The Diary of Isiah Thomas, Part I

There’s a reason why the Hall of Fame point guard-turned-industry mogul and TV analyst keeps boosting his net worth. Why he keeps embracing tasks of financial, social, educational or athletic significance while investing in people and places that most entrepreneurs with a simple interest in the dollar bill bottom line, wouldn’t dare touch.

Isiah Lord Thomas was the youngest of nine brothers and sisters and grew up impoverished on the crime-ridden West Side of Chicago in the 60s and 70s.

He says every accomplishment he has accumulated to this day is a product of the parenting of his mother Mary, who lived by a strict moral standard in a time of complete community chaos.

During our long chat at the New York Liberty offices in Tarrytown earlier this month, the first-year team President and former NBA titan recalled an incident during his recruiting process (out of St. Joseph High School in Illinois) that reveals his mother’s true character and really set the tone for his never sell-out approach as he matured into adulthood.

“My son’s not for sale”

Thomas: A recruiter came to the house and presented a briefcase and laid it on the table. He went through his recruiting spiel and said, Mrs. Thomas. This is for you and your family if your son will sign the papers.

So we opened up the briefcase and there was $50,000 in the briefcase.

We were jumping up and down. Again, we had no food. No lights. Yes, I’m coming to your school. Yeah..dude..I was like where do I sign? My brothers were hugging each other and we were all so happy. That went on for like a good minute. But then, you know how there’s that one person in the room that ain’t smiling? Its mama. Then you look over and you have to catch yourself because she isn’t smiling and then you say to yourself, O.K. Junior I guess you better sit back down.

So we sit down and I’ll never forget it…My mama closed the briefcase, pushed it back. Looked over at the coach, then looked at me and said,  “My son’s not for sale.”

It wasn’t a matter of him selling me short. She wasn’t selling me at all. That was such a powerful moment and a powerful message for me, my brothers, and my family. We are not for sale, no matter how dire our financial standing is. Our souls are ours. You as a person and individual are priceless. There’s no price for you and that was powerful.

The General Assumes Responsibility For Chi-Town’s Prince of Pill

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Thomas: Coach Knight came after that and the only thing he said was, There’s three things I’m going to promise you and your son. He’s going to get an education. He’ll be a gentleman. And I’ll teach him everything I know about the game of basketball.”

And then my brothers were like, I guess we ain’t going to Indiana (laughter).”

Then I saw a little twinkle in my mom’s eye and I knew we were in trouble. You know how some kids announce at a press conference which college they are attending? On the day of the announcement, she tapped the podium, got everybody’s attention, and said, My son has decided that he’s going to Indiana University to play for Bob Knight.

That’s basically how it went down. My moment in the spotlight would have to wait.

Indiana Legend

But not too long because Thomas was a sensation at Indiana, winning a National Championship with the Hoosiers in the 1980-81 season as a sophomore and then joining the NBA Draft and getting selected by the Detroit Pistons with the No. 2 overall pick. Lord Thomas was a starting All-Star off the rip. His court vision and basketball I.Q. charted with the legends of the game. He attributes much of his maturation and his continued focus on education, even after leaving his mothers nest, to Knights fierce and fatherly coaching style

Thomas: If you look at Coach Knight’s graduation record and the rate at which his players graduated…I think he graduated 98 percent of his players in the 70s and 80s. You look at what college coaches are doing now in terms of graduation numbers and its alarming. And we were getting real degrees. We weren’t getting basket weaving degrees. We went to school for real and he was on you about doing that and also on you about being the best basketball player that you can be. You can do both. He was producing real scholar-athletes and that’s why my mom sent me there.

The Transformer

Perception is everything when defining the legacy of an individual. Too often a person’s inevitable failures are highlighted while their vast list of personal accolades are ignored as insignificant to the narrative.

When Isiah Thomas was reintroduced back into the MSG fold as New York Liberty President by his longtime friend and Knicks owner James Dolan back in May, Dolan, a long-time advocate of Isiahs often-overlooked attributes, had this to say:

Now, weve agreed that it is time for him to take a lead role with the team as president, and through his ownership interest, Dolan said in a statement. Hes an excellent judge of talent, and Im confident that he will put all of his energy and experience into making the Liberty a perennially competitive and successful team.

Dolan wasn’t lying.

Desperately needing a boost in leadership and after missing the playoffs the past two seasons and last having been to a WNBA Finals in 2002, Thomas The Transformer (as he’s come to be known in the business world, even if his unshakable sports moniker is that of undisciplined risk-taker and franchise obliterator) came in, made a flurry of roster moves, impressed his championship will on the organization and two months into the season the Liberty were in first place and relevant again.

By the end of this 2015 WNBA season, the Liberty sported the league’s best record and went from 0 to 100 real quick on the optimism meter.

Following a season in which the Liberty advanced to the Eastern Conference Finals before falling to the Indiana Fever in a hard-fought three-game series, Dolan reaffirmed his unwavering belief in Thomas, implying that they were two kindred spirits on HBO’s “Real Sports With Bryant Gumbel” in an October segment saying:

 “I think I’ve always understood him…I don’t know if I can explain it other than that there’s something inside of both of us that’s really quite similar: the tenacity, the stubbornness,” Dolan adds. “Isiah’s a guy who doesn’t believe in his limitations, and I’m a guy who doesn’t believe in his limitations.”

All of the threats by women’s advocacy groups to protest Liberty games and the negative press surrounding Isiahs return to NY, where he served as Knicks team president from December 2003 to April 2008 and went 56-108 in two seasons as their coach before being fired, didn’t amount to much, because Isiah is a success this time around.

It’s easy to kick a guy when he’s down. The 2007 lawsuit brought by former team employee Anucha Browne Sanders cost MSG over $11.5 million and added insult to a debilitated franchise that had become an eyesore on the court; smothering under huge contracts and no future plan for success.

The jury also levied $11.6 million in punitive damages against MSG, but not Thomas, who became a media battering ram and fall guy. He was labeled as the guy who sunk the Knicks into another decade of failure, lost control of the organization, and promoted an unhealthy working environment.

But when a beaten man gets up and shows his mettle, people tend to sympathize with him and appreciate his resolve. The Liberty players were the only obstacle to Thomas getting the gig and everything with them was peace. The past was the past and Thomas’ acumen as a basketball teacher is indisputable.

We came in and sat down with the team,” Thomas told The Shadow League earlier this month when I visited his New York Liberty offices in Tarrytown for a one-on-one exclusive, “and once we spoke and everyone was comfortable and they said what they needed to say about the situation and received the assurances they sought,  everybody was on the same page and we got to work.”

Thomas was in good spirits on this day, flashing his million-dollar smile with regularity and understandably so. In addition to the dramatic turnaround on the court, under Thomas, Liberty attendance is solid, profits are up and Thomas says he wants his players to stay connected to the community through marketing, appearances and supporting myriad causes from health to education to female empowerment.

Issues that connect with fans and show that The NY Liberty is not just a WNBA franchise but part of the fabric of the Big Apple’s robust entertainment scene and an extension of Manhattan’s surrounding communities. It’s the same recipe that endeared Thomas to the entire city of Detroit as a player.

We wanted to push the envelope and re-brand the Liberty as a new, fresh package, highlight our talent and increase our fan base, Thomas said.

Thomas explained how his intention was to be active behind the scenes, working closely with the Liberty’s marketing folk to hire a public relations firm and commemorate certain moments in franchise history like next season’s 20th Anniversary celebration. He’s also assisted players with game-refinement and dropped a few jewels on various Liberty guards when the moment allowed.’

One of his most immediate and impressive impacts was being able to get  29 of the team’s 34 games on TV (including games on MSG Network) the most since 2007.

He’s built a strong, experienced and well-balanced coaching staff consisting of his former Detroit Pistons teammate Bill Laimbeer (2015 WNBA Coach of the Year) and assistant coaches Katie Smith and former Knicks head coach Herb Williams.

Thomas has also ventured outside the traditional WNBA box and hired former star Liberty guard Teresa “T-Spoon” Weatherspoon as a director of player development. It’s the first position of its kind in league history.


Thomas: You can’t have a better ambassador for women’s basketball, with more energy, knowledge and love for the sport than T-Spoon. She embodies everything and every passion someone should have for this game. It was a no brainer to bring her in. She’s also a connection to the glory years of Liberty basketball and bridging the past with a new, exciting future.

The glory years Thomas references is when the franchise made three of its four Finals appearances (1999, 2000, 2002).

Thomas executive initiatives also included hiring a sports psychologist and career transition consultant to help the players prepare for life after basketball. His ingenuity, innovative tactics and fearlessness are on full display in his new role.

All of those things aside, just the firestorm of emotion that his presence and personality incites, has put a gossipy, Hollywood spotlight on a franchise that was fading into obscurity.

To Be Truly Great Is To Shine Magnificently and Suffer Excruciatingly

Isiah Thomas has a history as glorious and accomplished as it is tainted (whether fairly or unfairly). It’s littered with personal battles and struggles for respect and a deep concern for the conflicted and historically-challenging existence of African-Americans in this country. His basketball and business savvy receives far less intellectual praise than most business moguls of his ilk and social conscience get credit for.

However, winning and losing is part of the game and Thomas’ portfolio of life filled with basketball, business and contributions of socially redeeming value is stacked with both. In-between the criticism and accusations and biased public analysis of his worth as an individual; and regardless of how the media presents his story, theres a reason that Thomas is able to keep rising like a Phoenix.

 The Resilience of Education 

Most people dont have that Russian Roulette, Deadly Poker face. Ice water so cold running through their veins that it could freeze the nuts off a Polar Bear. Most people have a hard time coming back from a mistake or a failure or a loss. Largely because people dont have the mental fortitude to start from the bottom all over again, especially after achieving some level of success. Also, because of the way today’s wolfpack media can be so unforgiving, sensational, ignorant of the total truth or unwilling to admit when the narrative has shifted.

Those rare resilient types, like Isiah Thomas, are special people. He’s amassed a multi-million dollar business empire and is deeply involved in charity work. He deals with failure and success like any great human. He fearlessly rides the roller coaster of life with steel confidence embedded in his DNA from a mother who refused to compromise her principles or sell her kids short.

Over the course of a career in which Thomas has always shot for the stars, some pellets have struck his armor and left noticeable scars. Those scars, however, are mostly surface wounds that are visible to social media seekers of shocking headlines, gossip and fans of the tactical destruction of African-American world-changers.

He continues to enjoy underdog battles and investing in cement; trying to get a rose to grow out of concrete. After all, the underdog has the most challenging journey. When you are already expected to lose and the conditions are set for your failure, there is a brilliance in survival and a unique magnificence in overcoming those tremendous odds.

Thomas told The Shadow League that this philosophy applies to sports and life. He was an underdog growing up dirt poor in a struggling Chi-Town. Just another poor black boy. Same as the other kids from his hood. However, Thomas was that one-in-a-million golden child. Most of his neighborhood buddies are dead, having fell victim to crime, drugs, violence or the crushing effects of poverty and educational deprivation. Thomas says instead of talking about how bad things are, the focus should be on the guys that make it out of those almost impossible circumstances. How do we create more of those dudes?

Thomas: You can educate individuals while living in poverty, but when you put weapons and drugs on top of poverty, that individual almost has no chance…because the way our society works, it appears that in all communities, when you take away recreation; you close the libraries; you close the schools and then you substitute that with drugs and weapons; then that kid has almost no chance.

I say almost no chance because the question that should be asked is, How are these kids surviving and continuing to be educated, coming out of these situations. Not, Whats wrong with these kids? But, How are they doing it?

Thats what we should be looking at as opposed to studying whats wrong, because clearly all of the odds are stacked against them and still our communities are producing doctors, lawyers, journalists and they are still thriving and still coming. We have to focus on how and why and then apply those answers to everybody coming up short.

Now imagine if the playing field was leveled. What would these communities look like? That’s what I dream of every day. That’s the dream my mother shared and a reason why we both have streets named after us. There’s a street named after me in Detroit and Illinois and one in Illinois named after my mother.

Mary’s Memory Live On 

In 2010, Marys Court Foundation was established to try and help level that playing field a bit more. Mary’s Court is the family foundation of CEO  Thomas and his wife. Marys Court commemorates the life and legacy of Isiah’s mother, Mary Thomas, as a transformational agent of service to the economically disadvantaged. It strives to create a model for schools and communities that inspires academic success, promotes good health, encourages housing and economic development, and builds safe communities.

 Thomas: Mary’s court is going well. My mother was a pillar in the community and a servant in the community and her whole mission was trying to help others. What Marys Court does is, we try to help families strive or live while in poverty. We give assistance in education, housing, and healthcare needs.

Deadly Misconceptions: Innovator vs. Obliterator 

Thomas continues to take his fight for a better world straight to the gut of the inner-cities

In 2013, Thomas, an analyst for NBA TV and a confidant of Knicks owner James Dolan, worked with community leaders to organize two separate basketball tournaments for gang members during the apex of gun violence in Chicago and New York that drew negative national attention.  He also partnered with Chicago mayor Rahm Emanuel to create The Windy City Hoops Program, a weekend youth league in local parks to provide an alternative for at-risk teens, just one of his many anti-gang and pro-education initiatives.

Despite his selfless dedication to improving society,  public opinion on Thomas runs the gamut from revered legend to bad seed. It’s all a matter of perception.

Thomas is constantly criticized for his supposed failed CBA venture which ended in 2001 in bankruptcy, instead of being lauded for the audacity of the challenge and the way his innovative implementations became a model for today’s NBA in several ways.

Thomas launched partnerships with Enlighten Sports and the University of Colorado and the CBA. New websites allowed fans to watch live game webcasts, use live shot charts, chat with players and more. Thomas said the internet was an integral part of  the CBAs strategy to provide engaging and entertaining content for fans

Also, Thomas launched a partnership with to provide fans across the nation with personalized video highlights and scores, as well as be a portal for All-Star League voting.

Thomas was ahead of the game in understanding that streaming video would eventually become the main catalyst for the dissemination of news and entertainment content.

He’s been successful in so many business endeavors. As Chairman and CEO of Isiah International LLC, an investment holdings company, Thomas is also the owner of five companies: Isiah Real Estate, a development firm specializing in commercial properties; TAND Properties, a property management firm, private equity and asset management firm; Isiah Marketing, Advertising and Public Relations; and GRE3N Waste Removal. Thomas also co-owns the waste removals sister company, RE3 Recycling, with his daughter, Lauren. His other business investments include Popcorn Indiana, Pashas Restaurant in Miami, Southern Hospitality BBQ, and Sweetgreen

With his part-ownership of The Liberty still pending, Thomas continues to reconstruct the franchise from the inside out, while connecting with the community.

It’s obvious that Thomas’ dedication to education, community and self-improvement separates him from many of his peers. Thomas finished his college degree at Indiana University during the Pistons off seasons and received his Masters in Education from the University of California at Berkeley in 2013. At UC Berkeley, Thomas thesis examined the connection between education and sports, specifically how American society makes education accessible (or inaccessible) to black male college athletes.


With the Pistons, Thomas was a player representative for the National Basketball Players Association and went on to serve as Vice President. In 1988, the NBA players elected Thomas to serve as President of the NBPA, where he served through 1994. During his NBPA tenure, he helped establish four historic Collective Bargaining Agreements and pushed to raise the average NBA player’s salary, which increased from $300,000 to $1.8 million.

Isiah knows how to work the numbers, but no one is thanking him or crediting him publicly for those historic accomplishments.

I asked him if he felt that too few NBA players are pursuing degrees post-career. Was the way he valued education, despite signing a $1.6 million deal after two years of college ball, the reason for his post-career entrepreneurial success? Just having the scratch to purchase the CBA  or as Thomas adds, buy into The NY Liberty, is an accomplishment foreign to most people and worth a pat on the back.

Thomas: You can’t discount the education. So did education help me? One hundred percent. Do I give total credit to the education? No, but 90 percent of it. The more you know, the better decisions you make. They say experience is the best teacher and the only way you get experience is to roll up your sleeves and get in. Will you make some mistakes? Yes. Can you learn from those mistakes? Yes, but that’s part of education.

School wise, I guess I’m fortunate because I was able to get an education in the books and I was able to get a real street education. So growing up poor and understanding what they would call street game or street knowledge and then putting that with book knowledge and being able to separate the two without getting caught up in either one…you find yourself using different tactics and techniques depending upon the situation.

One of the things about growing up on the streets on the West Side of Chicago…the moment I walked out of my house…and I take three steps and I see a guy halfway down the block…I have to know immediately and access the situation to determine whether or not that guy means me harm or if he’s going to let me walk by. And if I make a mistake in judgement…you know the end result. So do I cross the street or do I walk by? Some days you read the situation and say they are alright, I can walk by.

So you take that same intellect and knowledge and walk into a board room. And the guy who is sitting there in the board room with a notebook; you can look at that guy and think to yourself, Does he mean me good? Or, Is he gonna let me walk by? (laughter).

So its a combination and a balance of both.

In fact, after listening to Isiah speak, I assessed that it was probably easier for Thomas to deal with the failures of any business decisions than most business moguls, because where he comes from, where death stands three feet from your doorstep, gaining and losing money “isn’t the end of the world”.  

Thomas: Keywords are, ” End of the world,” because if you make the wrong decision walking down the street, it could be the end of the world. Whereas in business, you just lost. It happens. There’s always a comeback.

And with every comeback, Isiah’s ambition, energy, and mental psyche is healed and enhanced. The narrative on his life is reopened for debate. Thomas’ latest accomplishment in weathering the threats of protest and the media outcry against his appointment as Liberty President and then turning the franchise from playoff outsider to title contender with the WNBA’s best record in one season, is an example of his growth and entrepreneurial passion. It also brings a great balance to the general opinion about who Isiah Thomas is as a person, a businessman, a leader, and a basketball mind.

Read “The Diary of Isiah Thomas, Part II” here.

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