitimate enterprise.

However, by the 1990s and 2000s, the company's financial position weakened. Orchem filed for bankruptcy in the mid-1990s, restructured, and continued to operate—but the debt kept piling up. By 2012, the company had defaulted on more than $2.4 million in loans, owed nearly $200,000 in back property taxes, and faced multiple tax liens and vendor lawsuits. Robertson, who had stepped away from daily operations to care for his ailing wife, was unaware of just how dire the situation had become until foreclosure proceedings were already underway.

To stave off bankruptcy, Oscar was forced to do the unthinkable: sell his most treasured possessions. His 1971 NBA Championship ring. His Hall of Fame ring and induction trophy. His 12 NBA All-Star rings. Even his 1964 MVP trophy. All of it was put up for auction in an attempt to cover mounting debts.

His title ring alone sold for more than $90,000. The MVP trophy fetched six figures. In total, the auction raised hundreds of thousands of dollars—but even that wasn't enough to fully wipe away what he owed.

Legacy

Oscar Robertson didn't just change the NBA — he changed the economics of sports. Every guaranteed max deal. Every bidding war in free agency. Every $250 million supermax contract. It all traces back to his willingness to stand up, speak out, and endure six years of legal warfare to tip the balance of power away from team owners and toward the players themselves. That fight cost him dearly, both professionally and financially. But it reshaped the lives of thousands of athletes who came after him.

Actually, I've rethought my suggestion that every NBA player should send Oscar a thank-you note. Here's a new plan:

Oscar never asked for anything in return for his sacrifice. Not then and not now. However. If you're an NBA player who has signed a contract worth more than $100 million, you should still send Oscar that thank-you note, but please also slip a couple of hundred-dollar bills in the envelope. Or, better yet, just Venmo him $1,000. And do it every year.

Because while he never cashed in on the riches he helped unlock, Oscar Robertson is the reason your children, and grandchildren, and great-grandchildren will never have to work.