At the time, a young Scottie Pippen was widely expected to sign a massive deal at the end of his rookie contract, having blossomed into a rising star with the Bulls.
Instead, Chicago managed to lock him down long-term at a bargain-basement price.
But how? And how did they get away with it for so long?
The answer to that question makes for a fascinating tale, some of which was covered in The Last Dance.
Pippen’s problems all stemmed from his decision to extend his rookie contract two years before it was due to expire, something which isn’t even possible in today’s NBA.
By negotiating his new deal so early, Pippen didn’t have any of the leverage that would’ve worked in his favour if he’d waited until his existing contract had expired.
But Scottie was determined to sign an extension as soon as possible because he was working to support his father and brother, but of whom were in wheelchairs.
For all he knew, he could get injured at any moment and lose all his earning power overnight, and his dad and brother were counting on him.
So Pippen signed off on what was effectively a seven-year, $18 million contract.
Pippen’s agents advised him against taking it, according to The Undefeated’s Marc Spears, and Bulls owner Jerry Reinsdorf even says he told Pippen that he’d regret locking himself into such a lengthy contract.
Just about everyone knew it was a bad deal for Pippen at the time.
However, no one could’ve predicted just how much worse it would become.
The NBA’s salary cap more than doubled between Pippen signing his extension in 1991 and his departure from the Bulls in 1998, jumping from $11.9 million to $26.9 million in that period.
So, not only had Pippen negotiated without leverage, he’d done so using outdated metrics.
It’s worth pointing out that he was still the NBA’s 16th highest-paid player when his new deal first kicked in.
That wasn’t too bad at all in the moment, considering Pippen wasn’t an All-Star yet.
But his contract proceeded to age about as poorly as Macaulay Culkin.
The more the cap increased, the worse Scottie’s deal looked.
By the time Pippen’s final Bulls season arrived, he was the sixth-highest paid player on the team and the 122nd highest-paid player in the league.
Dennis Rodman, Toni Kukoc and Ron Harper all earned about 70 percent more than Pippen that year.
Luc Longley was taking home more than him too.
Meanwhile, Michael Jordan’s $33.1 million salary was almost 12 times larger than Pippen’s, which sat just below $2.8 million.
To make matters worse, Pippen was heavily responsible for the very salary cap spike that screwed him.
The dramatic cap increase was only possible because of the immense popularity and revenue that his Bulls brought to the league with their spectacular play.
While Magic Johnson and Larry Bird first put the NBA on the map, it was the 90’s Bulls which really catapulted the NBA to previously unthinkable heights.
That popularity translated to unprecedented TV deals for the league, which resulted in huge paydays for the players.
And yet one of the men most responsible for the league’s financial boom didn’t see a single dollar added to his existing paycheque.
Pippen tried to renegotiate his deal over the years, but Bulls management never budged.
They had one of the best value contracts in the history of sports and they weren’t about to ruin it.
Pippen’s fractured relationship with management could have derailed the Bulls dynasty altogether, but thankfully, it never quite came to that.
In the end, he was at least able to sign a hefty five-year, $67 million deal with the Houston Rockets after leaving the Bulls in 1998.
And down the road, the Bulls even gave him a two-year, $10 million deal to finish his career in Chicago.
Having made more than $100 million across his career, Pippen understandably won’t get a whole lot of sympathy from most regular, everyday people.
And if he was earning anywhere near the amount of money he deserved, the Bulls would’ve had a much harder time adding a championship-level supporting cast around him and Jordan, let alone a historic dynasty.
But for Pippen, none of that took the sting out of spending the most profitable years of his life earning a fraction of what he was worth, purely because he was trying to look out for his wheelchair-bound loved ones.