With the second episode of ESPN’s “The Last Dance” focusing on the behind-the-scenes drama involving Scottie Pippen, there’s been a lot of talk about the seven-year, $18 million contract extension that he signed in 1991 and whether the Chicago Bulls should have restructured his deal.
Since I was a certified NBA agent back then, I wanted to share my thoughts on the situation.
First of all, the Bulls could’ve restructured Pippen’s deal. In today’s NBA, teams typically can’t restructure a player’s contract; the only exception is if the player is extended and the team has cap space. But back in the 1990s, the Bulls could have ripped up Pippen’s contract and given him a new deal as long as they were under the cap. Considering how big of a role he played in Chicago’s dynasty, you’d think the Bulls would have done this. Back then, teams ripped up contracts all the time, so it blows my mind that the Bulls refused to give in.
Scottie was one of the best players in the NBA and he was absolutely underpaid, so they should have recognized his value and restructured his deal. I definitely understand why Scottie was upset.
Some context is important: As Scottie mentioned in “The Last Dance,” his father and brother were both paralyzed, and he has 11 siblings. It seems that one of Scottie’s top priorities was taking care of his family, which is likely a big reason why he agreed to the extension. When he initially signed that extension in 1991, I’m sure it was a relief knowing that his NBA paychecks would keep coming for five more years. He wanted long-term security, and I respect that he looked out for his family.
When he signed the extension, I remember being surprised. He played really well as a rookie and I thought he was more valuable than that. But it is important to note that the deal didn’t seem too bad in the early years. In 1992-93, only seven players in the NBA earned more than Pippen, so he was properly compensated. When the NBA’s new Collective Bargaining Agreement caused the salary cap to rise in 1995, other stars were able to hit free agency and get a substantial raise, but Pippen was stuck on the same deal. That was the issue.
However, Pippen had no way of knowing that a new CBA would cause this drastic change. He also had no way of knowing that he would go on to become one of the NBA’s best players and help the Bulls win multiple championships. Hindsight is 20/20. In recent years, we’ve seen similar situations play out. Players who locked themselves into a long-term contract in 2015 were kicking themselves when the cap spiked one year later due to the NBA’s new TV deal.
I’ve seen some people ask: Why didn’t Pippen try to get a player option in his contract? The Bulls and owner Jerry Reinsdorf were adamantly opposed to giving out player options at that time, so there’s no way Pippen could’ve gotten one.
There have been several reports that Pippen’s agents, Jimmy Sexton and Kyle Rote, tried to persuade him not to sign the extension, but he chose to take it anyway. Even Reinsdorf says he tried to talk Pippen out of inking the deal, but Pippen wouldn’t budge. As an agent, it’s our job to inform our client of their options and advise them, but we can’t make a player do anything.
If I had been representing Pippen back then, I would’ve explained why such a long extension was risky and advised him not to sign it. I would’ve stressed that in meeting after meeting. But if he still wanted to take the deal, there’s not much that an agent can do. It can be very frustrating when you don’t agree with a decision that your client is making, especially when you know that it could come back to bite them later. But we work for the player and, at the end of the day, it’s their contract and their life.
If I knew that there was no convincing Pippen otherwise, I would’ve sat down with him and tried to understand why he felt so compelled to sign the extension. Maybe he had a really good reason or there were serious issues that necessitated this; we don’t know. If Pippen was adamant about signing the deal and couldn’t be persuaded, all you can do as an agent is try your best to understand, be supportive and try to find other ways to help the client.
And, from what I understand, Sexton and Rote did a good job of lining up endorsement opportunities for Scottie, especially after the Bulls started winning championships, and Pippen became a household name (so he was able to strike when the iron was hot in that regard).
“The Last Dance” also touches on the fact that Pippen was constantly popping up in trade rumors, which also upset him. When my players are surfacing in the rumor mill, I tell them not to pay attention to any of that. There are so many rumors and only a small fraction become serious talks and actually mean something. Most trade rumors come and go. You’re a pro and you need to stay ready and focused at all times, so you can’t get caught up worrying about that stuff. Also, showing up in trade rumors just means that a number of teams are calling about you and want you. It’s flattering, really. That’s the way you have to look at it. And if you do get traded, go kick a** for your new team! They wanted you enough to give up assets to bring you in, so go make the most of your new situation. That’s what I tell my players.
Despite Pippen’s frustration, he ended up doing really well for himself, earning over $107 million from his NBA contracts throughout his career (thanks in large part to his deals with the Houston Rockets and Portland Trail Blazers).
In fact, Pippen actually ended up earning more than Michael Jordan, so it’s safe to say everything worked out for him in the end.
Torrel Harris of Unique Sports Management has been a certified NBA agent since the late 1980s. Throughout the 1990s, Harris’ client list included George Gervin, Lewis Lloyd, Greg Foster and Cliff Robinson among others. Today, he represents players such as Tobias Harris (his son) and Kelly Oubre Jr.
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