If you mention that MJ was 6 out of 6 in the Finals in front of Shaq, he will be quick to point out that his team was the last one to beat the mighty Bulls in the playoffs. In 1995, MJ returned and led the Bulls to the playoffs. After defeating the Hornets in the first round, they lost to the hottest young team in the NBA.

Shaq and Penny were THE duo of the future, a tandem ready to take the league by storm. But in 96, Shaq’s contract was up, and Orlando messed it up. Some context for you – the salary cap in 1996 was $24 million. There are 46 players in the NBA who are getting paid more than $24 million this year; Harrison Barnes is at $24.1 million in Sacramento.

There were other significant differences: there was no maximum salary provision and no luxury tax penalty. Teams could exceed the cap to re-sign its own player (and suffer no extra tax), while other teams had to sign that player under the salary cap. The advantage of teams keeping their stars was enormous. So how did Orlando mess this up?

First of all, they started to low-ball Shaq. They probably felt their advantage over other teams was so high that they could try and get him with a relatively low offer. Alonzo Mourning drafted no.2 right after Shaq in 1992, had just signed a seven-year, $105 million deal. That set the market, and Shaq made it clear – he needs to get more than Mourning. The number was set around $20 million per year.

The Magic came in with four years, $54 million. There’s low-balling, and then there’s insulting; you can guess how Shaq felt about this. But this wasn’t unheard of, teams starting low fully aware the offer will have to go up. What followed was the first major mistake the Magic did.

“The more baffling part of the call, and I’ll never forget this, was that the Magic, I guess in an attempt to create some kind of leverage, actually criticized O’Neal’s rebounding and defense. Are you kidding me? When you have a player of Shaq’s caliber, a guy who in his first four years in the league had already won Rookie of the Year and a scoring title, been named to the All-NBA team three times, been a runner-up for league MVP and led Orlando to the Finals after knocking off Michael Jordan, you tell that guy he’s the greatest thing since sliced bread. You bend over backwards to get a deal done with him. Instead, the Magic decided it was a good time to criticize major parts of Shaq’s game?” Joel Corry, CBS Sports

Shaq told his agents to get him other offers and had two conditions. They had to find a team that can offer him a 9 million under the cap without gutting the roster to offer a seven-year, $100 million contract voidable after three years, and preferably for that team to be in a big market. The teams that made some sense at the start of the process were the Knicks, Pistons, Heat and the Hawks. All had a way to make it happen but made other moves that prevented any serious conversations. Enter Jerry West.

The first brilliant thing the Lakers did was to trade Vlade Divac for Kobe Bryant. Not just because it was Kobe Bean Bryant, but because they saved $3 million of cap space in the deal! They offered $95.5 million over seven, but Shaq rejected it as it was still lower than what Mourning got in Miami. Orlando got a second chance.

OK, things got serious, and it was time for the Magic to blow everyone out of the water and lock Shaq up. They low balled again, offering contracts with incentives everyone knew were not likely, such as Shaq shooting over 60% from the free-throw line. To add insult to injury, they made their final mistake.

“The Orlando Sentinel conducted a poll asking whether Shaq was worth $115 million. At that time, you could’ve asked that question about any player in the NBA, probably including Jordan, and fans would’ve said no, and sure enough, over 90 percent of the some 5,000 people who responded didn’t feel Shaq was worth the money.” Joel Corry, CBS Sports

Shaq had enough, and Jerry West seized the moment. The Lakers made additional moves and offered $120 million over seven years. A dynasty was born. This is the business side of basketball that players talk about, while lucrative can get very personal and painful. Years later, Shaq summed it up like this.

“I hate the business of basketball. They need to change the rule that whoever drafts you, you gotta stay with them your whole career. My first four years there were probably the best years of my life.” Shaquille O’Neal

This is obviously hyperbole from the Big Diesel, but it goes to show how much he loved playing in Orlando and wanted to stay there. After winning in LA and Miami, having an illustrious NBA career, and being on the best show on TV, Shaq still misses his days with Penny. The Magic truly messed this one up.