The Parable of Scottie Pippen

Three leadership lessons inspired by Scottie Pippen

Best known for his role as Michael Jordan’s accomplice on the dominant 1990s Chicago Bulls teams, Scottie Pippen is a classic study in leadership. And, Shakespeare.

Every Shakespearean story includes a main character with one incredible attribute that turns inside out over the course of the drama. The attribute evolves into a tragic flaw that eventually destroys him.

Scottie Pippen was not destroyed. Heck, he wasn’t even the main character. But, Scottie had a unique capacity for greatness; attributes, flaws, and all.

In my youth, Scottie was always a bit of a mystery to me as I watched him playing alongside Jordan. Scottie didn’t say much, but he did so much.

I was reminded of all of this as I watched ESPN’s The Last Dance, the penultimate documentary series about the six-time championship-winning 1990s Chicago Bulls. The Bulls’ matriculation into NBA dominance coincided with my own coming of age. The documentary series took me back to my youth. They reminded me how important that time was for me and how important sports figures can be for setting expectations for excellence, leadership, and righteousness.

Scottie Pippen is the sort of person we can all take notes on and grow from.

Dueling Ego

As I wrote in my previous post, It Takes Two, Scottie is known as the perennial #2 to Michael Jordan’s #1. He took being a two-man to the next level and really set a standard not seen since his era. Scottie was a rare blend of strong ego and strong support. He was strong enough to believe that he could win a championship and that he could compete alongside the best players in the world, including his iconic teammate, Michael Jordan.

Despite his confidence, his talent, and his aggressiveness on the court, Scottie kept his ego in check as it relates to playing with Michael Jordan. The ups and downs of championship-caliber basketball never affected Scottie’s perspective as a two-man as long as Jordan was on the court. He never got out of pocket as a #2 in all the years they played together.

Scottie’s competitive ego and his complimentary ego existed in the same place and time, in a way physical matter never could.

Leadership lesson: Be your absolute best and recognize when someone else is better.

Honest

Sometimes it feels like Scottie is honest with everyone except himself. First, he said he was happy to serve as the team’s facilitator and ultimate utility player, then he decided to sit himself out during one of the team’s most pivotal games during the 1994 playoffs.

When I think of Scottie Pippen, I think of a shoulder shrug. He is the poster guy for the phrase, “it is what it is.” A small-town guy, Scottie played like a mute. He didn’t say a lot, but what he did was earnest. He was generally known as a nice guy who was good to play with and easy to respond to.

That’s because Scottie is honest. Too honest at times. He has become a minor pop-culture figure, at least among basketball fans — because when he does speak he is bold and sometimes brash about the game he loves, about Jordan and the Bulls, and about himself.

The truth of the matter — according to Scottie himself — is that serving as the #1 team leader when Jordan briefly retired was the most fun he had during his career. He felt respected and he enjoyed leading the team in his style. But, when the moment of truth came, he wasn’t strong enough to make the right decision for the team. He knows that.

Leadership lesson: Being truly honest with your team requires you to be honest with yourself. Be honest about what you can and cannot live with….and without.

Mistakes

Scottie’s unique brand of honesty has made him transparent and relatively easy to understand. He speaks his mind and he owns his mistakes of the past, so much so that he says he would make the same mistakes again. Weird, but okay Scottie.

Over the years, Scottie was upset with the team owner and general manager for not doing enough to honor his contribution to the team. However, much of his frustration was found in his 1991 decision to sign a long seven-year contract extension during his prime years. That contract is largely known to be a horrible contract, but Scottie was dead-set on doing it his way. He did not take the advice of the people around him. By 1997 he was an NBA legend with a rookie-ish contract.

Scottie’s honesty is our portal to understanding him and, more importantly, understanding how phenomenal people can make colossal mistakes.

Leadership lesson: Some mistakes are preventable. You will have times when you are upset, emotional, and perhaps want to go over the edge. Don’t do it. Listen to the people you trusted yourself enough to surround yourself with. They can save your life, your treasure, and your reputation in crucial moments.

All in all, Scottie’s place is firmly affixed in the NBA firmament. He is a bonafide hero of a legendary squad. And, we should honor that.

We should also honor his contributions to us as a full person with out-sized ups and downs that we can all learn from.

I am an essayist, marketer, and strategist based in Birmingham, Alabama. Let’s stay connected via @HonestlyEd on LinkedIn, Medium, or Instagram. Or, just Buy Me A Coffee.

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