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The Most Underpaid Professional Athlete of All Time?
Scottie Pippen

As a hard-core basketball fan who grew up watching the Bulls win 6 championships, I thoroughly enjoyed the first two episodes of ‘The Last Dance.’ They were nostalgic, and listening to Michael Jordan reminisce about the Bulls’ run was pretty cool. However, more compelling than the trip down memory lane was the business going on behind the scenes of the dynasty — the stuff fans did not see.

While the Bulls embarked on their final championship season, the organization was falling apart. From clashing egos to salary disputes, poor personnel management, and a lack of leadership in the back office, the Chicago Bulls organization was full of drama despite appearing, at least on the surface, that everything was well. 

The Bulls organization was toxic toward the end of the dynasty. Part of it had to with the fact the team’s number two, Scottie Pippen, was angry about his compensation. He felt under-appreciated.


How Scottie Pippen Became the Most Underpaid Player in NBA History

Heading into that final championship season, Scottie Pippen was a top-five basketball player on the planet. That said, he was the 122nd highest-paid player in the NBA. Pippen wasn’t even a top-five paid player on the Bulls! And he had no one to blame for his lack of compensation, but for himself. 

The part of this saga that I find interesting for entrepreneurs is Pippen’s personal circumstances dictated his decision-making process in business; and thus, his overall compensation. His personal circumstances — nothing to do with his athletic ability or dedication as a basketball player — led him to become one of the most underpaid professional athletes in the modern era.

Before I go any further, and to avoid sounding like a complete ass, it is admirable what Pippen did. I have a ton of respect for his selflessness. He limited his own financial upside to lock in his family’s financial security. At least that was his intent.


Scottie Pippen’s Backstory

Scottie Pippen was raised in Arkansas. He grew up with several brothers and sisters, and his family did not have much money. To make matters more challenging, as a kid, Pippen’s father was paralyzed. Shortly after that, one of his brothers was paralyzed too… 

I can’t even imagine the stress and financial challenges the Pippen family had to deal with after that. And living under such financial pressure most certainly impacted Scottie’s view of money, desire for security, and overwhelming drive to want to end his family’s struggle. 

So right after being drafted to the NBA, Pippen did something unusual for professional basketball players. He made sure his family would be taken care of forever by signing a long-term deal, before he was able to show his value at the NBA level (he actually signed two long-term contracts with the Bulls — both of which made him grossly underpaid). That desire to secure his family’s financial future inevitably cost him tens of millions of dollars.

As Naval recently tweeted, the optimal condition to be in (as an entrepreneur) is “slightly hungry.” 

Pippen was starving for financial security when he sat down at the negotiation table — an unfortunate mindset to have when negotiating a deal with shrewd businessmen. But his personal life/upbringing made him that way — and who can fault him?

Although it saved his family from any further financial struggle, the need to sign a long-term deal, early in his career, resulted in Pippen not making what he was worth. It put a ceiling on his earning potential. That drove him to anger. 

Uncharacteristically, his anger, which grew over the years as he witnessed less skilled players make substantially more money, drove him to verbally abuse some of the people he felt did him wrong — namely Bulls management. And he ended up letting his teammates down in the process.


Personal Life Impacts Professional ROI

The point is, I’ve seen a lot of great entrepreneurs have their personal lives crumble beneath them while building their business (substance abuse, divorce, issues with children). They think the stresses from their personal life won’t impact them professionally. They’re wrong. Only sociopaths can compartmentalize that well. 

Your personal life will impact the decisions you make in business.

When one side of your life is falling apart, or in a desperate state, it can have a profound and negative impact on the other, resulting in diminished returns.

I’m not saying that you must keep everything (personal and professional) perfect at all times… that’s impossible. But be cognizant of the impacts they have on each other.

Scottie Pippen’s overwhelming desire to solidify his family’s financial future ended up costing him tens of millions in compensation, and a ton of psychological grief. Of course, family is far more important than money. Far more important. But those entrepreneurs who think their personal life won’t impact their ability to perform as a professional (and vice versa) are sadly mistaken. The two are interconnected in every way. And one side of your life dictates how you make decisions for the other.  

Stay hungry,





PS – I’ve been an entrepreneur and angel investor for more than a decade. Along the way, I’ve learned a thing or two about building businesses that’ll probably help during your entrepreneurial journey. Subscribe to my newsletter below. Only my best content will land in your inbox.