Thomas became part owner and Executive Vice President of the Raptors after his retirement. However, he was forced out of the organization 4 years later over accusations that he inappropriately gave tickets to prospective draftees, and also over alleged inappropriate behavior around female staff members. The final straw was his attempt to take over majority ownership of the team, something he forgot to keep secret from the incumbent majority owner, who finally fired Isiah in 1998.

After beating MJ's Bulls in the playoffs for 3 straight years, the 4th try was not to be, and MJ's Bulls won a 4 game sweep over the Pistons in 1991. However, Isiah didn't get the memo about good sportsmanship, and pouted off the court with 7.9 seconds remaining, refusing to shake hands with any members of the Bulls.

After getting fired from the Raptors, Isiah became a lead game analyst for NBC's NBA coverage. Network execs quickly discovered that his inexperience and monotone voice led to an awful viewing experience, and they hired Bill Walton to "back-up" Isiah as a game analyst. After letting Isiah save some honor, they moved him to their studio team. Nor surprisingly, at the end of the year, Isiah was not asked back.

In 2000, Isiah became the head coach of the Indiana Pacers despite never having coached or assistent coached anywhere at any level (continuing his tradition of doing things he had no training for). The year before he arrived, the Pacers reached the NBA Eastern Conference Finals, losing in Game 7 on the final play of the game. In Thomas' 3 years as coach, the Pacers never made it out of the 1st round of the playoffs, and when Larry Bird returned as President in 2003, his first act was firing Thomas as head coach.

Michael Jordan was a rookie making his first All-Star game appearance in 1985. Jealous of MJ's popularity, Isiah led a team-wide freeze-out of the young guard, refusing to pass him the ball and preventing him from shooting during the game. How did MJ pay Isiah back for his warmth & kindness? By refusing to allow Isiah onto the 1992 Dream Tream, even though Isiah was regarded as one of the greatest players of the day. That's called a major grudge. Isiah made the Olympic team in 1980, but because of the US boycott, never played in an Olympic game.

Given how bad he screwed up the Knicks from simply the front office, Thomas was given additional responsibilities in 2006 when he became head coach in addition to his President duties. Thomas really stepped up his mismanagement at this point: acquiring Zach Randolph & Fred Jones in a trade, and signing players such as Jerome James and Jared Jeffries to full mid-level exceptions. However, his two most brilliant deals were to acquire Steve Francis and Stephon Marbury. Paying no attention to the usual belief that you don't want one me-first point guard with an ego the size of Brooklyn, Thomas went ahead and signed two of them, creating potentially the worst dollar-for-value backcourt in the history of the NBA.

Thomas bought the CBA in 1998 for $5M. 2 short years later, the league was forced into bankruptcy and folded. On Wall Street, that'd be called "a quick turnaround". Being the wise investor that he is, Thomas rejected an offer from the NBA for $11M to make the CBA the official minor-league of the NBA. Apparently Thomas was holding out for...I'm not sure what he'd be holding out for actually. The managers of the individual franchises blame the quick tanking on Thomas' mismanagement and reckless spending. Hard to believe, considering his complete lack of business/management education.

Upon completion of his fine work in Indiana, Thomas was immediately hired as President of the New York Knicks. In a little less than 3 seasons as President, Thomas managed to give the Knicks the highest payroll in the NBA combined with the 2nd worst record. To make matters worse, he tied up the Knicks salary cap in untradable players until 2012. He also traded away draft picks (in the top 5 given the Knicks' records) for players such as Eddy Curry.

In the sexual harrassment case that will be used by law school professors as the example of "what not to do" for 20 years, Thomas and his employer were sued by Enucha Brown Sanders, the Knicks Marketing executive, for sexual harrassment and resulting retaliation in 2006. Sanders won a decision of $11.6M, one of the largest sums paid out in history. Creating a welcoming and warm environment for everyone, Thomas was accused of calling Browne-Sanders a "bitch" and a "ho", then professing his love for her after a basketball game and attempting to kiss her. Showing his marketing/business savvy, Thomas responded to marketing requests by Browne-Sanders by saying "Bitch, I don't give a f* about the sponsors. I don't give a f* about ticket sales. Bitch, I don't give a f* about these white people". Yes, you won't find that response in any MBA Marketing book, I guarantee that.