Stephen A. Smith vs. Isiah Thomas:
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From CBA Collapse to $100 Million Comeback
Stephen A. Smith never pulls his punches. But this time, he wasn’t just criticizing a bad coaching decision or a rough playoff series. He was going straight at a Hall of Famer’s legacy.
And in his crosshairs?
Isiah Thomas.
On air, Stephen A. dropped a bomb.
“It’s so bad right now… if you believe what I’m hearing, Isiah might as well be scouting the nearest homeless shelter.”
Harsh words. But in Stephen A.’s mind, this wasn’t about a single mistake. This was the culmination of years of mismanagement, scandals, and failed experiments—stretching all the way back to one of the most bizarre business disasters in basketball history:
the fall of the Continental Basketball Association.
The CBA: From “League of Dreams” to Bankruptcy
In 1999, Isiah Thomas, already an NBA legend, made a bold move. He bought the 55‑year‑old Continental Basketball Association (CBA) for around $9–10 million. On paper, it sounded like the perfect play.
The pitch was dazzling:
He promised NBA partnerships.
He talked about national TV deals.
He teased expansion beyond 20 teams.
Owners were hooked. This wasn’t just any investor. This was Isiah Thomas—two-time NBA champion, Pistons icon, business visionary.
Former CBA commissioner Gary Hunter remembered the buzz. There was real optimism. But that hope didn’t last long.
From day one, chaos followed.
On the very first day of ownership, Isiah did something that shocked everyone: he fired every head coach in the league.
Former Rockford Lightning coach Bruce Deelio recalled:
“The next day after the purchase announcement, he comes out to the press and fires every head coach in the league. It was chaos.”
These weren’t disposable assistants. Many of those coaches had helped make the CBA the NBA’s top development league for decades.
Then came the cuts.
Player salaries were slashed from around $1,500 per week to $1,100.
The talent pipeline—the very thing that made the CBA valuable—began to dry up.
The big TV deals he pitched?
Never arrived.
The national sponsors?
Didn’t show.
The NBA cross-promotions?
Didn’t materialize.
Instead, the league bled money. Teams missed payroll. Players went unpaid for months. Lawsuits piled up. The CBA—once a 55‑year institution—was spiraling.
And then came the decision that, to Stephen A., defined the whole disaster.
The $11 Million Offer… and the Ego Play
At one point, the NBA stepped in with a lifeline.
The league offered Isiah $11 million plus a share of profits to acquire the CBA and use it as the foundation for a new developmental league.
It was a way out, a way to protect the players, the teams, and the legacy of the CBA.
But Isiah wanted more.
He demanded $15–20 million.
The NBA walked.
Instead of buying the CBA, the league launched its own developmental system: the NBDL (now the G League). They cut their $2 million annual subsidy to the CBA, and just like that, the old league lost its biggest partner and financial anchor.
Stephen A. would later go off on his podcast, unleashing a furious rant about that moment:
“Thomas swoops in like a savior—‘League of Dreams,’ he calls it.
18 months later? Bankruptcy.
He cuts salaries, axes the coaches who built the thing, rejects Stern’s lifeline because 11 mil wasn’t enough for his flip.
Blind trust—that’s code for ‘I’m out, good luck.’
He bankrupted a 55‑year institution. Players bouncing checks. Owners in court.
If that’s not failure, what is?”
The Blind Trust and the Death of a League
The final blow came when Isiah accepted the Indiana Pacers’ head coaching job in October 2000.
NBA rules meant he had to place the CBA in a blind trust. On paper, it sounded like a technicality. In reality, it was devastating. Operational control vanished. No one had clear authority to fix the mess or make urgent financial decisions.
As bills piled up and teams defaulted on obligations, the league drifted toward collapse.
In February 2001, the CBA filed for Chapter 7 bankruptcy.
More than $300,000 in unpaid debts remained. The La Crosse Bobcats alone claimed Isiah owed them $300,000 in guarantees.
A 55‑year league, once the NBA’s official farm system, was gone.
Isiah moved on. The CBA never recovered.
Stephen A. never let it go.
The Knicks Era: Dysfunction on the Biggest Stage
If the CBA story was the first chapter of Isiah’s executive downfall, the New York Knicks were the sequel—and this time, it was on the biggest stage in basketball.
From 2003 to 2008, Isiah ran the Knicks, first as president of basketball operations, then as head coach.
The results were brutal:
Record: 96–140
Highest payroll in the league
Little to show for it but frustration and embarrassment
As a die-hard Knicks fan, Stephen A. took it personally.
“Every time I look at the New York Knicks, y’all running around organizationally—
not the players, I’m talking about management—
like a bunch of wusses, scared of your own damn shadow.”
Isiah’s moves became infamous:
$77 million for Stephon Marbury, a ball-dominant guard who clashed with teammates and coaches.
$60 million for Eddy Curry, with a no-trade clause.
$30 million for Jerome James—after one decent playoff run. James would play just 44 games for the Knicks, averaging 3.3 points.
By 2010, the Knicks had paid around $183 million in luxury tax penalties, much of it tied to contracts signed under Isiah’s watch.
Then came the Larry Brown fiasco—another symbol of chaos.
Isiah brought in the Hall of Fame coach on a five-year, $40 million deal in 2005. But Brown and Marbury clashed instantly. The roster didn’t fit the coach’s philosophy. After a 23–59 season, Brown was fired. The Knicks tried to withhold his remaining salary, sparking yet another expensive legal fight.
Years later, in his 2023 memoir, Stephen A. didn’t hold back:
“Isiah’s Knicks era was disgusting. As a fan, it wounded me.
He bankrupted the spirit of the franchise with ego trades and scandals.”
And then came the scandal that broke out of the basketball bubble and into national headlines.
The Harassment Scandal: Madison Square Garden on Trial
The Ana Sanders Brown lawsuit wasn’t just another sports controversy. It was one of the most damaging harassment cases in NBA history.
Sanders, a senior VP of marketing for the Knicks, accused Isiah and Madison Square Garden of creating a hostile work environment. The trial lasted three weeks and turned MSG into a public spectacle.
Testimony described:
Profane outbursts by Isiah
Alleged degrading language and unwanted advances
A toxic, “Animal House in sneakers” culture
Stephon Marbury admitted under oath that he called Sanders a racist slur.
Isiah testified that such language was less offensive among Black colleagues—a remark that triggered a firestorm of criticism.
The jury awarded Sanders $11.6 million in damages. MSG later settled for $11.5 million, while Isiah walked away with a reported $12 million severance despite being fired for cause.
The damage wasn’t just financial. The Knicks were already one of the worst teams in the league. Now, their reputation off the court was just as bad.
“Fire Isiah” chants echoed through Madison Square Garden.
David Stern called it a PR nightmare for the NBA.
Fans organized boycotts. Season ticket holders demanded refunds.
Isiah’s name was now tied not just to failed trades and bloated contracts, but to moral and cultural failure.
To Stephen A., this was proof: some people just weren’t built for positions of power.
FIU, NCAA Violations, and More Controversy
Isiah’s next chapter was supposed to be a reset.
In 2009, he took over as head coach at Florida International University (FIU), signing a five-year, $1.29 million deal.
But instead of a quiet rebuilding project, controversy followed him.
Record: 26–72
NCAA violations for impermissible phone calls to recruits
A bizarre conflict of interest when he secretly took a consulting job with the Knicks while still coaching FIU
When the dual role became public, the backlash was swift. FIU officials were blindsided. The NCAA took notice. Public pressure forced Isiah to walk away from the Knicks consultant job within weeks.
By 2012, FIU fired him. Players walked out in protest, calling him a father figure. But the program was left with sanctions, forfeited wins, and a damaged reputation.
Once again, Isiah moved on. Once again, the organization he left behind had to pick up the pieces.
A Feud That Won’t Die: Stephen A. vs. Isiah
Over the years, the tension between Stephen A. Smith and Isiah Thomas evolved from criticism into a full-blown rivalry—one that played out across TV, podcasts, and social media.
In May 2024, the feud resurfaced over Celtics star Jaylen Brown.
On First Take, Stephen A. questioned Brown’s marketability, citing an anonymous NBA source who claimed Brown’s “I’m better than you” attitude hurt his appeal—even as Brown was in the middle of a dominant playoff run and had just signed a record contract.
Isiah, who has mentored Brown since his days at UC Berkeley, fired back on X:
“I have been a friend, mentor, and adviser to Jaylen Brown since he was a student at UC Berkeley.
He is 100% marketable.
Before you slander his name, Stephen A. Smith, tell your source to put their name on it or don’t speak on it. Let it be known.”
Stephen A. responded with classic Stephen A. energy:
“I have no idea what you’re talking about, Isiah Thomas. I’ve been a fan of Jaylen Brown for years. Still am.
What’s unfortunate is that you—who’s known me for decades—would choose to go on X instead of calling me directly. But I get it. Do your job. I’ll do mine.”
Jaylen Brown himself jumped in, posting the First Take clip with the caption:
“State your source.”
He later wore a “State Your Source” T-shirt during the Celtics’ 2024 Championship parade, turning the moment into a cultural statement.
For Stephen A. and Isiah, it was another public flashpoint in a long, messy history.
The Shadow of Michael Jordan and the Dream Team
Beneath all of these battles—CBA, Knicks, harassment scandal, FIU—there’s a deeper wound that never really healed: Isiah Thomas’s feud with Michael Jordan.
The 2020 documentary The Last Dance reignited it all.
The film portrayed the Detroit Pistons as villains—the Bad Boys who tried to beat Jordan into submission. It revisited the infamous 1991 Eastern Conference Finals, when the Pistons walked off without shaking hands after being swept by the Bulls.
The documentary also highlighted something that had long been rumored:
Jordan told Olympic officials he wouldn’t play on the 1992 Dream Team if Isiah was on the roster.
Isiah was painted as a bitter, controversial figure. For him, it wasn’t just about a team. It was about his name, his legacy, his character.
In 2024, Isiah went on The Draymond Green Show with a simple demand for Jordan:
“You got on national television and you called me an *** and said you hated me.
If you didn’t mean it—get on national television and say that, and apologize for it.
If you meant it, let it ride as is.”
Stephen A.’s response?
“Michael Jordan doesn’t give a damn.
He doesn’t care if he ever speaks to Isiah Thomas again in life.
He’s not fond of him. Period.”
To Stephen A., Isiah’s pain was real—but so were the consequences of his own actions over the years. The Dream Team snub, the Pistons’ walk-off, the Bad Boys’ tactics—all of it fed into a narrative that Isiah has spent decades trying to rewrite.
From Chicago Streets to $100 Million
Here’s the twist that makes Isiah Thomas’s story so complicated:
For all the scandals, failures, and feuds, his life is also one of the most remarkable success stories in sports history.
Born on April 30, 1961, on Chicago’s West Side, Isiah was the youngest of nine children. His father, a war veteran and the first Black supervisor at International Harvester, left the family when Isiah was just three.
His mother, Mary Thomas, was left to raise nine kids alone in a cramped, unheated three-bedroom home. The kids slept on floors and ironing boards. They often didn’t know where the next meal was coming from.
Isiah remembers scavenging for food from fast-food wrappers and searching for loose change in the streets.
Basketball saved him.
At St. Joseph High School, he became a star, averaging 28 points and 12 assists as a junior. At Indiana University, under the famously intense Bob Knight, he sharpened his game and his mind. He later earned a degree in criminal justice and even went on to get a master’s in education from UC Berkeley in 2013, focusing on Black athletes and access to higher education.
On the court, he became a legend:
13-year NBA career with the Detroit Pistons
Two championships (1989, 1990)
12 All-Star selections
19.2 points and 9.3 assists per game over 979 games
Finals MVP in 1990
He helped engineer the “Jordan Rules,” a defensive blueprint designed to slow down Michael Jordan. He turned Detroit into the “Bad Boys” dynasty and led one of the toughest teams in history.
Off the court, despite all the public failures, he quietly built something else:
a business empire.
The Comeback: Isiah the Businessman
Today, Isiah Thomas is estimated to be worth around $100 million. Not because of his playing salary—he made just $6.7 million in NBA earnings—but because of the empire he built afterward.
Through Isaiah International LLC, his holding company founded in 1990, he controls a diversified portfolio:
Real Estate
Isaiah Real Estate is developing a $300 million mixed-use complex in Chicago’s Illinois Medical District, including housing, medical facilities, and commercial space aimed at serving the community he once came from.
Environmental Services
He co-owns GRRE3 In-Waste Removal and RE3 Recycling with his daughter Lauren, riding the wave of demand for sustainable waste management in urban markets.
Cannabis
As CEO of One World Pharma, Isiah is deeply involved in the booming cannabis industry, focusing on equity, inclusion, and ensuring that communities harmed by old drug laws can benefit from legalization.
Luxury Goods
He’s the exclusive U.S. importer of Cheurlin Champagne, which became the NBA’s official bubbly in 2016. He’s blended European luxury with basketball culture, building a brand that appears at major political and sports events.
Annual earnings from these ventures reportedly reach around $20 million.
By 2025, Isiah wasn’t a broke ex-player. He was a diversified, high-level entrepreneur—exactly the kind of post-career success story most athletes dream of.
The man Stephen A. once roasted as a failed executive was now thriving in business.
Still in the Game: Coaching, Media, and Mentorship
Basketball never left his life.
Isiah was named head coach of the Saginaw Soul in the Basketball Super League for the 2025–26 season, focusing on player development in a growing minor league system. Unlike his Knicks or Pacers days, this role is about teaching, mentoring, and shaping young careers, not dealing with superstar egos or New York tabloids.
He also appears on NBA TV and Fox Sports, sharing sharp analysis from his years as a player, coach, and executive. Fans get to see something his critics often ignore: his deep understanding of the game.
Through the Mary’s Court Foundation, named after his mother, he funds education, anti-poverty efforts, and sports programs for Chicago youth. The foundation has awarded over 100 scholarships, often partnering with Indiana and UC Berkeley—schools that helped shape his own journey.
He works with Chicago’s mayor on Windy City Hoops, giving kids safe places to play. He serves on the Cannabis Trade Federation’s DEI task force, blending his business interests with social justice.
On social media, he shares family moments, motivational posts, and his take on basketball. He lives in Los Angeles with his wife Lynn, whom he married in 1985. Their kids—Joshua and Lauren—have their own careers in consulting and recycling, respectively. Isiah also maintains a relationship with his son Mark from a previous relationship, despite early legal battles.
After decades of chaos, controversy, and constant reinvention, his life is quieter now—but no less impactful.
Legacy in Conflict
This is the paradox of Isiah Thomas.
On one side:
The CBA collapse
The Knicks disaster
The harassment scandal
The FIU controversies
Feuds with Stephen A. Smith, Michael Jordan, and more
On the other side:
One of the greatest point guards in NBA history
A kid from Chicago’s West Side who built a $100 million business empire
A mentor to younger players like Jaylen Brown
A builder of real estate, environmental, and cannabis companies
A philanthropist changing lives in the same kind of neighborhood he grew up in
In 2024, Isiah told The Athletic:
“If I’m only remembered for basketball, I failed at life.”
Maybe that’s the heart of his story.
Stephen A. Smith sees a trail of executive mistakes, scandals, and broken organizations.
Isiah Thomas sees a journey—from poverty to championships, from failure to reinvention, from broken systems to new opportunities.
Somewhere in the middle lies the truth:
a brilliant, flawed, relentless competitor who refused to let his worst chapters define his final legacy.
And as long as Stephen A. Smith has a microphone and Isiah Thomas has an opinion, this story?
It’s far from over.
