The Bulls dynasty of the 1990s came to an end ahead of the 1998-99 season. After winning a whopping six NBA Championships in the decade, Michael Jordan retired, Scottie Pippen was traded to the Houston Rockets and Phil Jackson stepped away from basketball altogether. But what if I told you the great run of championships almost ended at four rather than six because in the summer of 1996  this was almost a reality. 

Michael Jordan was a free agent in the 1996 NBA offseason, looking to negotiate a new-one year “ballon” payment deal similar to that of his friend and New York Knicks center Patrick Ewing. For the 1995-96 season, the Knicks had Ewing on a balloon payment deal worth $18 million, which was the largest single-season deal in the NBA prior to Jordan. 

The ‘96 season ended in heartbreak for the Knicks as they lost to the Bulls in the Eastern Conference Semifinals, marking the second straight year they lost in the second round. Looking to finally get over the hump, the Knicks knew that signing Jordan would help them on two major fronts. First, it would've (obviously) benefitted the Knicks from an overall roster talent perspective since they would’ve been adding the reigning MVP. And on top of that, they would’ve been severely weakening their primary rival, a Bulls team that had already eliminated them from the postseason four times before 1996.

The Knicks were confident they could snag “His Airness” for a few reasons. Ewing and Jordan had a strong friendship, dating back to their college years. Ewing even had taken a recruiting visit to North Carolina as a rising freshman, in which he and Jordan got into an intense one-on-one pickup game that Ewing and Tar Heels coach Roy Williams remembers well. Their relationship strengthened over the years as they would become rivals throughout almost the entirety of their NCAA and NBA careers. 

Jordan was confident that he and Ewing could win an NBA title simply adding him to the roster the Knicks had, fitted with tough players like Allan Houston, Larry Johnson and Charles Oakley, another good friend of MJ. Longtime Chicago Tribune beat writer Sam Smith was all over the story that offseason and reported that the key to the Knicks efforts to sign Jordan was their deal with ITT-Sheraton and Cablevision Inc.

Cablevision had just extended their ownership of the Knicks and Madison Square Garden to 90 percent and Jordan’s agent David Falk was looking to find a way to get Jordan as much as he could from the Knicks and then make even more money on top of that through a series of lucrative sponsorship deals with the Sheraton Hotel chain, which was owned by ITT. It was reported by Smith that the structure of the deal may have been about $12 million from the Knicks and another $15 million or so from ITT/Sheraton Hotels. 

The story goes that David Falk had a now-infamous conversation with Bulls owner Jerry Reinsdorf in which the Bulls organization was given “one hour, maybe the rest of the day” to beat a significant, $25 million offer from the Knicks. 

And the Bulls did just that. 

Knowing that New York was serious and that Ewing and Jordan were friends, the Bulls went all-in, giving Jordan a one-year $30 million dollar contract, the largest balloon payment in NBA history, eclipsing the previous mark by $12 million. 

Was it all a bluff? Did Jordan really think he and Ewing could win a title? Just how close was MJ to becoming the main attraction at Madison Square Garden? The world may never know. 

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